Filter by chemistry class
Artemisinin 📖 Story
Library

Artemisinin

Antimalarial endoperoxide

Aspirin 📖 Story
Library

Aspirin

NSAID; COX inhibitor

Benzene 📖 Story
Library

Benzene

Prototypical aromatic; carcinogen; resonance icon

Caffeine 📖 Story
Library

Caffeine

Adenosine antagonist; stimulant

Capsaicin 📖 Story
Library

Capsaicin

Chili pepper TRPV1 agonist

Cortisol 📖 Story
Library

Cortisol

Stress glucocorticoid

Dopamine 📖 Story
Library

Dopamine

Reward; Parkinson's; catecholamine

Insulin 📖 Story
Library

Insulin

Peptide hormone; type-1 diabetes first-line

Morphine 📖 Story
Library

Morphine

Opioid analgesic

NAD+ 📖 Story
Library

NAD+

Redox cofactor (e- acceptor)

Penicillin G 📖 Story
Library

Penicillin G

First-line β-lactam

Acetylcholine
Library

Acetylcholine

Neuromuscular junction transmitter

Adrenaline (epinephrine)
Library

Adrenaline (epinephrine)

Fight-or-flight catecholamine

Alprazolam
Library

Alprazolam

Benzodiazepine; panic disorder

Amphetamine
Library

Amphetamine

CNS stimulant

Ascorbic acid (C)
Library

Ascorbic acid (C)

Antioxidant; collagen hydroxylation

Atorvastatin
Library

Atorvastatin

Statin; cholesterol lowering

Bisphenol A
Library

Bisphenol A

Polycarbonate + epoxy monomer; endocrine concern

Cannabidiol (CBD)
Library

Cannabidiol (CBD)

Non-psychoactive cannabinoid

Chloroform
Library

Chloroform

NMR solvent (CDCl3); former anesthetic

Cholecalciferol (vitamin D3)
Library

Cholecalciferol (vitamin D3)

Bone mineralization hormone

Cholesterol
Library

Cholesterol

Membrane sterol; hormone precursor

Cocaine
Library

Cocaine

DAT inhibitor; topical anesthetic

Dexamethasone
Library

Dexamethasone

Potent glucocorticoid

Diazepam
Library

Diazepam

Benzodiazepine; anxiolytic

Diethyl ether
Library

Diethyl ether

Classic solvent; former anesthetic

Estradiol
Library

Estradiol

Primary estrogen

Fentanyl
Library

Fentanyl

Synthetic opioid; potent

Fluoxetine
Library

Fluoxetine

SSRI; Prozac

Folic acid (B9)
Library

Folic acid (B9)

One-carbon transfer; DNA synthesis

GABA
Library

GABA

Inhibitory neurotransmitter

Glutamate
Library

Glutamate

Excitatory NT; NMDA/AMPA

LSD
Library

LSD

5-HT2A agonist psychedelic

MDMA
Library

MDMA

Empathogen-entactogen; ecstasy

Methamphetamine
Library

Methamphetamine

Potent CNS stimulant; controlled

Naloxone
Library

Naloxone

Opioid overdose reversal

Nicotine
Library

Nicotine

Tobacco alkaloid; nAChR agonist

Psilocybin
Library

Psilocybin

Psychedelic mushroom phosphate

Quinine
Library

Quinine

Antimalarial; tonic flavor

Serotonin
Library

Serotonin

Mood + sleep + gut motility

Sildenafil
Library

Sildenafil

PDE5 inhibitor; Viagra

Testosterone
Library

Testosterone

Primary androgen

THC
Library

THC

Cannabis psychoactive; CB1 agonist

Urea
Library

Urea

Wöhler's organic synthesis milestone; fertilizer

Vanillin
Library

Vanillin

Vanilla flavor compound

Warfarin
Library

Warfarin

Vitamin K antagonist anticoagulant

(-)-Menthol ·
Library

(-)-Menthol

Cooling sensation; mint

Amoxicillin ·
Library

Amoxicillin

Broad-spectrum penicillin

ATP ·
Library

ATP

Energy currency of cells

Atropine ·
Library

Atropine

Anticholinergic; mydriatic

cAMP ·
Library

cAMP

Second messenger

Ciprofloxacin ·
Library

Ciprofloxacin

Fluoroquinolone; DNA gyrase inhibitor

Clopidogrel ·
Library

Clopidogrel

P2Y12 antiplatelet

Codeine ·
Library

Codeine

Opioid analgesic; cough

Cortisone ·
Library

Cortisone

Inactive cortisol precursor; anti-inflammatory

Creatine ·
Library

Creatine

Muscle energy buffer

Curcumin ·
Library

Curcumin

Turmeric pigment; anti-inflammatory

Formaldehyde ·
Library

Formaldehyde

Simplest aldehyde; tissue fixative; resin

Haloperidol ·
Library

Haloperidol

Typical antipsychotic

Histamine ·
Library

Histamine

Allergic + gastric secretion

Isoniazid ·
Library

Isoniazid

Anti-tuberculosis

Melatonin ·
Library

Melatonin

Circadian rhythm regulator

Mescaline ·
Library

Mescaline

Peyote cactus phenethylamine

Niacin (B3) ·
Library

Niacin (B3)

NAD/NADP precursor

Ozone ·
Library

Ozone

UV-shielding allotrope; strong oxidizer

Phylloquinone (K1) ·
Library

Phylloquinone (K1)

Blood clotting carboxylase

Polyethylene (repeat) ·
Library

Polyethylene (repeat)

PE; world's most produced plastic

Prednisone ·
Library

Prednisone

Glucocorticoid anti-inflammatory

Progesterone ·
Library

Progesterone

Pregnancy hormone

Reserpine ·
Library

Reserpine

Antihypertensive; VMAT inhibitor

Resveratrol ·
Library

Resveratrol

Grape polyphenol; SIRT1 activator

Retinol (vitamin A) ·
Library

Retinol (vitamin A)

Vision; epithelial differentiation

Scopolamine ·
Library

Scopolamine

Anticholinergic; motion sickness

Sertraline ·
Library

Sertraline

SSRI; Zoloft

Strychnine ·
Library

Strychnine

Glycine receptor antagonist; convulsant

Sulfanilamide ·
Library

Sulfanilamide

First sulfa drug; folate inhibitor

Tadalafil ·
Library

Tadalafil

Long-acting PDE5; Cialis

Theobromine ·
Library

Theobromine

Chocolate alkaloid; mild stimulant

Thiamine (B1) ·
Library

Thiamine (B1)

Thiamine pyrophosphate cofactor

Thyroxine (T4) ·
Library

Thyroxine (T4)

Iodothyronine; metabolism

Zolpidem ·
Library

Zolpidem

Z-drug; sleep aid

[6]-Gingerol
Library

[6]-Gingerol

Ginger pungent compound

1-Bromopropane
Library

1-Bromopropane

Primary alkyl halide; SN2 substrate

1-Butanol
Library

1-Butanol

Biofuel candidate; lacquer solvent

1-Butene
Library

1-Butene

Polymer comonomer

1-Butyne
Library

1-Butyne

Terminal alkyne

1-Hexene
Library

1-Hexene

LLDPE comonomer

1-Pentanol
Library

1-Pentanol

Amyl alcohol; flavor solvent

1-Pentene
Library

1-Pentene

Terminal alkene; LDPE comonomer

1-Propanol
Library

1-Propanol

Primary alcohol solvent

1,2,3-Triazole
Library

1,2,3-Triazole

Click chemistry product (CuAAC)

1,3-Butadiene
Library

1,3-Butadiene

Synthetic rubber monomer; conjugated diene

1,3-Butadiene (BR monomer)
Library

1,3-Butadiene (BR monomer)

Synthetic rubber monomer

1,3,5-Triazine
Library

1,3,5-Triazine

Melamine + cyanuric acid core

1,4-Dioxane
Library

1,4-Dioxane

Cyclic diether solvent

2-Bromopropane
Library

2-Bromopropane

Secondary alkyl halide; SN1/E1 substrate

2-Butyne
Library

2-Butyne

Internal alkyne

2-Deoxy-D-ribose
Library

2-Deoxy-D-ribose

DNA backbone

2-Methylpentane
Library

2-Methylpentane

Branched C6 isomer

2,2-Dimethylbutane
Library

2,2-Dimethylbutane

Branched C6; gasoline component

2,3-Pentanedione
Library

2,3-Pentanedione

Buttery flavor; alpha-diketone

2,4,6-Trinitrotoluene
Library

2,4,6-Trinitrotoluene

Military explosive; symmetric aromatic trinitro

3-Methylpentane
Library

3-Methylpentane

Branched C6 isomer

4-Methyl-2-pentanone (MIBK)
Library

4-Methyl-2-pentanone (MIBK)

MIBK solvent

5-Hydroxymethylfurfural (HMF)
Library

5-Hydroxymethylfurfural (HMF)

Biomass platform chemical

7-Dehydrocholesterol
Library

7-Dehydrocholesterol

Vitamin D3 precursor in skin

Acenaphthylene
Library

Acenaphthylene

PAH with cyclopenta ring

Acetaldehyde
Library

Acetaldehyde

Ethanol metabolite; toxic intermediate

Acetamide
Library

Acetamide

Primary amide; plasticizer

Acetaminophen (paracetamol)
Library

Acetaminophen (paracetamol)

Analgesic + antipyretic

Acetic acid
Library

Acetic acid

Vinegar; archetypal weak acid

Acetic anhydride
Library

Acetic anhydride

Acetylation reagent; aspirin synthesis

Acetone
Library

Acetone

Simplest ketone; common solvent; nail polish remover

Acetonitrile
Library

Acetonitrile

Polar aprotic solvent; HPLC mobile phase

Acetophenone
Library

Acetophenone

Aryl methyl ketone; Friedel-Crafts product

Acetylacetone
Library

Acetylacetone

1,3-diketone; enol tautomer demo; acac ligand

Acetylene
Library

Acetylene

Welding gas; sp-hybridized; weak acid

Acridine
Library

Acridine

DNA intercalator; dye

Acrolein
Library

Acrolein

Burnt-fat odor; toxic α,β-unsaturated

Acrylic acid
Library

Acrylic acid

Acrylate polymers; super-absorbents

Acrylonitrile
Library

Acrylonitrile

PAN polymer; Michael acceptor

Acrylonitrile (PAN monomer)
Library

Acrylonitrile (PAN monomer)

Carbon-fiber precursor monomer

Adamantane
Library

Adamantane

Cage structure; diamond unit cell motif

Adenine
Library

Adenine

DNA/RNA purine base; pairs with T/U

Adipic acid
Library

Adipic acid

Nylon-6,6 monomer

Adiponitrile
Library

Adiponitrile

Hexamethylenediamine precursor

ADP
Library

ADP

ATP-1 phosphate form

Alanine
Library

Alanine

Methyl side chain

Aldosterone
Library

Aldosterone

Salt-regulating mineralocorticoid

Ammonia
Library

Ammonia

Haber-Bosch product; fertilizer feedstock; base

AMP
Library

AMP

Energy-low signaling nucleotide

Ampicillin
Library

Ampicillin

Aminopenicillin

Amylose (repeat unit)
Library

Amylose (repeat unit)

Linear starch component

Aniline
Library

Aniline

Aryl amine; dye industry foundation

Anisole
Library

Anisole

Methoxybenzene; activated aromatic

Anthracene
Library

Anthracene

Linear tricyclic PAH; fluorescent dye

Arachidonic acid
Library

Arachidonic acid

C20:4 ω-6; prostaglandin precursor

Arginine
Library

Arginine

Most basic AA; NO precursor

Asparagine
Library

Asparagine

Amide side chain; glycosylation site

Aspartame
Library

Aspartame

Artificial sweetener; Asp-Phe methyl ester; 200x sweeter than sucrose

Aspartic acid
Library

Aspartic acid

Acidic AA

Aziridine
Library

Aziridine

3-ring amine; alkylating warhead

Benzaldehyde
Library

Benzaldehyde

Almond aroma; aldol substrate

Benzimidazole
Library

Benzimidazole

Drug scaffold; PPI precursor

Benzo[a]pyrene
Library

Benzo[a]pyrene

Tobacco-smoke carcinogen; DNA adduct former

Benzofuran
Library

Benzofuran

Fused O-heterocycle

Benzoic acid
Library

Benzoic acid

Preservative E210; melting-point standard

Benzonitrile
Library

Benzonitrile

Aromatic nitrile; coordinative solvent

Benzophenone
Library

Benzophenone

UV blocker; photochemistry sensitizer

Benzothiazole
Library

Benzothiazole

Rubber vulcanization accelerator core

Benzothiophene
Library

Benzothiophene

Fused S-heterocycle; coal-tar

Benzoxazole
Library

Benzoxazole

Fused O+N scaffold

Benzyl alcohol
Library

Benzyl alcohol

Preservative; solvent; fragrance

Benzyl cation
Library

Benzyl cation

Resonance-stabilized benzylic cation

Benzyl chloride
Library

Benzyl chloride

Benzyl-cation stabilized; SN1/SN2 dual

Benzylamine
Library

Benzylamine

Primary benzylic amine

Berberine
Library

Berberine

Antimicrobial isoquinoline alkaloid

Biotin (B7)
Library

Biotin (B7)

Carboxylase cofactor

Biphenyl
Library

Biphenyl

PCB scaffold; heat transfer fluid

Bromobenzene
Library

Bromobenzene

Aryl Grignard precursor

Bromomethane
Library

Bromomethane

Methylating agent; fumigant

Butane
Library

Butane

Lighter fluid; LPG component

Butyl acetate
Library

Butyl acetate

Fruity solvent; coatings

Butyraldehyde
Library

Butyraldehyde

Butanal; perfumery

Butyric acid
Library

Butyric acid

C4:0; gut microbiome SCFA

Butyric acid
Library

Butyric acid

Rancid butter odor; gut microbiome

Caffeine (tea)
Library

Caffeine (tea)

Same as caffeine; tea origin

Calcium carbonate
Library

Calcium carbonate

Limestone; chalk; antacid

Camphor
Library

Camphor

Bicyclic terpenoid ketone; topical balm

Capric acid
Library

Capric acid

C10:0 MCT

Caproic acid
Library

Caproic acid

C6:0; goat milk

Caproic acid
Library

Caproic acid

Hexanoic acid; goaty odor

Caprolactam
Library

Caprolactam

Nylon-6 monomer

Caprylic acid
Library

Caprylic acid

C8:0 MCT; coconut

Carbazole
Library

Carbazole

OLED hole-transport material

Carbon dioxide
Library

Carbon dioxide

Greenhouse gas; combustion product; photosynthesis input

Carbon monoxide
Library

Carbon monoxide

Toxic gas; reducing agent; metal-carbonyl ligand

Carbon tetrachloride
Library

Carbon tetrachloride

Banned ozone-depleter; radical initiator solvent

Carvacrol
Library

Carvacrol

Oregano oil; antimicrobial

Carvone
Library

Carvone

Spearmint/caraway enantiomers

Catechol
Library

Catechol

1,2-dihydroxybenzene; redox-active

Celecoxib
Library

Celecoxib

Selective COX-2 inhibitor

Cellobiose
Library

Cellobiose

Two glucose β-1,4; cellulose hydrolysis

Cephalexin
Library

Cephalexin

First-gen cephalosporin

Cetirizine
Library

Cetirizine

H1 antihistamine

Chlorine
Library

Chlorine

Halogen oxidizer; water treatment; chlorination

Chlorobenzene
Library

Chlorobenzene

Aryl halide; SNAr substrate

Chloroethane
Library

Chloroethane

Ethylating agent; topical anesthetic

Chloromethane
Library

Chloromethane

Methylating agent; refrigerant

Cholic acid
Library

Cholic acid

Bile acid

Choline
Library

Choline

ACh + phospholipid precursor

Chrysene
Library

Chrysene

PAH; coal-tar component

Cinnamaldehyde
Library

Cinnamaldehyde

Cinnamon flavor

cis-2-Butene
Library

cis-2-Butene

cis isomer; geometric isomerism demo

Citral
Library

Citral

Lemon aldehyde

Citric acid
Library

Citric acid

Citrus acid; TCA cycle namesake

Corannulene
Library

Corannulene

Bowl-shaped PAH; buckybowl

Coronene
Library

Coronene

Hexagonal PAH; graphene fragment

Cubane
Library

Cubane

Cubic carbon framework; high strain

Cyanuric acid
Library

Cyanuric acid

Pool sanitizer stabilizer

Cyclobutane
Library

Cyclobutane

Strained 4-ring; puckered conformation

Cyclohexane
Library

Cyclohexane

Chair/boat conformation classic; non-polar solvent

Cyclohexanol
Library

Cyclohexanol

Nylon-6 precursor; ring-puckering demo

Cyclohexanone
Library

Cyclohexanone

Nylon precursor; lab solvent

Cyclohexene
Library

Cyclohexene

Diels-Alder substrate; bromination demo

Cyclopentadiene
Library

Cyclopentadiene

Diels-Alder diene; Cp- ligand precursor

Cyclopentane
Library

Cyclopentane

Envelope conformation; near-strainless

Cyclopropane
Library

Cyclopropane

Highly strained; banana bonds; former anesthetic

Cysteine
Library

Cysteine

Thiol; disulfide bond formation

Cytosine
Library

Cytosine

DNA/RNA pyrimidine; pairs with G

D-Erythrose
Library

D-Erythrose

Pentose phosphate pathway

D-Fructose
Library

D-Fructose

Fruit sugar; furanose form

D-Galactose
Library

D-Galactose

Milk sugar component; C4 epimer of glucose

D-Glucose
Library

D-Glucose

Primary blood sugar; pyranose form

D-Glyceraldehyde
Library

D-Glyceraldehyde

Simplest aldose; chirality reference

D-Limonene
Library

D-Limonene

Citrus monoterpene

D-Mannose
Library

D-Mannose

C2 epimer of glucose; UTI prophylaxis

D-Ribose
Library

D-Ribose

RNA backbone

D-Ribulose
Library

D-Ribulose

Calvin cycle ketose

D-Threose
Library

D-Threose

TNA backbone; primordial nucleic acid?

D-Xylose
Library

D-Xylose

Wood sugar; pentose

DCC
Library

DCC

Peptide-coupling dehydrating agent

Decalin
Library

Decalin

cis/trans-fused bicyclic; conformational analysis

Decane
Library

Decane

Kerosene component

DHA
Library

DHA

C22:6 ω-3; brain/retina

DHEA
Library

DHEA

Adrenal androgen precursor

Diacetyl
Library

Diacetyl

Buttery flavor; popcorn lung concern

DIBAL-H
Library

DIBAL-H

Partial-reduction of esters to aldehydes

Dichlorodifluoromethane (Freon-12)
Library

Dichlorodifluoromethane (Freon-12)

Banned CFC refrigerant

Dichloromethane
Library

Dichloromethane

DCM; common extraction solvent

Diclofenac
Library

Diclofenac

NSAID

Diethyl malonate
Library

Diethyl malonate

Malonic ester synthesis; alpha-anion source

Diethylamine
Library

Diethylamine

Secondary amine; rubber chemicals

Dihydroxyacetone
Library

Dihydroxyacetone

Glycolysis triose; self-tanner

Diisopropyl ether
Library

Diisopropyl ether

Peroxide-prone ether solvent

Dimedone
Library

Dimedone

5,5-dimethyl-1,3-cyclohexanedione; aldehyde test

Dimethyl carbonate
Library

Dimethyl carbonate

Green methylating agent

Dimethylamine
Library

Dimethylamine

Secondary amine; rubber accelerator

DIPEA (Hünig's base)
Library

DIPEA (Hünig's base)

Bulky non-nucleophilic base

Diphenhydramine
Library

Diphenhydramine

Sedating H1 antihistamine

Diphenylamine
Library

Diphenylamine

Antioxidant; OLED material

DMAc
Library

DMAc

Polar aprotic solvent

DMF
Library

DMF

Common polar aprotic solvent

Dodecane
Library

Dodecane

Diesel surrogate; jet fuel component

EDC·HCl
Library

EDC·HCl

Water-soluble peptide coupling reagent

Elaidic acid (trans-oleic)
Library

Elaidic acid (trans-oleic)

Trans-fat; cardiovascular risk

EPA
Library

EPA

C20:5 ω-3; fish oil

Epichlorohydrin
Library

Epichlorohydrin

Epoxy resin monomer

Ergocalciferol (vitamin D2)
Library

Ergocalciferol (vitamin D2)

Plant-derived vitamin D

Ergosterol
Library

Ergosterol

Fungal membrane sterol; antifungal target

Erucic acid
Library

Erucic acid

C22:1; rapeseed oil

Erythritol
Library

Erythritol

Sugar alcohol sweetener

Erythromycin
Library

Erythromycin

Macrolide; 50S ribosome

Ethane
Library

Ethane

Two-carbon alkane; natural gas component

Ethanol
Library

Ethanol

Beverage alcohol; fuel; solvent

Ethanolamine
Library

Ethanolamine

Phospholipid head group; CO2 scrubber

Ethyl acetate
Library

Ethyl acetate

Fruity solvent; nail polish

Ethyl formate
Library

Ethyl formate

Rum/raspberry flavor

Ethylamine
Library

Ethylamine

Primary amine; drug precursor

Ethylbenzene
Library

Ethylbenzene

Styrene precursor

Ethylene
Library

Ethylene

Plant hormone; polyethylene monomer

Ethylene glycol
Library

Ethylene glycol

Antifreeze; PET precursor

Ethylene oxide
Library

Ethylene oxide

Epoxide reagent; sterilant

Ethylenediamine
Library

Ethylenediamine

Bidentate ligand; EDTA precursor

Eugenol
Library

Eugenol

Clove essential oil; dental analgesic

Farnesol
Library

Farnesol

Sesquiterpene alcohol

Fluoranthene
Library

Fluoranthene

PAH; benzopyrene metabolic context

Fluorene
Library

Fluorene

OLED material scaffold; acidic CH

Formamide
Library

Formamide

Simplest amide; polar solvent

Formic acid
Library

Formic acid

Simplest carboxylic acid; ant venom

Fumaric acid
Library

Fumaric acid

trans-butenedioic; TCA cycle

Furan
Library

Furan

5-ring aromatic O-heterocycle

Furfural
Library

Furfural

From pentose dehydration; bio-refinery feedstock

Geraniol
Library

Geraniol

Rose + geranium oil

Glipizide
Library

Glipizide

Sulfonylurea; insulin secretion

Glucuronic acid
Library

Glucuronic acid

Phase II detox conjugation

Glutamic acid
Library

Glutamic acid

Acidic AA; MSG flavor

Glutamine
Library

Glutamine

Amide side chain; N storage

Glutaric acid
Library

Glutaric acid

C5 dicarboxylic; nylon precursor

Glycerol
Library

Glycerol

Triol; humectant; lipid backbone

Glycerol-3-phosphate
Library

Glycerol-3-phosphate

Triacylglycerol synthesis precursor

Glycine
Library

Glycine

Simplest amino acid; non-chiral

Glycine (NT)
Library

Glycine (NT)

Inhibitory spinal NT

Glycolic acid
Library

Glycolic acid

Alpha-hydroxy acid; skincare

Glycolide (PGA monomer)
Library

Glycolide (PGA monomer)

Bioabsorbable polymer monomer

Glyoxal
Library

Glyoxal

Dialdehyde; crosslinker

Grubbs II
Library

Grubbs II

Olefin metathesis catalyst

Guanine
Library

Guanine

DNA/RNA purine; pairs with C

Heparin disaccharide unit
Library

Heparin disaccharide unit

Anticoagulant glycosaminoglycan unit

Heptane
Library

Heptane

Octane-rating zero reference

Heroin
Library

Heroin

Diacetylmorphine; more lipophilic than morphine crosses BBB faster

Hexadecane (cetane)
Library

Hexadecane (cetane)

Cetane number reference

Hexamethylbenzene
Library

Hexamethylbenzene

Fully substituted benzene; X-ray reference

Hexamethylenediamine
Library

Hexamethylenediamine

Nylon-6,6 monomer

Hexane
Library

Hexane

Common organic solvent; oil extraction

Histidine
Library

Histidine

Imidazole side chain; enzyme catalysis

Hydrocortisone
Library

Hydrocortisone

Topical/systemic glucocorticoid

Hydrogen
Library

Hydrogen

Lightest element; reducing agent; clean fuel

Hydrogen chloride
Library

Hydrogen chloride

Strong acid in aqueous (HCl); gas in pure form

Hydrogen cyanide
Library

Hydrogen cyanide

Highly toxic; gold cyanidation

Hydrogen peroxide
Library

Hydrogen peroxide

Oxidizing agent; bleach; antiseptic

Hydrogen sulfide
Library

Hydrogen sulfide

Rotten-egg odor gas; toxic; weak acid

Hydroquinone
Library

Hydroquinone

1,4-dihydroxybenzene; photo developer; skin lightener

Hydroxyproline
Library

Hydroxyproline

Collagen-stabilizing modified AA

Hyoscyamine
Library

Hyoscyamine

Belladonna tropane alkaloid

Hypoxanthine
Library

Hypoxanthine

tRNA inosine base; gout pathway

Ibuprofen
Library

Ibuprofen

NSAID; analgesic

Imidazole
Library

Imidazole

His side chain; histamine; ionic liquid base

Indene
Library

Indene

Indenyl ligand precursor; coal-tar fraction

Indole
Library

Indole

Tryptophan + serotonin + IAA core

Iodobenzene
Library

Iodobenzene

Cross-coupling substrate

Iodomethane
Library

Iodomethane

SN2 substrate textbook; methylating reagent

Isobutane
Library

Isobutane

Branched C4; refrigerant

Isobutanol
Library

Isobutanol

Fermentation byproduct

Isobutylene
Library

Isobutylene

Butyl rubber monomer

Isobutyraldehyde
Library

Isobutyraldehyde

Branched C4 aldehyde

Isoleucine
Library

Isoleucine

BCAA; energy metabolism

Isooctane (2,2,4-trimethylpentane)
Library

Isooctane (2,2,4-trimethylpentane)

Octane-rating 100 reference

Isopentane
Library

Isopentane

Branched C5; ultra-low-T cryogen

Isophorone
Library

Isophorone

α,β-unsaturated cyclic ketone

Isoprene
Library

Isoprene

Natural rubber monomer; terpene unit

Isopropanol
Library

Isopropanol

Rubbing alcohol; lab solvent

Isoquinoline
Library

Isoquinoline

Alkaloid scaffold (papaverine)

Isoxazole
Library

Isoxazole

1,2-positioned O+N; drug scaffold

Jacobsen catalyst
Library

Jacobsen catalyst

Asymmetric epoxidation

L-Arabinose
Library

L-Arabinose

Plant gum pentose

L-Fucose
Library

L-Fucose

Deoxysugar; blood group antigen

L-Rhamnose
Library

L-Rhamnose

Plant deoxysugar

Lactic acid
Library

Lactic acid

Muscle fatigue; fermentation; PLA monomer

Lactide (PLA monomer)
Library

Lactide (PLA monomer)

Bio-PLA monomer; lactic-acid cyclic dimer

Lactose
Library

Lactose

Milk sugar; galactose-glucose

Lanosterol
Library

Lanosterol

Cholesterol biosynthesis branch point

Lauric acid
Library

Lauric acid

C12:0; coconut oil

LDA
Library

LDA

Hindered non-nucleophilic base

Leucine
Library

Leucine

BCAA; mTOR activator

Leukotriene B4
Library

Leukotriene B4

Inflammatory leukotriene

Levodopa
Library

Levodopa

Parkinson's dopamine prodrug

Levothyroxine
Library

Levothyroxine

Thyroid hormone replacement

LiAlH4 (LAH)
Library

LiAlH4 (LAH)

Strong hydride reductant

Linalool
Library

Linalool

Lavender essential oil

Linoleic acid
Library

Linoleic acid

C18:2 ω-6; essential

Loratadine
Library

Loratadine

Non-sedating antihistamine

Lysine
Library

Lysine

Basic AA; acetylation site

m-Xylene
Library

m-Xylene

meta-dimethylbenzene; isophthalic acid feedstock

Maleic acid
Library

Maleic acid

cis-butenedioic; resin monomer

Maleic anhydride
Library

Maleic anhydride

Diels-Alder dienophile; resin monomer

Malic acid
Library

Malic acid

Sour apples; TCA cycle

Malonic acid
Library

Malonic acid

Malonate ester synthesis backbone

Maltose
Library

Maltose

Two glucose α-1,4; starch digestion product

Mannitol
Library

Mannitol

Sugar alcohol; osmotic diuretic

MDI (PU monomer)
Library

MDI (PU monomer)

Polyurethane diisocyanate

Melamine
Library

Melamine

Plastic resin; protein-adulterant scandal

MeMgBr
Library

MeMgBr

Grignard methyl source

Menaquinone-4 (K2)
Library

Menaquinone-4 (K2)

Bone + arterial K vitamer

Menthone
Library

Menthone

Mint terpene ketone

Mesitylene
Library

Mesitylene

1,3,5-trimethylbenzene

Metformin
Library

Metformin

Antidiabetic; AMPK activator

Methacrylic acid
Library

Methacrylic acid

PMMA precursor

Methane
Library

Methane

Simplest alkane; natural gas main component

Methanol
Library

Methanol

Simplest alcohol; toxic; antifreeze; fuel

Methionine
Library

Methionine

Start codon; methyl donor (SAM)

Methyl acetate
Library

Methyl acetate

Pleasant odor solvent

Methyl ethyl ketone (MEK)
Library

Methyl ethyl ketone (MEK)

Industrial solvent; lacquer

Methyl salicylate
Library

Methyl salicylate

Wintergreen oil; topical analgesic

Methyl tert-butyl ether (MTBE)
Library

Methyl tert-butyl ether (MTBE)

Gasoline oxygenate; extraction solvent

Methyl vinyl ketone (MVK)
Library

Methyl vinyl ketone (MVK)

Michael acceptor textbook

Methylamine
Library

Methylamine

Simplest primary amine; fishy odor

Methylcyclohexane
Library

Methylcyclohexane

Axial vs equatorial conformer demo

Methyllithium
Library

Methyllithium

Methyl carbanion source

MMA (PMMA monomer)
Library

MMA (PMMA monomer)

Acrylic glass monomer

Morphine (alkaloid view)
Library

Morphine (alkaloid view)

Opium poppy alkaloid

Morpholine
Library

Morpholine

O+N heterocycle; corrosion inhibitor

Myrcene
Library

Myrcene

Hops + cannabis monoterpene

Myristic acid
Library

Myristic acid

C14:0; nutmeg

N-Acetylglucosamine (chitin unit)
Library

N-Acetylglucosamine (chitin unit)

Chitin/insect exoskeleton monomer

N-Acetylneuraminic acid
Library

N-Acetylneuraminic acid

Cell surface; virus binding

n-BuLi
Library

n-BuLi

Strong base + alkyl carbanion source

NaBH4
Library

NaBH4

Mild hydride reductant

Naphthalene
Library

Naphthalene

Bicyclic PAH; mothballs

Naproxen
Library

Naproxen

NSAID; long-acting

Neopentane
Library

Neopentane

Highly branched C5; tetrahedrally symmetric

Nitric acid
Library

Nitric acid

Strong oxidizing acid; nitration source

Nitrogen
Library

Nitrogen

Atmosphere main component; inert gas

Nitroglycerin
Library

Nitroglycerin

Explosive plus vasodilator; releases NO for angina

NMP
Library

NMP

Battery slurry + Li-ion solvent

Nonane
Library

Nonane

Mid-distillate hydrocarbon

Noradrenaline
Library

Noradrenaline

Stress catecholamine

Norbornane
Library

Norbornane

Bicyclic[2.2.1] scaffold; bridge-bond textbook

o-Cresol
Library

o-Cresol

Disinfectant; resin component

o-Xylene
Library

o-Xylene

ortho-dimethylbenzene; phthalic acid feedstock

Octane
Library

Octane

Gasoline component

Olanzapine
Library

Olanzapine

Atypical antipsychotic

Oleic acid
Library

Oleic acid

C18:1 ω-9; olive oil

Omeprazole
Library

Omeprazole

Proton pump inhibitor

Oxalic acid
Library

Oxalic acid

Dicarboxylic; calcium binder; rhubarb

Oxalyl chloride
Library

Oxalyl chloride

Swern oxidation activator + acyl chloride prep

Oxazole
Library

Oxazole

O+N 5-ring; natural product scaffold

Oxetane
Library

Oxetane

Strained 4-ring ether; drug discovery motif

Oxygen
Library

Oxygen

Oxidizer; combustion; respiration

Oxytocin
Library

Oxytocin

Cyclic nonapeptide with disulfide; labor and social bonding hormone

p-Xylene
Library

p-Xylene

para-dimethylbenzene; PET feedstock

Paclitaxel
Library

Paclitaxel

Anticancer taxane; microtubule stabilizer

Paclitaxel
Library

Paclitaxel

Microtubule stabilizer; anticancer

Palmitic acid
Library

Palmitic acid

C16:0 saturated; palm oil

Pantothenic acid (B5)
Library

Pantothenic acid (B5)

CoA precursor

Papaverine
Library

Papaverine

Isoquinoline alkaloid; smooth muscle relaxant

Penicillin G
Library

Penicillin G

First mass-produced beta-lactam antibiotic; inhibits PBP

Pentaerythritol
Library

Pentaerythritol

PETN explosive precursor; resin polyol

Pentane
Library

Pentane

Low-boiling solvent; foam blowing

PET repeat
Library

PET repeat

PET soft-drink bottles

Phenanthrene
Library

Phenanthrene

Angular tricyclic PAH

Phenol
Library

Phenol

Weakly acidic OH; antiseptic origin; resin monomer

Phenylacetylene
Library

Phenylacetylene

Sonogashira coupling substrate

Phenylalanine
Library

Phenylalanine

Aromatic; tyrosine precursor

Phloroglucinol
Library

Phloroglucinol

1,3,5-triol; antispasmodic; explosives

Phosphoric acid
Library

Phosphoric acid

Triprotic acid; food additive; biochemistry

Phthalic acid
Library

Phthalic acid

Plasticizer feedstock

Phthalic anhydride
Library

Phthalic anhydride

Plasticizer + dye precursor

Piperazine
Library

Piperazine

Saturated 1,4-diazine; pharmacophore

Piperidine
Library

Piperidine

Saturated 6-ring; pharmacophore

Piperine
Library

Piperine

Black pepper alkaloid

Polypropylene (repeat)
Library

Polypropylene (repeat)

PP; common consumer plastic

Polystyrene (repeat)
Library

Polystyrene (repeat)

PS; foam + packaging

Potassium cyanide
Library

Potassium cyanide

Cytochrome c oxidase inhibitor; rapid systemic poison; cyanide salt form

Proline
Library

Proline

Cyclic; helix breaker

Propane
Library

Propane

LPG fuel; bottled gas

Propene
Library

Propene

Polypropylene monomer; Markovnikov demo

Propionaldehyde
Library

Propionaldehyde

C3 aldehyde; plastic precursor

Propionic acid
Library

Propionic acid

Preservative; mold inhibitor

Propylene glycol
Library

Propylene glycol

Food humectant; e-cig vapor base

Propylene oxide
Library

Propylene oxide

Chiral epoxide; polyether monomer

Propyne
Library

Propyne

Methylacetylene; terminal alkyne

Prostaglandin E2
Library

Prostaglandin E2

Inflammation + labor lipid mediator

Pteridine
Library

Pteridine

Folic acid + butterfly pigment core

PTFE (repeat)
Library

PTFE (repeat)

Teflon; non-stick coating

Purine
Library

Purine

Adenine/guanine core

PVC (repeat)
Library

PVC (repeat)

PVC; pipes + flooring

Pyrazine
Library

Pyrazine

1,4-diazine; flavor compound (popcorn)

Pyrazole
Library

Pyrazole

1,2-diazole; drug scaffold

Pyridazine
Library

Pyridazine

1,2-diazine

Pyridine
Library

Pyridine

6-ring aromatic N; weak base; common solvent

Pyridine (basic)
Library

Pyridine (basic)

Weakly basic aromatic N; common base solvent

Pyridoxine (B6)
Library

Pyridoxine (B6)

PLP cofactor for transamination

Pyrimidine
Library

Pyrimidine

1,3-diazine; cytosine/thymine/uracil core

Pyrogallol
Library

Pyrogallol

1,2,3-trihydroxybenzene; oxygen absorber

Pyrrole
Library

Pyrrole

5-ring aromatic NH; porphyrin building block

Quercetin
Library

Quercetin

Flavonoid antioxidant

Quinoline
Library

Quinoline

Fused N-heterocycle; quinine scaffold

Quinoxaline
Library

Quinoxaline

Anticancer scaffold

Raffinose
Library

Raffinose

Trisaccharide; legume gas culprit

Ranitidine
Library

Ranitidine

H2 receptor antagonist

Resorcinol
Library

Resorcinol

1,3-dihydroxybenzene; sunscreen ingredient

Retinal
Library

Retinal

Rhodopsin chromophore

Riboflavin (B2)
Library

Riboflavin (B2)

FAD/FMN precursor

Salicylic acid
Library

Salicylic acid

Aspirin precursor; acne treatment

sec-Butanol
Library

sec-Butanol

Secondary alcohol; ketone source

Selenocysteine
Library

Selenocysteine

21st AA; UGA recoded codon

Serine
Library

Serine

Polar OH; catalytic triad

Simvastatin
Library

Simvastatin

Statin lactone prodrug

SN2 trigonal bipyramidal transition state
Lecture 01

SN2 trigonal bipyramidal transition state

Geometric apex of Walden inversion. 3 H equatorial, Br/I axial along ±z.

Sodium chloride
Library

Sodium chloride

Table salt; biological electrolyte

Sodium hydroxide
Library

Sodium hydroxide

Strong base; saponification; soap making

Sorbitol
Library

Sorbitol

Sugar alcohol; humectant

Sphingosine
Library

Sphingosine

Sphingolipid backbone

Squalane
Library

Squalane

Hydrogenated squalene; cosmetic emollient

Squalene
Library

Squalene

Sterol biosynthesis intermediate

Stearic acid
Library

Stearic acid

C18:0 saturated; tallow

Stigmasterol
Library

Stigmasterol

Plant sterol; cholesterol-lowering

Strychnine
Library

Strychnine

Strychnos seed; glycine antagonist

Styrene
Library

Styrene

Polystyrene monomer

Succinic acid
Library

Succinic acid

TCA cycle intermediate

Succinic anhydride
Library

Succinic anhydride

Acylation reagent

Sucrose
Library

Sucrose

Table sugar; glucose-fructose disaccharide

Sulfur dioxide
Library

Sulfur dioxide

Pollutant; preservative; bleaching agent

Sulfuric acid
Library

Sulfuric acid

Strongest common mineral acid; dehydrating agent

Sulfuryl chloride
Library

Sulfuryl chloride

Chlorinating agent

Tartaric acid
Library

Tartaric acid

Wine acid; Pasteur's chirality discovery

Taurine
Library

Taurine

Sulfonic-acid analog; bile/energy drink

Terephthalic acid
Library

Terephthalic acid

PET polyester monomer

tert-Butanol
Library

tert-Butanol

Tertiary alcohol; high freezing point

tert-Butyl cation
Library

tert-Butyl cation

Stabilized 3° carbocation; SN1/E1 intermediate

tert-Butyl chloride
Library

tert-Butyl chloride

Tertiary; SN1 textbook substrate

Tetracycline
Library

Tetracycline

Broad-spectrum protein synthesis inhibitor

Tetrafluoroethylene
Library

Tetrafluoroethylene

PTFE monomer

Tetrahydrofuran
Library

Tetrahydrofuran

THF; common Grignard solvent

Tetrakis(triphenylphosphine)palladium(0)
Library

Tetrakis(triphenylphosphine)palladium(0)

Cross-coupling Pd(0) catalyst

Tetrazole
Library

Tetrazole

Bioisostere of carboxylic acid

Theophylline
Library

Theophylline

Bronchodilator; PDE inhibitor

Thiazole
Library

Thiazole

S+N 5-ring; vitamin B1 core

Thiazoline
Library

Thiazoline

Penicillin precursor structural unit

Thionyl chloride
Library

Thionyl chloride

OH→Cl conversion; acyl chloride prep

Thiophene
Library

Thiophene

5-ring aromatic S-heterocycle; conducting polymer backbone

Threonine
Library

Threonine

Polar OH; phosphorylation site

Thymine
Library

Thymine

DNA pyrimidine; pairs with A

Thymol
Library

Thymol

Thyme essential oil; antiseptic

Toluene
Library

Toluene

Methylbenzene; solvent; TNT precursor

trans-2-Butene
Library

trans-2-Butene

trans isomer; more stable than cis

trans-Decalin
Library

trans-Decalin

Locked diequatorial chair-chair

Trehalose
Library

Trehalose

Stress-protective sugar

Triethylamine
Library

Triethylamine

Non-nucleophilic base; common in coupling

Trifluoromethane (fluoroform)
Library

Trifluoromethane (fluoroform)

Greenhouse gas; refrigerant byproduct

Triiodothyronine (T3)
Library

Triiodothyronine (T3)

Active thyroid hormone

Trimethylamine
Library

Trimethylamine

Tertiary amine; fish odor

Triphenylmethane
Library

Triphenylmethane

Trityl cation precursor; dye scaffold

Triptycene
Library

Triptycene

D3h rigid 3D scaffold

Tryptophan
Library

Tryptophan

Indole side chain; serotonin precursor

Tyrosine
Library

Tyrosine

Phenolic; thyroid/dopamine precursor

Uracil
Library

Uracil

RNA pyrimidine; pairs with A

Valeric acid
Library

Valeric acid

Pentanoic acid; valerian root

Valine
Library

Valine

Branched-chain essential AA

Vinyl acetate
Library

Vinyl acetate

PVA polymer precursor

Vinyl chloride
Library

Vinyl chloride

PVC monomer; carcinogen

Vinyl fluoride
Library

Vinyl fluoride

Fluoropolymer monomer

Water
Library

Water

Universal solvent; product of combustion/neutralization

Wilkinson's catalyst
Library

Wilkinson's catalyst

Homogeneous alkene hydrogenation

Xanthine
Library

Xanthine

Purine catabolism intermediate

Xylitol
Library

Xylitol

Sugar alcohol; sugar-free sweetener

Yohimbine
Library

Yohimbine

α2-adrenergic antagonist

α-Linolenic acid (ALA)
Library

α-Linolenic acid (ALA)

C18:3 ω-3; flax seed

α-Pinene
Library

α-Pinene

Pine resin monoterpene

α-Tocopherol (E)
Library

α-Tocopherol (E)

Lipid-soluble antioxidant

β-Caryophyllene
Library

β-Caryophyllene

Cannabis sesquiterpene; CB2 agonist

β-Pinene
Library

β-Pinene

Pine + nutmeg essential oil