Compound: L-tryptophan
SMILES: O=C(O)[C@@H](N)Cc1c2c(cccc2)[nH]c1
InChIKey: QIVBCDIJIAJPQS-VIFPVBQESA-N
Synonyms: L-tryptophan, tryptophan, 73-22-3, L-Tryptophane, Tryptophane, (S)-Tryptophan, trofan, tryptacin, (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid, Ardeytropin, Pacitron, Indole-3-alanine, L-Tryptofan, L-Trp, L-(-)-Tryptophan, L-beta-3-Indolylalanine, 3-Indol-3-ylalanine, triptofano, (-)-Tryptophan, 1-beta-3-Indolylalanine, Tryptophan, L-, 1H-Indole-3-alanine, Tryptophanum, 1beta-3-Indolylalanine, 2-Amino-3-indolylpropanoic acid, Tryptophanum [Latin], (L)-TRYPTOPHAN, (S)-alpha-Amino-1H-indole-3-propanoic acid, alpha'-Amino-3-indolepropionic acid, L-alpha-Aminoindole-3-propionic acid, (S)-alpha-Aminoindole-3-propionic acid, L-alpha-amino-3-indolepropionic acid, EH 121, Alanine, 3-indol-3-yl-, Trytophan-, L-Alanine, 3-(1H-indol-3-yl)-, 1H-Indole-3-alanine, (S)-, NCI-C01729, AI3-18478, Indole-3-propionic acid, alpha-amino-, Propionic acid, 2-amino-3-indol-3-yl-, (S)-alpha-amino-beta-(3-indolyl)-propionic acid, 1H-Indole-3-propanoic acid, alpha-amino-, (S)-, Tryptophan ((-),l,s), 8DUH1N11BX, NSC 13119, DTXSID5021419, CHEBI:16828, (S)-alpha-Amino-beta-indolepropionic acid, NSC-13119, DTXCID801419, alpha-Aminoindole-3-propionic acid, Tryptophanum (Latin), alpha-Amino-beta-(3-indolyl)-propionic acid, (2S)-2-amino-3-(1H-indol-3-yl)propanoate, CHEBI:27897, Levotryptophan, Naturruhe, l-tryptophanum, (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate, l tryptophan, Optimax wv, ratio Tryptophan, ratio-Tryptophan, Gppe pdr sach, PMS Tryptophan, L-Tryptophan High, L-Tryptophan 7423, L Tryptophan ratiopharm, RefChem:6508, L-Tryptophan High 7424, N06AX02, (2S)-2-Amino-3-(indol-3-yl)propanoic acid, (S)-2-Amino-3-(1H-indol-3-yl)-propanoic acid, 200-795-6, L-TTP, h-Trp-oh, Kalma, Tryptan, L(-)-Tryptophan, Tryptophan (VAN), Tryptophan (H-3), Triptofano [Spanish], Lyphan, Tryptophane [French], Tryptophan [USAN:INN], Sedanoct, trp, 1H-Indole-3-alanine (VAN), CCRIS 617, alpha-Amino-3-indolepropionic acid, L-, HSDB 4142, (S)-2-Amino-3-(3-indolyl)propionic acid, Lopac-T-0254, (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid, CHEMBL54976, MFCD00064340, M02943, l-b-3-Indolylalanine, 3-beta-Indolylalanine, CAS-73-22-3, Propionic acid, 2-amino-3-indol-3-yl, L-Tryptophan (9CI), Tryptophan (USP/INN), (S)-a-Amino-b-indolepropionic acid, (S)-a-Aminoindole-3-propionic acid, Alanine, 3-indol-3-yl, EINECS 200-795-6, L-Tryptophan-13C11,15N2, UNII-8DUH1N11BX, trytophan, (S)-a-Amino-1H-indole-3-propanoic acid, TRP-01, L-Trytophan, Tryptophan CRS, 1qaw, 80206-30-0, 202406-50-6, L-Trp-OH, Tryptophan [WHO-DD], 2a4m, TRYPTOPHAN [II], TRYPTOPHAN [MI], L-Tryptophan (JP18), L-Tryptophan (standard), TRYPTOPHAN [INN], S(-)-1-alpha-Aminoindole-3-propionic acid, TRYPTOPHAN [HSDB], TRYPTOPHAN [USAN], Tryptophan (L-Tryptophan), TRYPTOPHAN [VANDF], Tryptophan, L- (8CI), bmse000050, bmse000868, bmse001017, Epitope ID:136043, EC 200-795-6, T 0254, L-TRYPTOPHAN [FCC], L-TRYPTOPHAN [JAN], SCHEMBL7328, TRYPTOPHAN [MART.], 2-Amino-3-indolylpropanoate, (S)-(-)-2-Amino-3-(3-indolyl)propionic Acid, (S)-1H-Indole-3-alanine, Lopac0_001183, GTPL717, L-TRYPTOPHAN [VANDF], MLS001056750, DivK1c_000457, Tryptophan EP Impurity C-D4, L-TRYPTOPHAN [USP-RS], (s)-a-amino-b-indolepropionate, orb1297181, orb1310615, orb3139585, orb3139805, SCHEMBL1119669, 151A3008-4CFE-40C9-AC0B-467EF0CB50EA, SCHEMBL23141133, SCHEMBL28341856, (S)-a-Aminoindole-3-propionate, BDBM21974, HMS501G19, HY-N0623R, KBio1_000457, MSK1418, TRYPTOPHAN [EP MONOGRAPH], 3-(1H-indol-3-yl)-L-Alanine, L-a-Amino-3-indolepropionic acid, NINDS_000457, HMS3263N07, Pharmakon1600-01500600, TRYPTOPHAN [USP MONOGRAPH], HY-N0623, STR02722, (S)-alpha-Aminoindole-3-propionate, Tox21_201246, Tox21_300359, Tox21_501183, EBC-01051, NSC757373, s3987, (s)-alpha-amino-beta-indolepropionate, L-Tryptophan, Vetec(TM), 98.5%, (S)-a-Amino-1H-indole-3-propanoate, AKOS015854052, Indoe-3-propionic acid, alpha-amino-, CCG-205257, CS-W020011, DB00150, ET06029, LP01183, NSC-757373, SDCCGSBI-0051150.P002, IDI1_000457, L-2-Amino-3-(3-indolyl)propionic acid, NCGC00015994-01, NCGC00094437-01, NCGC00094437-02, NCGC00094437-03, NCGC00094437-04, NCGC00094437-08, NCGC00254424-01, NCGC00258798-01, NCGC00261868-01, (S)-alpha-Amino-1H-indole-3-propanoate, AC-17050, BP-13286, IS_TRYPTOPHAN-2,4,5,6,7-D5, SMR000326686, TS-04426, propanoic acid, 2-amino-3-(3-indolyl)-, DB-029986, L-Tryptophan, BioUltra, >=99.5% (NT), EU-0101183, NS00003513, (S)-Tryptophan 1H-Indole-3-alanine, (S)-, EN300-52634, C00078, D00020, L-.ALPHA.-AMINO-3-INDOLEPROPIONIC ACID, L-Tryptophan, reagent grade, >=98% (HPLC), P16427, T-8320, AB00373874_05, L-Tryptophan, Vetec(TM) reagent grade, >=98%, (S)-2-amino-3-(1H-Indol-3-yl)-propionic acid, L-Tryptophan, Cell Culture Reagent (H-L-Trp-OH), Q181003, SR-01000075590, N-ACETYLTRYPTOPHAN IMPURITY A [EP IMPURITY], SR-01000075590-1, BRD-K83776863-001-05-5, BRD-K83776863-001-08-9, F0001-2364, Z756440056, 1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-AMINO-, (S)-, L-Tryptophan, certified reference material, TraceCERT(R), Tryptophan, European Pharmacopoeia (EP) Reference Standard, L-Tryptophan, United States Pharmacopeia (USP) Reference Standard, Tadalafil Impurity O; Tryptophan; N-Acetyltryptophan EP Impurity A, L-Tryptophan, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%
Theoretical properties:
molecular_formula: C11H12N2O2
molecular_weight: 204.22 g/mol
exact_mass: 204.089877630 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 15
topological_polar_surface_area: 79.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Leaflets or plates from dilute alcohol
color: Leaflets or plates from dilute alcohol
odor: Odorless
melting_point: 554 to 558 °F (Decomposes) (NTP, 1992)
solubility: 1 to 5 mg/mL at 68 °F (NTP, 1992)
Descriptions:
pubchem: L-tryptophan is the L-enantiomer of tryptophan. It has a role as a micronutrient, an antidepressant, a nutraceutical, a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite and a human metabolite. It is a L-alpha-amino acid, a tryptophan, an erythrose 4-phosphate/phosphoenolpyruvate family amino acid and a proteinogenic amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion.
chebi: The <small>L</small>-enantiomer of tryptophan.
chembl: TRYPTOPHAN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG.
Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH+3; pKa = 9.39) and the carboxylic acid is deprotonated (–COO−; pKa = 2.38).
Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid.
Tryptophan is named after the digestive enzymes trypsin, which were used in its first isolation from casein proteins. It was assigned the one-letter symbol W based on the double ring being visually suggestive to the bulky letter.