Tryptophan

Details

• Internal ID: 0d251f89-fef2-44b4-b9fe-5dd20aac7c35
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
• InChI Key: QIVBCDIJIAJPQS-VIFPVBQESA-N
• Popularity: 94,899 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22 g/mol
• Exact Mass: 204.089877630 g/mol
• Topological Polar Surface Area (TPSA): 79.10 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 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-beta-3-Indolylalanine
• L-Tryptofan
• L-Trp
• L-(-)-Tryptophan
• 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]
• (S)-alpha-Amino-1H-indole-3-propanoic acid
• (L)-TRYPTOPHAN
• alpha'-Amino-3-indolepropionic acid
• L-alpha-amino-3-indolepropionic acid
• L-alpha-Aminoindole-3-propionic acid
• (S)-alpha-Aminoindole-3-propionic acid
• EH 121
• Alanine, 3-indol-3-yl-
• Trytophan-
• L-Alanine, 3-(1H-indol-3-yl)-
• 1H-Indole-3-alanine, (S)-
• NCI-C01729
• (S)-alpha-amino-beta-(3-indolyl)-propionic acid
• AI3-18478
• Indole-3-propionic acid, alpha-amino-
• CHEBI:16828
• Propionic acid, 2-amino-3-indol-3-yl-
• 1H-Indole-3-propanoic acid, alpha-amino-, (S)-
• Tryptophan ((-),l,s)
• 8DUH1N11BX
• NSC 13119
• DTXSID5021419
• (S)-alpha-Amino-beta-indolepropionic acid
• alpha-Amino-beta-(3-indolyl)-propionic acid
• NSC-13119
• DTXCID801419
• alpha-Aminoindole-3-propionic acid
• Tryptophanum (Latin)
• (2S)-2-amino-3-(1H-indol-3-yl)propanoate
• 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
• CHEBI:27897
• L-TTP
• h-Trp-oh
• Kalma
• L(-)-Tryptophan
• Tryptophan (VAN)
• Tryptophan (H-3)
• Triptofano [Spanish]
• Lyphan
• Tryptan
• Tryptophane [French]
• Tryptophan [USAN:INN]
• Sedanoct
• trp
• 1H-Indole-3-alanine (VAN)
• (S)-2-Amino-3-(3-indolyl)propionic acid
• CCRIS 617
• MFCD00064340
• alpha-Amino-3-indolepropionic acid, L-
• HSDB 4142
• Lopac-T-0254
• CHEMBL54976
• M02943
• l-b-3-Indolylalanine
• CAS-73-22-3
• Propionic acid, 2-amino-3-indol-3-yl
• L-Tryptophan (9CI)
• (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
• 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
• 1qaw
• 80206-30-0
• 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
• L-TRYPTOPHAN [USP-RS]
• (s)-a-amino-b-indolepropionate
• orb1297181
• orb1310615
• 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]
• 202406-50-6
• HY-N0623
• STR02722
• (S)-alpha-Aminoindole-3-propionate
• Tox21_201246
• Tox21_300359
• Tox21_501183
• 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
• 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
• T0541
• (S)-Tryptophan 1H-Indole-3-alanine, (S)-
• EN300-52634
• 73T223
• C00078
• D00020
• L-.ALPHA.-AMINO-3-INDOLEPROPIONIC ACID
• L-Tryptophan, reagent grade, >=98% (HPLC)
• P16427
• 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
• L-Tryptophan, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	-	0.5406	54.06%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Lysosomes	0.3925	39.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9654	96.54%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6827	68.27%
P-glycoprotein inhibitior	-	0.9918	99.18%
P-glycoprotein substrate	-	0.9387	93.87%
CYP3A4 substrate	-	0.6384	63.84%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.6970	69.70%
CYP3A4 inhibition	-	0.9432	94.32%
CYP2C9 inhibition	-	0.9481	94.81%
CYP2C19 inhibition	-	0.9644	96.44%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.9531	95.31%
CYP2C8 inhibition	-	0.8219	82.19%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.7121	71.21%
Eye corrosion	-	0.9964	99.64%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.8721	87.21%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7086	70.86%
Micronuclear	+	0.7774	77.74%
Hepatotoxicity	+	0.5166	51.66%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9051	90.51%
Acute Oral Toxicity (c)	IV	0.6272	62.72%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.7630	76.30%
Thyroid receptor binding	-	0.7898	78.98%
Glucocorticoid receptor binding	-	0.5889	58.89%
Aromatase binding	-	0.6975	69.75%
PPAR gamma	-	0.4871	48.71%
Honey bee toxicity	-	0.9523	95.23%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8549	85.49%
Fish aquatic toxicity	-	0.7169	71.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	89.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.42%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.38%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	92.62%	90.20%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.17%	94.62%
CHEMBL2581	P07339	Cathepsin D	90.92%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	90.35%	83.82%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	87.74%	83.10%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.77%	88.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.97%	89.62%
CHEMBL221	P23219	Cyclooxygenase-1	81.12%	90.17%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.81%	95.56%

Plants that contains it

• Allium chinense
• Allium sativum
• Amaranthus spinosus
• Ananas comosus
• Antirrhinum majus
• Apium graveolens
• Arabidopsis thaliana
• Artemisia absinthium
• Artemisia armeniaca
• Atractylodes lancea
• Beta vulgaris
• Bupleurum chinense
• Cannabis sativa
• Castanea sativa
• Cynomorium coccineum subsp. songaricum
• Equisetum ramosissimum var. huegelii
• Fragaria × ananassa
• Fragaria chiloensis
• Geranium pratense
• Glycine max
• Hordeum vulgare
• Hydrilla verticillata
• Linum usitatissimum
• Lobelia nummularia
• Lupinus albus
• Marchantia polymorpha
• Mimosa pudica
• Moringa oleifera
• Neltuma juliflora
• Onobrychis viciifolia
• Opuntia ficus-indica
• Panax notoginseng
• Peucedanum japonicum
• Pinus ponderosa
• Piper kadsura
• Populus tremula
• Prunus domestica
• Ripariosida hermaphrodita
• Smallanthus sonchifolius
• Stratiotes aloides
• Tabernaemontana divaricata
• Tecoma stans
• Telekia speciosa
• Treculia africana
• Ulmus thomasii
• Vaccinium dunalianum
• Vitis vinifera
• Youngia japonica
• Zea mays

Cross-Links

• PubChem: 6305
• NPASS: NPC203468
• ChEMBL: CHEMBL54976
• LOTUS: LTS0263809
• wikiData: Q181003