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tryptophan

AlkaPlorer ID: AK004190

Synonym: 'TRYPTOPHAN', 'alpha-Amino-beta-(3-indolyl)-propionic acid', 'alpha-amino-beta-3-indolepropionic acid', '(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid', 'beta-3-indolylalanine', 'Tryptophan', 'triptofano', 'Htrp', 'L-tryptophan', '(S)-alpha-Amino-beta-(3-indolyl)-propionic acid', '(S)-tryptophan', 'Trp', 'L-Trp', 'W', 'L-Tryptophan', 'tryptophane', '2-amino-3-(1H-indol-3-yl)propanoic acid', 'L-beta-3-indolylalanine', 'L-(-)-tryptophan', '(S)-alpha-amino-1H-indole-3-propanoic acid'

IUPAC Name: (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid

Structure

SMILES: N[C@H](CC1=CNC2=CC=CC=C12)C(=O)O

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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-/m1/s1

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InChIKey: QIVBCDIJIAJPQS-SECBINFHSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Persicaria orientalis Persicaria Polygonaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ginkgo biloba Ginkgo Ginkgoaceae Ginkgoales Ginkgoopsida Streptophyta Viridiplantae Eukaryota
Hedysarum polybotrys Hedysarum Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sinapis alba Sinapis Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Perilla frutescens Perilla Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Calvatia gigantea Calvatia Lycoperdaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Allium chinense Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Brassica juncea Brassica Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium macrostemon Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nelumbo nucifera Nelumbo Nelumbonaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Glycine max Glycine Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium sativum Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Calvatia fenzlii Calvatia Lycoperdaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Calvatia lilacina Calvatia Lycoperdaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Humulus lupulus Humulus Cannabaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pinellia ternata Pinellia Araceae Alismatales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 204.229

TPSA？: 79.11

MolLogP？: 1.1223000000000003

Number of H-Donors: 3

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Burkholderia pseudomallei (strain K96243) 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Kd 1000000.0 nM 10.1016/j.bmcl.2021.128273
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Carbonic anhydrase KA 43.0 uM 10.1016/j.bmc.2009.12.058
Candida glabrata CBS 138 Carbonic anhydrase Ka 12.1 uM 10.1016/j.bmcl.2010.01.054
Cryptococcus neoformans var. grubii Carbonic anhydrase 2 KA 42.1 uM 10.1016/j.bmc.2009.12.058
Homo sapiens Carbonic anhydrase I Ka 41.0 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase I Ka 41.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase I Ka 41.0 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmc.2018.07.011
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmcl.2006.05.023
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmcl.2012.12.009
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.bmcl.2016.11.027
Homo sapiens Carbonic anhydrase I KA 41.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase I Kcat 2.3 10'5/s 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase II Ka 0.37 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase II Ka 12.0 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase II Ka 12.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase II Ka 12.0 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase II Ka 12.0 uM 10.1016/j.bmcl.2009.01.105
Homo sapiens Carbonic anhydrase II Ka 12.0 uM 10.1016/j.bmcl.2010.01.054
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmc.2018.07.011
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmcl.2006.05.023
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmcl.2012.12.009
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.bmcl.2016.11.027
Homo sapiens Carbonic anhydrase II KA 12.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase II Kcat 6.1 10'5/s 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase III Ka 19.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase III Ka 19.0 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase III KA 19.0 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase III KA 19.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase IV Ka 39.6 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase IV Ka 40.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase IV KA 39.6 uM 10.1016/j.bmcl.2009.05.026
Homo sapiens Carbonic anhydrase IV KA 40.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase IX Ka 43.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase IX KA 43.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase IX KA 43.6 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase VA Ka 1.24 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase VA KA 1.2 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VA KA 1.24 uM 10.1016/j.bmcl.2006.11.075
Homo sapiens Carbonic anhydrase VB Ka 1.35 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase VB KA 1.3 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VB KA 1.35 uM 10.1016/j.bmcl.2006.11.075
Homo sapiens Carbonic anhydrase VI Ka 39.0 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase VI Ka 39.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase VI KA 39.0 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase VI KA 39.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VI Kcat 4.8 10'5/s 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase VII Ka 39.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase VII KA 39.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VII KA 39.6 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase XII Ka 28.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase XII KA 28.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase XII KA 28.1 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase XIII KA 0.81 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase XIV Ka 18.0 uM 10.1016/j.bmc.2008.08.043
Homo sapiens Carbonic anhydrase XIV KA 18.0 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase XIV KA 18.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Dihydrofolate reductase Ki 880000.0 nM 10.1021/acs.jmedchem.0c00546
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 44668.4 nM None
Homo sapiens Geminin Potency 33498.3 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 19952.6 nM None
Homo sapiens Histone deacetylase 6 Inhibition -8.19 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 12.03 % 10.6019/CHEMBL4808148
Homo sapiens Huntingtin Potency 31622.8 nM None
Homo sapiens L-type amino acid transporter 1 Activity 81.0 % 10.1021/acs.jmedchem.8b01007
Homo sapiens L-type amino acid transporter 1 IC50 380000.0 nM 10.1021/acs.jmedchem.8b01007
Homo sapiens L-type amino acid transporter 1 Inhibition 29.0 % 10.1021/acs.jmedchem.8b01007
Homo sapiens Matrix metalloproteinase 3 IC50 500000.0 nM 10.1021/jm00027a027
Homo sapiens Prelamin-A/C Potency 89.1 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 21192.3 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 39810.7 nM None
Homo sapiens T1R1/T1R3 Activity nan None None
Methanobacterium thermoautotrophicum Carbonic anhydrase Ka 41.0 uM 10.1016/j.bmcl.2010.01.054
Methanosarcina thermophila Carbonic anhydrase KA 33.0 uM 10.1016/j.bmcl.2016.11.027
Mus musculus Carbonic anhydrase 15 KA 8.7 uM 10.1016/j.bmcl.2009.05.026
Mus musculus Carbonic anhydrase XIII Ka 0.81 uM 10.1016/j.bmc.2008.08.043
Mus musculus Carbonic anhydrase XIII KA 0.81 uM 10.1016/j.bmcl.2006.05.023
Plasmodium falciparum Plasmodium falciparum Potency 1510.1 nM None
Rattus norvegicus Monocarboxylate transporter 10 Activity nan None 10.1074/jbc.m009462200
Rattus norvegicus Peripheral myelin protein 22 Potency 28695.4 nM None
Saccharomyces cerevisiae S288c Carbonic anhydrase Ka 90.0 uM 10.1016/j.bmcl.2009.01.105
Saccharomyces cerevisiae S288c Carbonic anhydrase Ka 90.0 uM 10.1016/j.bmcl.2010.01.054
Trypanosoma brucei 6-phospho-1-fructokinase Potency 11220.2 nM None
Trypanosoma cruzi (strain CL Brener) Carbonic anhydrase-like protein, putative KA 1.79 uM 10.1016/j.bmc.2018.07.011
None No relevant target LogD7.4 -0.92 None 10.6019/CHEMBL3301361
None Unchecked Ac50 0.7943 uM None
None Unchecked Ac50 7.943 uM None
None Unchecked Ac50 39.81 uM None
None Unchecked AC50 794.3 nM None
None Unchecked AC50 7943.3 nM None
None Unchecked AC50 39810.7 nM None
None Unchecked Ka 41.0 uM 10.1016/j.bmcl.2009.01.105
None Unchecked KA 0.002 uM 10.1016/j.bmcl.2012.08.088
None Unchecked KA 0.002 uM 10.1016/j.bmcl.2012.12.009
None Unchecked KA 0.003 uM 10.1016/j.bmcl.2012.12.009
None Unchecked KA 0.052 uM 10.1016/j.bmcl.2016.11.027
None Unchecked KA 6.18 uM 10.1016/j.bmc.2018.07.011
None Unchecked KA 12.5 uM 10.1016/j.bmcl.2016.01.078
None Unchecked KA 19.0 uM 10.1016/j.bmc.2010.01.059
None Unchecked KA 33.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked KA 41.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked KA 68.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked Kcat 2.44 10'6/s 10.1016/j.bmcl.2016.11.027
None Unchecked Kcat 6.4 10'5/s 10.1016/j.bmc.2010.01.059
None Unchecked Potency 19952.6 nM None
None Unchecked Potency 35481.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000872 *OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)[C@H](N)Cc2c[nH]c3ccccc23)[C@@H]1O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O MNXR185003
AKRT002146 CC(=O)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>C[C@@H](N)C(=O)O.O=C(O)C(=O)Cc1c[nH]c2ccccc12 None
AKRT002147 CC(=O)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccccc12 enzymemap_41843
AKRT003091 CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>CC(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O None
AKRT003092 CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O D-TRYPTOPHAN-N-ACETYLTRANSFERASE-RXN
AKRT004713 CC(=O)[CoA].N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O D-TRYPTOPHAN-N-ACETYLTRANSFERASE-RXN
AKRT005250 CC(C)=CCOP(=O)(O)OP(=O)(O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>CC(C)=CCc1cccc2[nH]cc(C[C@@H](N)C(=O)O)c12 enzymemap_40443
AKRT005251 CC(C)=CCOP(=O)(O)OP(=O)(O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>CC(C)=CCc1cccc2c(C[C@@H](N)C(=O)O)c[nH]c12 enzymemap_41294
AKRT007196 CCC(=O)[CoA].N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>CCC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_30748
AKRT010975 CO.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>COC(=O)[C@H](N)Cc1c[nH]c2ccccc12 enzymemap_52989
AKRT011126 COC(=O)[C@H](N)Cc1c[nH]c2ccccc12>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_52989
AKRT012722 C[C@@H](N)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_67347
AKRT014690 C[SAH].N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>Cc1[nH]c2ccccc2c1C[C@@H](N)C(=O)O enzymemap_25746
AKRT017130 NC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_77867
AKRT019801 N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O 60516
AKRT020286 N[C@H](CO)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_83450
AKRT020330 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_90704
AKRT020331 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.O=C(O)CC(=O)[CoA]>>O=C(O)CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O D-TRYPTOPHAN-N-MALONYLTRANSFERASE-RXN
AKRT020332 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>C[C@@H](N)C(=O)O enzymemap_41843
AKRT020333 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N=C(O)[C@H](N)Cc1c[nH]c2ccccc12 MNXR131570
AKRT020334 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>NC(CC(=O)c1ccccc1NC=O)C(=O)O RXN-8664
AKRT020335 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@@H](CC(=O)c1ccccc1NC=O)C(=O)O MNXR177273
AKRT020336 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O None
AKRT020337 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](CC(=O)c1ccccc1NC=O)C(=O)O enzymemap_9655
AKRT020338 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@H](Cc1c[nH]c2cc(Cl)ccc12)C(=O)O RXN-19634
AKRT020339 N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccccc12 MNXR130695
AKRT022588 O=C(O)C(=O)Cc1c[nH]c2ccccc12>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O retrobiocat_360
AKRT022713 O=C(O)CC(=O)[CoA].N[C@H](Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)CC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_28475