TRP

TRYPTOPHAN

Created:	1999-07-08
Last modified:	2023-11-03

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220 entries where TRP is found as a standalone ligand15 entries where TRP is covalently linked to polymer or other heterogen groups 199,436 entries where TRP is found in a polymer sequence

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Chemical Details
Formal Charge	0
Atom Count	27
Chiral Atom Count	1
Bond Count	28
Aromatic Bond Count	10

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Chemical Component Summary
Name	TRYPTOPHAN
Systematic Name (OpenEye OEToolkits)	(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Formula	C₁₁ H₁₂ N₂ O₂
Molecular Weight	204.225
Type	L-PEPTIDE LINKING

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(N)Cc2c1ccccc1nc2
SMILES	CACTVS	3.341	N[CH](Cc1c[nH]c2ccccc12)C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	c1ccc2c(c1)c(c[nH]2)CC(C(=O)O)N
Canonical SMILES	CACTVS	3.341	N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)O)N
InChI	InChI	1.03	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
InChIKey	InChI	1.03	QIVBCDIJIAJPQS-VIFPVBQESA-N

Drug Info: DrugBank

DrugBank ID	DB00150
Name	Tryptophan
Groups	approved withdrawn nutraceutical
Description	An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals.
Synonyms	Tryptophan L-Tryptophan Trp Tryptophanum (S)-α-amino-1H-indole-3-propanoic acid Tryptophane (S)-alpha-Amino-beta-(3-indolyl)-propionic acid (S)-Tryptophan L-β-3-indolylalanine W L-(−)-tryptophan (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid L-(-)-Tryptophan Triptofano
Brand Names	Smofkabiven Peripheral 2.75% Travas. Amino Acid InJ.W.elecw.25%dex 8.5% Freamine III Aminosyn RF Injection 4.25% Travasol Amino Acid Injection Without Electrolytes In 25% Dextrose Tryptan Aminosyn II Olimel 3.3% E Aminosyn II with Electrolytes in Dextrose with Calcium Vamin N Aminosyn 8.5% Injection With Electrolytes Clinimix Aminosyn Nutrineal Pd4 4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose Quickmix Aminosyn II 7% With 50% Dextrose Primene 10% Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose Injec Travasol Amino Acid Inj 8.5% Aminosyn II 7% M In 10% Dextrose(dual Chamber) Smofkabiven Electrolyte Free 4.25% Travasol Amino Acid Injection Without Electrlytes In 10% Dextrose 4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose Olimel 7.6% 4.25%trav. Amino Acid InJ.W.O.elect.5%dext. HepatAmine 2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose Quickmix Aminosyn II 8.5% With 50% Dextrose PMS-tryptophan Aminosyn II and Dextrose Plenamine 5% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose Injec 2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose Perikabiven 4.25% Travasol Amino Acid Injection Without Electrolytes In 20% Dextrose Dom-tryptophan Aminosyn HF Aminosyn II In Dextrose Injection Aminosyn 3.5% M Aminosyn II 8.5% M In 20% Dextrose (dual Chamber) 4.25% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose Aminosyn II 8.5% Injection Primene 10%-liq IV Teva-tryptophan Clinimix E Clinisol 2.75%travasol Amino Acid InJ.W.eleC.W.5%dex. RenAmin 2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose Clinimix Olimel 5.7% 2.5%travasol Amino Acid InJ.W.eleC.W.25%dex Olimel 7.6% E 4.25% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose Travasol E 4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose Quickmix Vamin 18 Electrolyte-free NephrAmine Aminosyn-PF Olimel 5.7% E Premasol - sulfite-free (Amino Acid) 2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose Quickmix Aminosyn 10% W Electrolytes PHL-tryptophan Aminosyn Sulfite Free 4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose Quickmix Aminosyn RF Aminosyn-PF 10% Aminosyn II in Dextrose Primene Novamine Aminosyn 5% Aminosyn 8.5% Periolimel 2.5% E Travasol Inj Without Electrolytes 8.5% Travasol Inj Without Electrolytes 5.5% Nephramine Liq IV Travasol Amino Acid Inj 5.5% 4.25%travasol Amino Acid InJ.W.elecw.5%dex. Travasol Apo-tryptophan Renamin (amino Acids) Injection Smofkabiven Synthamin Olimel 4.4% 5% Travasol Amino Acid Injection Without Electrolytes In 25% Dextrose ProSol 4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose Quickmix Hepatasol Aminosyn-PF 7% ProcalAmine TrophAmine Aminosyn II 7% With 10% Dextrose Smofkabiven Extra Nitrogen Electrolyte Free FreAmine HBC Aminosyn II 5% Inj FreAmine III Aminosyn II 10% With Electrolytes 2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose Quickmix Smofkabiven Extra Nitrogen 20% Prosol Aminosyn II with Electrolytes Essepna Olimel 4.4% E 5% Travasol Amino Acid Injection Without Electrolytes In 20% Dextrose Aminosyn II 7% Injection Aminosyn 7% Kabiven
Indication	Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
Categories	Amino Acids Amino Acids, Aromatic Amino Acids, Cyclic Amino Acids, Essential Amino Acids, Peptides, and Proteins Antidepressive Agents Antidepressive Agents, Second-Generation Central Nervous System Agents Central Nervous System Depressants Dietary Supplements Miscellaneous Antidepressants Nervous System Proteinogenic Amino Acids Psychoanaleptics Psychotropic Drugs Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Supplements
ATC-Code	N06AX02
CAS number	73-22-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tryptophan--tRNA ligase, cytoplasmic	MPNSEPASLLELFNSIATQGELVRSLKAGNASKDEIDSAVKMLVSLKMSY...	unknown	inhibitor
Tryptophan--tRNA ligase	MKTIFSGIQPSGVITIGNYIGALRQFVELQHEYNCYFCIVDQHAITVWQD...	unknown	inhibitor
Tryptophan--tRNA ligase, mitochondrial	MALHSMRKARERWSFIRALHKGSAAAPALQKDSKKRVFSGIQPTGILHLG...	unknown	inhibitor
Tryptophan--tRNA ligase	MKTIFSGIQPSGVITIGNYIGALRQFVELQHEYNCYFCIVDQHAITVWQD...	unknown	substrate,inhibitor
Tryptophan--tRNA ligase, mitochondrial	MALHSMRKARERWSFIRALHKGSAAAPALQKDSKKRVFSGIQPTGILHLG...	unknown	substrate,inhibitor
Tryptophan 5-hydroxylase 1	MIEDNKENKDHSLERGRASLIFSLKNEVGGLIKALKIFQEKHVNLLHIES...	unknown	substrate
Tryptophan 5-hydroxylase 2	MQPAMMMFSSKYWARRGFSLDSAVPEEHQLLGSSTLNKPNSGKNDDKGNK...	unknown	substrate
Tryptophan--tRNA ligase, cytoplasmic	MPNSEPASLLELFNSIATQGELVRSLKAGNASKDEIDSAVKMLVSLKMSY...	unknown	substrate,inhibitor
Indoleamine 2,3-dioxygenase 1	MAHAMENSWTISKEYHIDEEVGFALPNPQENLPDFYNDWMFIAKHLPDLI...	unknown	substrate
Tryptophan 2,3-dioxygenase	MSGCPFLGNNFGYTFKKLPVEGSEEDKSQTGVNRASKGGLIYGNYLHLEK...	unknown	substrate
Aromatic-L-amino-acid decarboxylase	MNASEFRRRGKEMVDYMANYMEGIEGRQVYPDVEPGYLRPLIPAAAPQEP...	unknown	substrate
Monocarboxylate transporter 8	MALQSQASEEAKGPWQEADQEQQEPVGSPEPESEPEPEPEPEPVPVPPPE...	unknown	inhibitor
Monocarboxylate transporter 10	MVLSQEEPDSARGTSEAQPLGPAPTGAAPPPGPGPSDSPEAAVEKVEVEL...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource Name	Reference
PubChem	6305, 6923516
ChEMBL	CHEMBL54976
ChEBI	CHEBI:57912, CHEBI:16828
CCDC/CSD	TAJSUV, QQQBTP02, RODSOU, IMENAR, TAKKAU, TRYPTB, TRYPTF10, XAMCEW, BEBCAP, TPTPCM, TRYPTC, HUKDEZ, HUKDID, KELKAO01, TRYPTC02, TRYPTD11, PUKBEE, KELKAO, GOSWOC, QQQBTP05, TAKJOH, BEBCET, PUKFAE, TAKJUN, CEBPUV, NUYDOB, HAGBOG, ZAKPOU