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CHEBI:232263 - cholyl-L-tryptophan

ChEBI IDCHEBI:232263
ChEBI Namecholyl-L-tryptophan
Stars
ASCII Namecholyl-L-tryptophan
DefinitionA bile acid conjugate resulting from the formal condensation of the carboxy group of cholic acid with the amino group of L-tryptophan. It improves glucose tolerance in diabetic mice.
Secondary ChEBI IDsCHEBI:182917, CHEBI:231078
Last Modified17 June 2025
SubmitterMetaboLights, Michael Witting
DownloadsMolfile
FormulaC35H50N2O6
Net Charge0
Average Mass594.793
Monoisotopic Mass594.36689
SMILES[H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]1([H])C[C@H](O)[C@@]3(C)[C@@]([H])(CC[C@]3([H])[C@H](C)CCC(=O)N[C@@H](Cc3cnc4ccccc34)C(=O)O)[C@]1([H])[C@H](O)C2
InChIInChI=1S/C35H50N2O6/c1-19(8-11-31(41)37-28(33(42)43)14-20-18-36-27-7-5-4-6-23(20)27)24-9-10-25-32-26(17-30(40)35(24,25)3)34(2)13-12-22(38)15-21(34)16-29(32)39/h4-7,18-19,21-22,24-26,28-30,32,36,38-40H,8-17H2,1-3H3,(H,37,41)(H,42,43)/t19-,21+,22-,24-,25+,26+,28+,29-,30+,32+,34+,35-/m1/s1
InChIKeyUXWZMQPNSYWAHX-DMELVVMMSA-N
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) feces (BTO:0000440) MetaboLights (MTBLS9100)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
cholyl-L-tryptophan (CHEBI:232263) has functional parent L-tryptophan (CHEBI:16828)
cholyl-L-tryptophan (CHEBI:232263) has functional parent cholic acid (CHEBI:16359)
cholyl-L-tryptophan (CHEBI:232263) is a L-tryptophan derivative (CHEBI:47994)
cholyl-L-tryptophan (CHEBI:232263) is a 12α-hydroxy steroid (CHEBI:36846)
cholyl-L-tryptophan (CHEBI:232263) is a 3α-hydroxy steroid (CHEBI:36835)
cholyl-L-tryptophan (CHEBI:232263) is a 7α-hydroxy steroid (CHEBI:36843)
cholyl-L-tryptophan (CHEBI:232263) is a bile acid conjugate (CHEBI:36249)
cholyl-L-tryptophan (CHEBI:232263) is a monocarboxylic acid (CHEBI:25384)
cholyl-L-tryptophan (CHEBI:232263) is a secondary carboxamide (CHEBI:140325)
cholyl-L-tryptophan (CHEBI:232263) is conjugate acid of cholyl-L-tryptophan(1−) (CHEBI:234456)
Incoming Relation(s)
cholyl-L-tryptophan(1−) (CHEBI:234456) is conjugate base of cholyl-L-tryptophan (CHEBI:232263)
IUPAC Name 
(2S)-2-[(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido]-3-(1H-indol-3-yl)propanoic acid
Synonyms  Source
cholyl-tryptophanChEBI
cholyltryptophanChEBI
N-(3α,7α,12α-trihydroxy-5β-cholan-24-oyl)-L-tryptophanChEBI
Nα-(24-oxo-3α,7α,12α-trihydroxy-5β-cholane-24-yl)-L-tryptophanChEBI
L-tryptophan conjugated cholic acidChEBI
L-tryptophan-conjugated cholic acidChEBI
Manual XrefsDatabases
HMDB0242374HMDB
Citations