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Tryptophan-cholic acid

CAT: 0804-HY-N15721-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N15721-01Size:5 mg
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Description
Tryptophan-cholic acid (Trp-CA) is a microbial amino-acid-conjugated bile acid, serving as an endogenous ligand and agonist of the orphan G protein-coupled receptor (GPCR) MRGPRE. Tryptophan-cholic acid activates MRGPRE, promoting the secretion of glucagon-like peptide-1 (GLP-1) through the Gs-cAMP and β-arrestin-1-ALDOA signaling pathways, thereby improving glucose tolerance in diabetic mice. Tryptophan-cholic acid is promising for research of type 2 diabetes[1].
CAS Number
1630745-39-9
Product Name Alternative
Trp-CA
UNSPSC
12352005
Target
Orphan GPCR
Related Pathways
GPCR/G Protein
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease
Concentration
10mM
Purity
99.75
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@H]1[C@@]2([H])[C@@]3([H])[C@@]([C@@](CC3)([H])[C@H](C)CCC(N[C@H](C(O)=O)CC4=CNC5=CC=CC=C45)=O)([C@H](C[C@]2([H])[C@@]6([C@](C[C@@H](CC6)O)([H])C1)C)O)C
Molecular Formula
C35H50N2O6
Molecular Weight
594.78
References & Citations
[1]Lin J, et al. A microbial amino-acid-conjugated bile acid, tryptophan-cholic acid, improves glucose homeostasis via the orphan receptor MRGPRE. Cell. 2025 May 22:S0092-8674 (25) 00560-4.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Tryptophan-cholic acid

Cholyl-L-tryptophan is a 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. It is a secondary carboxamide, a monocarboxylic acid, a bile acid conjugate, a 3alpha-hydroxy steroid, a 7alpha-hydroxy steroid, a 12alpha-hydroxy steroid and a L-tryptophan derivative. It is functionally related to a cholic acid and a L-tryptophan. It is a conjugate acid of a cholyl-L-tryptophan(1-).

CAS Number1630745-39-9
PubChem CID101584917
IUPAC Name(2S)-3-(1H-indol-3-yl)-2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propanoic acid
Molecular FormulaC35H50N2O6
Molecular Weight594.8
XLogP5
Topological Polar Surface Area143
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Heavy Atom Count43
Formal Charge0
Complexity1040
SMILES
C[C@H](CCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O)[C@H]3CC[C@@H]4[C@@]3([C@H](C[C@H]5[C@H]4[C@@H](C[C@H]6[C@@]5(CC[C@H](C6)O)C)O)O)C
InChI
InChI=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
InChIKey
UXWZMQPNSYWAHX-DMELVVMMSA-N
Chemical Structure
2D Structure
2D structure of Tryptophan-cholic acid
CAS: 1630745-39-9
CID: 101584917
Formula: C35H50N2O6
MW: 594.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight594.8
XLogP35
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass594.36688732
Monoisotopic Mass594.36688732
Topological Polar Surface Area143 Ų
Heavy Atom Count43
Formal Charge0
Complexity1040
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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