ChemFOnt: Showing chemical card for Cholylaspartic acid (CFc000222631)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:43:36 UTC

Chemfont ID

CFc000222631

Molecule Identification

Common Name

Cholylaspartic acid

Definition

Cholylaspartic acid belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Cholylaspartic acid consists of the bile acid cholic acid conjugated to the amino acid Aspartic acid conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070 ). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Cholylaspartic acid, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176 ) or microbially conjugated bile acids (MCBAs) (PMID: 34127070 ). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176 ). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176 ). Cholylaspartic acid appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176 ). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070 ). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[(1-Hydroxy-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}pentylidene)amino]butanedioate	Generator
Cholylaspartate	Generator
Asp-Cho	HMDB
Asp-CA	HMDB
Aspartocholic acid	HMDB
Aspartocholate	HMDB

Chemical Formula

C₂₈H₄₅NO₈

Average Molecular Weight

523.667

Monoisotopic Molecular Weight

523.314517413

IUPAC Name

2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanedioic acid

Traditional Name

2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanedioic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(=O)NC(CC(O)=O)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C

InChI Identifier

InChI=1S/C28H45NO8/c1-14(4-7-23(33)29-20(26(36)37)13-24(34)35)17-5-6-18-25-19(12-22(32)28(17,18)3)27(2)9-8-16(30)10-15(27)11-21(25)31/h14-22,25,30-32H,4-13H2,1-3H3,(H,29,33)(H,34,35)(H,36,37)

InChI Key

VMFFESMCXOCOIZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
7-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
3-hydroxysteroid
Aspartic acid or derivatives
Acyl-homoserine
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.39 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.12 m³·mol⁻¹	ChemAxon
Polarizability	57.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0242381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cholylaspartic acid (CFc000222631)

MOL for CFc000222631 (Cholylaspartic acid)

3D MOL for CFc000222631 (Cholylaspartic acid)

3D SDF for CFc000222631 (Cholylaspartic acid)

3D-SDF for CFc000222631 (Cholylaspartic acid)

PDB for CFc000222631 (Cholylaspartic acid)

3D PDB for CFc000222631 (Cholylaspartic acid)

SMILES for CFc000222631 (Cholylaspartic acid)

INCHI for CFc000222631 (Cholylaspartic acid)

Structure for CFc000222631 (Cholylaspartic acid)

3D Structure for CFc000222631 (Cholylaspartic acid)