ChemFOnt: Showing chemical card for 3a,7b,12a-Trihydroxyoxocholanyl-Glycine (CFc000000234)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:34 UTC

Chemfont ID

CFc000000234

Molecule Identification

Common Name

3a,7b,12a-Trihydroxyoxocholanyl-Glycine

Definition

3a,7b,12a-Trihydroxyoxocholanyl-Glycine is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). 3a,7b,12a-Trihydroxyoxocholanyl-Glycine is a specific ketonic bile acid found in the urine of infants during the neonatal period. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha,7beta,12alpha-Trihydroxyoxocholanyl-glycine	HMDB
Glycocholic acid	HMDB
N-Cholylglycine	HMDB

Chemical Formula

C₂₆H₄₃NO₆

Average Molecular Weight

465.6227

Monoisotopic Molecular Weight

465.309038113

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

68753-51-5

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20+,21+,24+,25+,26-/m1/s1

InChI Key

RFDAIACWWDREDC-IFZPJRIXSA-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
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Cyclic alcohol
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Alcohol
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Glycine conjugates (LMST05030007 )

Functional Ontology

Not Available

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000331)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000331)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000331)

Source

Endogenous

Endogenous (HMDB: HMDB0000331)

Animal

Animal (HMDB: HMDB0000331)

Exogenous

Food

Food (HMDB: HMDB0000331)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000331)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000331)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000331)

Lipid metabolism pathway (HMDB: HMDB0000331)

Cellular process

Cell signaling (HMDB: HMDB0000331)

Biochemical process

Lipid transport (HMDB: HMDB0000331)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000331)

Molecular messenger

Signaling molecule (HMDB: HMDB0000331)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000331)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.38	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.59 m³·mol⁻¹	ChemAxon
Polarizability	52.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000331

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021956

KNApSAcK ID

Not Available

Chemspider ID

24850145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44263376

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dayal, B.; Rapole, K. R.; Salen, G.; Shefer, S.; Tint, G. S.; Wilson, S. R. Microwave-induced rapid synthesis of bile acid conjugates. Synlett (1995), (8), 861-2.

Showing chemical card for 3a,7b,12a-Trihydroxyoxocholanyl-Glycine (CFc000000234)

MOL for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

3D MOL for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

3D SDF for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

3D-SDF for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

PDB for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

3D PDB for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

SMILES for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

INCHI for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

Structure for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)

3D Structure for CFc000000234 (3a,7b,12a-Trihydroxyoxocholanyl-Glycine)