ContaminantDB: GLYCOCHOLIC ACID

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 02:07:26 UTC

Update Date

2016-11-09 01:09:37 UTC

Accession Number

CHEM005872

Identification

Common Name

GLYCOCHOLIC ACID

Class

Small Molecule

Description

Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine	ChEBI
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	ChEBI
N-Choloylglycine	ChEBI
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine	Generator
3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine	Generator
N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	Generator
N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine	Generator
Glycocholate	Generator
Glycine cholate	HMDB
Glycocholic acid, sodium salt	HMDB
Cholylglycine	HMDB
Glycocholate sodium	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine	HMDB
3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide	HMDB
3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine	HMDB
3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide	HMDB
Glycoreductodehydrocholic acid	HMDB
Glycylcholate	HMDB
Glycylcholic acid	HMDB
N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide	HMDB
N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide	HMDB
N-Choloyl-glycine	HMDB
Glycocholic acid	HMDB

Chemical Formula

C₂₆H₄₃NO₆

Average Molecular Mass

465.623 g/mol

Monoisotopic Mass

465.309 g/mol

CAS Registry Number

475-31-0

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

SMILES

[H][C@@](C)(CCC(O)=NCC(O)=O)[C@@]1([H])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

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-FRVQLJSFSA-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
3-alpha-hydroxysteroid
7-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Cyclic alcohol
Secondary alcohol
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboximidic acid
Monocarboxylic acid or derivatives
Carboximidic acid derivative
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

bile acid glycine conjugate (CHEBI:17687 )
C26 bile acids, alcohols, and derivatives (C01921 )
Glycine conjugates (C01921 )
Cholane and derivatives (C01921 )
Glycine conjugates (LMST05030001 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
logP	1.38	ChemAxon
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.14	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	52.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-0000900000-52e93813a9681b93b67c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-03k9-4000900000-79dfcaf6e620e89a8f51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-0153bf31bdc096136252	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000400000-e797c46f8e20c716b24c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000200000-478282fdac3fd2f1d8a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000900000-ea860edeae64135340d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000300000-9a12b83610eacbe64ab6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-54d1a3d9fa6179530909	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000900000-e81f9c948a937824aad7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-7872961e706b0ce2acef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0000900000-d2c234df86de685accab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-3950000000-5e1c0bb11352c04bf6ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1245900000-820e9f5a57e1ee8bcc05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0125900000-2a2d378bef3e5d7d7ef3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03g0-2896300000-3561f6267f9465ea26a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-092i-2896300000-a9ffe90b7ae4ed58097b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-06vi-2950000000-acdd4501d3673c8d4f18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0000900000-6e1ef68f12bc3fcd4183	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0000900000-5010fdb018700f1ff637	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ea-5001900000-32dcdb2995334e0be0c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9001200000-efaede61ec6ea62b8f4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9001000000-4a63863012ce5e7f9e89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0000900000-e906f3d7308d2f341edc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0h2b-2001900000-b325ccc2ef8a18eae690	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9101100000-9cd953b22c5f0740b0bb	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum