Showing Compound N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine (FDB023035)

Record Information

Version

1.0

Creation date

2011-09-21 00:23:37 UTC

Update date

2015-07-21 06:57:29 UTC

Primary ID

FDB023035

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine

Description

N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is an acyl glycine and a sulfated 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). As a bile acid sulfate, N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is typically found in urine. These conjugates are formed as a part of detoxification of endogenous and exogenous components in the body (PMID:3584362). [HMDB]

CAS Number

71977-73-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulphooxy)cholan-24-yl]-glycine	Generator
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetic acid	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	0.059	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.58 m³·mol⁻¹	ChemAxon
Polarizability	58.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C26H43NO9S

IUPAC name

2-[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

InChI Identifier

InChI=1S/C26H43NO9S/c1-14(4-7-22(30)27-13-23(31)32)17-5-6-18-24-19(12-21(29)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)36-37(33,34)35/h14-21,24,28-29H,4-13H2,1-3H3,(H,27,30)(H,31,32)(H,33,34,35)/t14-,15+,16-,17-,18?,19?,20-,21+,24?,25+,26-/m1/s1

InChI Key

BJPPZTDOLXZUSK-NLKBZSSJSA-N

Isomeric SMILES

[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@@H](C2)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O

Average Molecular Weight

545.686

Monoisotopic Molecular Weight

545.265852669

Classification

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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Sulfate-ester
Sulfuric acid monoester
Fatty acyl
Fatty amide
Sulfuric acid ester
Alkyl sulfate
N-acyl-amine
Cyclic alcohol
Organic sulfuric acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Organ and components:

Source:

Biological:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gl9-1231490000-253283480a4fc4a47a7b	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2110129000-a9dfafcc5584b8686baf	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, "N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-2000490000-2e8d2cfb1348e6d760d3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-6000920000-cca4d584b697cef683eb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9002400000-b0343d0969f16bb3a4f6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0000290000-f5afc42d6a3480129a02	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-3000930000-f62f0db1db3c100bce9d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9101100000-fbc092ad5516e9401161	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-fee96f51477bba0d1d44	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-2000290000-1a2b57c158397d0e4193	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000320000-8a28de6f794a57ce1524	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0000090000-6b6a2f9cd994ee7fd4bb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fv-6413490000-b5b0edeb8a2748d05391	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9301100000-bfb0977d7351d65bda46	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

13628378

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

21252317

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02640

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Glycine N-acyltransferase	GLYAT	Q6IB77
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Glycine N-acyltransferase-like protein 2	GLYATL2	Q8WU03
Glycine N-acyltransferase-like protein 3	GLYATL3	Q5SZD4