ContaminantDB: N-[(3a,5b,7a)-3-Hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine

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

Record Information

Version

1.0

Creation Date

2016-05-26 05:46:31 UTC

Update Date

2016-11-09 01:21:19 UTC

Accession Number

CHEM035447

Identification

Common Name

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

Class

Small Molecule

Description

N-[(3a,5b,7a)-3-hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine (Glycochenodeoxycholate 7-sulfate) is an acyl glycine and a bile acid-glycine conjugate. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Glycochenodeoxycholate 7-sulfate is also a sulphated bile acid. Sulphated bile acids are found mainly in the urine. The sulphate group not only prevents its tubular reabsorption but also its absorption from the intestine.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
N-(3alpha-Hydroxy-7alpha-sulfooxy-5beta-cholan-24-oyl)glycine	ChEBI
N-(3a-Hydroxy-7a-sulfooxy-5b-cholan-24-oyl)glycine	Generator
N-(3a-Hydroxy-7a-sulphooxy-5b-cholan-24-oyl)glycine	Generator
N-(3alpha-Hydroxy-7alpha-sulphooxy-5beta-cholan-24-oyl)glycine	Generator
N-(3Α-hydroxy-7α-sulfooxy-5β-cholan-24-oyl)glycine	Generator
N-(3Α-hydroxy-7α-sulphooxy-5β-cholan-24-oyl)glycine	Generator
N-[(3a,5b,7a)-3-Hydroxy-24-oxo-7-(sulphooxy)cholan-24-yl]-glycine	Generator
Glycochenodeoxycholate 7-sulfate	HMDB, Generator
Glycochenodeoxycholate 7-sulphate	HMDB, Generator
Glycochenodeoxycholic acid 7-sulfate	HMDB
Glycochenodeoxycholic acid 7-sulphate	HMDB
Glycochenodeoxycholyl 7-sulfate	HMDB
Glycochenodeoxycholyl 7-sulphate	HMDB
Glycochenodeoxycholic acid 7-sulfuric acid	Generator, HMDB
Glycochenodeoxycholic acid 7-sulphuric acid	Generator, HMDB

Chemical Formula

C₂₆H₄₃NO₈S

Average Molecular Mass

529.687 g/mol

Monoisotopic Mass

529.271 g/mol

CAS Registry Number

67030-55-1

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

SMILES

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

InChI Identifier

InChI=1S/C26H43NO8S/c1-15(4-7-22(29)27-14-23(30)31)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)35-36(32,33)34/h15-21,24,28H,4-14H2,1-3H3,(H,27,29)(H,30,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sulfooxy steroid (CHEBI:52031 )
Glycine conjugates (LMST05030005 )

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
Water Solubility	0.012 g/L	ALOGPS
logP	0.01	ALOGPS
logP	1.44	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.23 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.07 m³·mol⁻¹	ChemAxon
Polarizability	57.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	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	splash10-0nt9-1211950000-240f1393275d0bac60f0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-2101029000-bba999add02a63a5ade4	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_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 (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("N-[(3a,5b,7a)-3-hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-4000890000-ce4f58a5852e63ef500d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-8002900000-45211dfeaddffb7ceabe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9004200000-f6a2ab7ebcea4fd6a951	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000490000-677a58b1c1864daa52b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008a-3000920000-f2cab07a2ae7567da387	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9101100000-02088e18627c221a62ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-47108d59914be103681d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-4000980000-f0f78192720fd9ab5ea6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-9000220000-835a84594b88cd9fdeb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0001490000-9c8c9ba0b4d069fd40a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1004910000-731d52c3c088f18e6273	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-9341400000-a24f7508c4b762026cb0	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002496

FooDB ID

FDB023014

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Lepage G, Roy CC, Weber AM. Separation of sulfated from non-sulfated serum bile acids without the use of Sephadex columns. J Lipid Res. 1981 May;22(4):705-11.

N-[(3a,5b,7a)-3-Hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine (CHEM035447)

Structure for CHEM035447: N-[(3a,5b,7a)-3-Hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine