ChemFOnt: Showing chemical card for 3beta-Hydroxy-5-cholestenoic acid (CFc000007978)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:34 UTC

Chemfont ID

CFc000007978

Molecule Identification

Common Name

3beta-Hydroxy-5-cholestenoic acid

Definition

3beta-Hydroxy-5-cholestenoic acid (CAS: 6561-58-6) belongs to the class of organic compounds known as monohydroxy bile acids, alcohols, and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 3beta-Hydroxy-5-cholestenoic acid is found in the primary bile acid biosynthesis pathway. 3beta-Hydroxy-5-cholestenoic acid is created from cholest-5-ene-3 beta,26-diol through the action of CYP27A (EC 1.14.13.15). 3beta-Hydroxy-5-cholestenoic acid is then converted into 3beta,7alpha-dihydroxy-5-cholestenoic acid by the action of CYP7B (EC 1.14.13.100). 3beta-Hydroxy-5-cholestenoic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphoserine	HMDB
Phosphatidylserine(16:1/18:1)	HMDB
Phosphatidylserine(16:1n7/18:1n9)	HMDB
Phosphatidylserine(16:1W7/18:1W9)	HMDB
Phosphatidylserine(34:2)	HMDB
PS(16:1/18:1)	HMDB
PS(16:1N7/18:1N9)	HMDB
PS(16:1W7/18:1W9)	HMDB
PS(34:2)	HMDB
pSer(16:1/18:1)	HMDB
pSer(16:1n7/18:1n9)	HMDB
pSer(16:1W7/18:1W9)	HMDB
pSer(34:2)	HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoserine	HMDB
(3beta)-3-Hydroxy-cholest-5-en-26-Oate	HMDB
(3beta)-3-Hydroxy-cholest-5-en-26-Oic acid	HMDB
3 beta-Hydroxycholest-5-en-27-Oate	HMDB
3 beta-Hydroxycholest-5-en-27-Oic acid	HMDB
3-HCOA	HMDB, MeSH
3-Hydroxy-5-cholesten-26-Oate	HMDB
3-Hydroxy-5-cholesten-26-Oic acid	HMDB, MeSH
3-Hydroxy-5-cholestenoate	HMDB
3-Hydroxy-5-cholestenoic acid	HMDB, MeSH
3beta-Hydroxy-5-cholesten-26-Oate	HMDB
3beta-Hydroxy-5-cholesten-26-Oic acid	HMDB
3beta-Hydroxy-5-cholestenoate	HMDB
3beta-Hydroxy-5-cholestenoic acid	HMDB
3 b-Hydroxy-5-cholestenoate	Generator
3 b-Hydroxy-5-cholestenoic acid	Generator
3 beta-Hydroxy-5-cholestenoic acid	Generator
3 Β-hydroxy-5-cholestenoate	Generator
3 Β-hydroxy-5-cholestenoic acid	Generator
3-Hydroxy-5-cholestenoic acid, (3beta,25S)-isomer	MeSH
3-Hydroxy-5-cholestenoic acid, 26-14(C)-labeled	MeSH
3-Hydroxycholest-5-en-26-Oic acid	MeSH
3 beta-Hydroxy-5-cholesten-26-Oic acid	MeSH
3-Hydroxy-5-cholestenoic acid, (3beta,25R)-isomer	MeSH

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

Traditional Name

(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

CAS Registry Number

56845-87-5

SMILES

C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18?,20+,21?,22?,23?,24?,26+,27-/m1/s1

InChI Key

WVXOMPRLWLXFAP-UBJAGWMESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010901 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31477923)

Cellular substructure

Extracellular (HMDB: HMDB0012453)
Membrane (HMDB: HMDB0012453)

Source

Endogenous

Endogenous (HMDB: HMDB0012453)

Exogenous

Exogenous (HMDB: HMDB0012453)

Food

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0012453)

Disease pathway

Congenital Bile Acid Synthesis Defect Type III (HMDB: HMDB0012453)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	5.57	ALOGPS
logP	6.05	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.31 m³·mol⁻¹	ChemAxon
Polarizability	50.2 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

External Links

HMDB ID

HMDB0012368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028986

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

52926009

PDB ID

Not Available

ChEBI ID

90032

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3beta-Hydroxy-5-cholestenoic acid (CFc000007978)

MOL for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

3D MOL for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

3D SDF for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

3D-SDF for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

PDB for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

3D PDB for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

SMILES for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

INCHI for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

Structure for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)

3D Structure for CFc000007978 (3beta-Hydroxy-5-cholestenoic acid)