ChemFOnt: Showing chemical card for 5a-Cholestane-3a,7a,12a,23,25-pentol (CFc000000434)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:49 UTC

Chemfont ID

CFc000000434

Molecule Identification

Common Name

5a-Cholestane-3a,7a,12a,23,25-pentol

Definition

5a-Cholestane-3a,7a,12a,23,25-pentol is a bile acid found in the urine of patients with cerebrotendinous xanthomatosis. (PMID 1805458 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3a,5a,7a,12a,23S)-Cholestane-3,7,12,23,25-pentol	HMDB

Chemical Formula

C₂₇H₄₈O₅

Average Molecular Weight

452.667

Monoisotopic Molecular Weight

452.350174646

IUPAC Name

(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

CAS Registry Number

137252-15-4

SMILES

[H][C@@]12CC[C@H]([C@@H](C)CC(O)CC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17+,18?,19+,20-,21-,22+,23-,24-,26-,27+/m0/s1

InChI Key

OXSBBBPDYVCAKC-KHMINMIBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Pentahydroxy bile acid, alcohol, or derivatives
Cholestane-skeleton
25-hydroxysteroid
23-hydroxysteroid
3-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31643938)
Bile (PMID: 31643938)

Excreta

Biofluid or Excreta

Feces (PMID: 31643938)
Urine (PMID: 1112456)

Organ

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000558)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000558)

Source

Endogenous

Endogenous (HMDB: HMDB0000558)

Animal

Animal (HMDB: HMDB0000558)

Exogenous

Food

Food (HMDB: HMDB0000558)

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: HMDB0000558)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000558)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000558)

Lipid metabolism pathway (HMDB: HMDB0000558)

Cellular process

Cell signaling (HMDB: HMDB0000558)

Biochemical process

Lipid transport (HMDB: HMDB0000558)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	2.33	ALOGPS
logP	2.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.93	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.34 m³·mol⁻¹	ChemAxon
Polarizability	53.69 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	No	ChemAxon

External Links

HMDB ID

HMDB0000558

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022118

KNApSAcK ID

Not Available

Chemspider ID

13628108

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5542

PubChem Compound

21252254

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5a-Cholestane-3a,7a,12a,23,25-pentol (CFc000000434)

MOL for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

3D MOL for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

3D SDF for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

3D-SDF for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

PDB for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

3D PDB for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

SMILES for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

INCHI for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

Structure for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)

3D Structure for CFc000000434 (5a-Cholestane-3a,7a,12a,23,25-pentol)