ChemFOnt: Showing chemical card for 5alpha-cholesta-8,24-dien-3-one (CFc000283738)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:18 UTC

Chemfont ID

CFc000283738

Molecule Identification

Common Name

5alpha-cholesta-8,24-dien-3-one

Definition

5alpha-cholesta-8,24-dien-3-one, also known as zymosterone, belongs to cholesterols and derivatives class of compounds. Those are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholesta-8,24-dien-3-one is considered to be a sterol lipid molecule. 5alpha-cholesta-8,24-dien-3-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 5alpha-cholesta-8,24-dien-3-one can be found in a number of food items such as cloudberry, welsh onion, oil-seed camellia, and loquat, which makes 5alpha-cholesta-8,24-dien-3-one a potential biomarker for the consumption of these food products. 5alpha-cholesta-8,24-dien-3-one may be a unique S.cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Zymosterone	ChEBI

Chemical Formula

C₂₇H₄₂O

Average Molecular Weight

382.6218

Monoisotopic Molecular Weight

382.323565966

IUPAC Name

(2S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

Traditional Name

5α-cholesta-8,24-dien-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20+,23-,24+,26+,27-/m1/s1

InChI Key

AUNLIRXIJAVBNM-ZSBATXSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:52386 )
Cholesterol and derivatives (LMST01010168 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00071 g/L	ALOGPS
logP	6.92	ALOGPS
logP	6.87	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.17 m³·mol⁻¹	ChemAxon
Polarizability	48.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030588

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

22298942

PDB ID

Not Available

ChEBI ID

52386

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5alpha-cholesta-8,24-dien-3-one (CFc000283738)

MOL for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

3D MOL for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

3D SDF for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

3D-SDF for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

PDB for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

3D PDB for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

SMILES for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

INCHI for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

Structure for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)

3D Structure for CFc000283738 (5alpha-cholesta-8,24-dien-3-one)