ChemFOnt: Showing chemical card for (22alpha)-Hydroxy-campest-4-en-3-one (CFc000007672)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:06 UTC

Chemfont ID

CFc000007672

Molecule Identification

Common Name

(22alpha)-Hydroxy-campest-4-en-3-one

Definition

(22alpha)-Hydroxy-campest-4-en-3-one 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. Thus, (22alpha)-hydroxy-campest-4-en-3-one is considered to be a sterol lipid molecule. (22alpha)-Hydroxy-campest-4-en-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (22alpha)-Hydroxy-campest-4-en-3-one is involved in the brassinosteroid biosynthesis pathway. (22alpha)-Hydroxy-campest-4-en-3-one is created from either campest-4-en-3-one or 22alpha-hydroxy-campesterol through the actions of steroid 22-alpha-hydroxylase (EC 1.14.13.-) or Sax1, respectively. (22alpha)-Hydroxy-campest-4-en-3-one is then converted into 22alpha-hydroxy-5alpha-campestan-3-one by steroid reductase DET2 (EC 1.3.99.-).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(22a)-Hydroxy-campest-4-en-3-one	Generator
(22Α)-hydroxy-campest-4-en-3-one	Generator

Chemical Formula

C₂₈H₄₆O₂

Average Molecular Weight

414.6636

Monoisotopic Molecular Weight

414.349780716

IUPAC Name

(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

208586-81-6

SMILES

CC(C)[C@H](C)C[C@H](O)[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C28H46O2/c1-17(2)18(3)15-26(30)19(4)23-9-10-24-22-8-7-20-16-21(29)11-13-27(20,5)25(22)12-14-28(23,24)6/h16-19,22-26,30H,7-15H2,1-6H3/t18-,19+,22?,23?,24?,25?,26+,27+,28-/m1/s1

InChI Key

FMFAICDKESPFNH-HSKWBYRYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Ergostane-skeleton
Monohydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
3-oxosteroid
Hydroxysteroid
3-oxo-delta-4-steroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Ketone
Secondary alcohol
Cyclic ketone
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012113)

Source

Exogenous

Exogenous (HMDB: HMDB0012113)

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)

Endogenous

Endogenous (HMDB: HMDB0012113)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00016 g/L	ALOGPS
logP	5.13	ALOGPS
logP	6.66	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.71 m³·mol⁻¹	ChemAxon
Polarizability	51.61 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

HMDB0012113

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028777

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

25201842

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (22alpha)-Hydroxy-campest-4-en-3-one (CFc000007672)

MOL for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D MOL for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D SDF for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D-SDF for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

PDB for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D PDB for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

SMILES for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

INCHI for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

Structure for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D Structure for CFc000007672 ((22alpha)-Hydroxy-campest-4-en-3-one)