ChemFOnt: Showing chemical card for 3beta-Hydroxypregna-5,16-dien-20-one (CFc000282543)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:00 UTC

Chemfont ID

CFc000282543

Molecule Identification

Common Name

3beta-Hydroxypregna-5,16-dien-20-one

Definition

3beta-hydroxypregna-5,16-dien-20-one, also known as 16-dehydropregnenolone or 5,16-pregnadien-3beta-ol-20-one, is a member of the class of compounds known as 20-oxosteroids. 20-oxosteroids are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton. Thus, 3beta-hydroxypregna-5,16-dien-20-one is considered to be a steroid lipid molecule. 3beta-hydroxypregna-5,16-dien-20-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3beta-hydroxypregna-5,16-dien-20-one can be found in fenugreek, which makes 3beta-hydroxypregna-5,16-dien-20-one a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta)-3-Hydroxypregna-5,16-dien-20-one	ChEBI
16-Dehydropregnenolone	ChEBI
5,16-Pregnadien-3beta-ol-20-one	ChEBI
Delta(16)-Pregnenolone	ChEBI
(3b)-3-Hydroxypregna-5,16-dien-20-one	Generator
(3Β)-3-hydroxypregna-5,16-dien-20-one	Generator
5,16-Pregnadien-3b-ol-20-one	Generator
5,16-Pregnadien-3β-ol-20-one	Generator
Δ(16)-pregnenolone	Generator
3b-Hydroxypregna-5,16-dien-20-one	Generator
3Β-hydroxypregna-5,16-dien-20-one	Generator

Chemical Formula

C₂₁H₃₀O₂

Average Molecular Weight

314.469

Monoisotopic Molecular Weight

314.224580206

IUPAC Name

1-[(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-14-yl]ethan-1-one

Traditional Name

16-dehydropregnenolone

CAS Registry Number

1162-53-4

SMILES

[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@]([H])(O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,6,15-16,18-19,23H,5,7-12H2,1-3H3/t15-,16-,18-,19-,20-,21+/m0/s1

InChI Key

YLFRRPUBVUAHSR-RRPFGEQOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

20-oxosteroids

Alternative Parents

Substituents

20-oxosteroid
Androgen-skeleton
Androstane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Ketone
Secondary alcohol
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:27486 )
enone (CHEBI:27486 )
20-oxo steroid (CHEBI:27486 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030164 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303027)

Food

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	4.32	ALOGPS
logP	3.43	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	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	1	ChemAxon
Refractivity	94.63 m³·mol⁻¹	ChemAxon
Polarizability	37.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303027

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007344

KNApSAcK ID

Not Available

Chemspider ID

83836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27486

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3beta-Hydroxypregna-5,16-dien-20-one (CFc000282543)

MOL for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

3D MOL for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

3D SDF for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

3D-SDF for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

PDB for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

3D PDB for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

SMILES for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

INCHI for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

Structure for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)

3D Structure for CFc000282543 (3beta-Hydroxypregna-5,16-dien-20-one)