ChemFOnt: Showing chemical card for 5-beta-pregnan-3,20 dione (CFc000283737)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:17 UTC

Chemfont ID

CFc000283737

Molecule Identification

Common Name

5-beta-pregnan-3,20 dione

Definition

(5beta)-pregnane-3,20-dione, also known as 3,20-pregnanedione or 5beta-dihydroprogesterone, belongs to gluco/mineralocorticoids, progestogins and derivatives class of compounds. Those are steroids with a structure based on a hydroxylated prostane moiety. Thus, (5beta)-pregnane-3,20-dione is considered to be a steroid lipid molecule (5beta)-pregnane-3,20-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5beta)-pregnane-3,20-dione can be found in a number of food items such as opium poppy, walnut, rowal, and italian sweet red pepper, which makes (5beta)-pregnane-3,20-dione a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5BETA)-PREGNANE-3,20-dione	ChEBI
3,20-Pregnanedione	ChEBI
5beta-Dihydroprogesterone	ChEBI
5beta-Pregnan-3,20-dione	ChEBI
(5b)-PREGNANE-3,20-dione	Generator
(5Β)-pregnane-3,20-dione	Generator
5b-Dihydroprogesterone	Generator
5Β-dihydroprogesterone	Generator
5b-Pregnan-3,20-dione	Generator
5Β-pregnan-3,20-dione	Generator
5-b-Pregnan-3,20 dione	Generator
5-Β-pregnan-3,20 dione	Generator

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

(1S,2S,7R,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

(5β)-pregnane-3,20-dione

CAS Registry Number

128-23-4

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O

InChI Identifier

InChI=1S/C21H32O2/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/h14,16-19H,4-12H2,1-3H3/t14-,16+,17-,18+,19+,20+,21-/m1/s1

InChI Key

XMRPGKVKISIQBV-XWOJZHJZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-5-beta-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:30154 )
20-oxo steroid (CHEBI:30154 )
C21-steroid (CHEBI:30154 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030146 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0013 g/L	ALOGPS
logP	4.06	ALOGPS
logP	4.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.34	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.88 m³·mol⁻¹	ChemAxon
Polarizability	37.74 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