ChemFOnt: Showing chemical card for (1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one (CFc000138575)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:13:51 UTC

Chemfont ID

CFc000138575

Molecule Identification

Common Name

(1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Definition

(8S,9S,10R,13S,14S,17R)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, also known as 4-pregnene-11beta,17alpha-diol-3,20-dione or 11beta,17alpha-dihydroxyprogesterone, 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. Based on a literature review very few articles have been published on (8S,9S,10R,13S,14S,17R)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Pregnene-11beta,17alpha-diol-3,20-dione	Kegg
11beta,17alpha-Dihydroxyprogesterone	Kegg
4-Pregnene-11b,17a-diol-3,20-dione	Generator
4-Pregnene-11β,17α-diol-3,20-dione	Generator
11b,17a-Dihydroxyprogesterone	Generator
11Β,17α-dihydroxyprogesterone	Generator

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.467

Monoisotopic Molecular Weight

346.214409446

IUPAC Name

(1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17?,18+,19-,20-,21-/m0/s1

InChI Key

LCZBQMKVFQNSJR-AVOSZYNGSA-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-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

deoxycortisol (CHEBI:28697 )
Glucocorticoids (C05497 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05497 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.7 m³·mol⁻¹	ChemAxon
Polarizability	38.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0158167

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389584

KEGG Compound ID

C05497

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440709

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one (CFc000138575)

MOL for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

3D MOL for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

3D SDF for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

3D-SDF for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

PDB for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

3D PDB for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

SMILES for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

INCHI for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

Structure for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)

3D Structure for CFc000138575 ((1S,2R,10S,11S,14R,15S)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one)