Stigmast-4-ene-3-one

  • GreenMolBD CID : 126
  • Molecular Formula : C29H48O
  • Molecular Weight : 412.702
  • Exact Molecular Mass : 412.371
  • IUPAC Name : (8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
  • InChI : InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1
  • InChI Key : RUVUHIUYGJBLGI-XJZKHKOHSA-N
  • Canonical SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(C)C
  • Isomeric SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

1.3. Alternative Parent

Triterpenoids; 3-oxo delta-4-steroids; Delta-4-steroids; Cyclohexenones; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; Stigmastane-skeleton; Oxosteroid; 3-oxosteroid; 3-oxo-delta-4-steroid; Delta-4-steroid; Cyclohexenone; Cyclic ketone; Ketone; Organic oxygen compound; Organic oxide; Hydrocarbon derivative; Organooxygen compound; Carbonyl group; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
8.233 17.07 0 1 30 6 0 0 12.7217 662.035 449.428 0.623384

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-219.731323 3.68 -5.062 -10.12029 -0.00288 5.059

4. Compound Reactivity

DLP nRFG nLMR
4 0 2

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 2.57346 22140.9 0.00548738 Moderate Weak None Degradable 1.89E-6 0.101663

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
Stigmast-4-en-3-one
Sitostenone
1058-61-3
4-Stigmasten-3-one
CHEBI:68105
RUVUHIUYGJBLGI-XJZKHKOHSA-N
BETA-ROSASTEROL
NSC 49082
Stigmast-4-en-3-one (8CI)(9CI)
24-Eceo
4-stigmasta-ene-3-one
AC1NUNC2
.DELTA.4-Sitosterol-3-one
CHEMBL66926
SCHEMBL873360
3-oxo-24-ethyl-cholest-4-ene
CTK0H9235
Stigmast-4-en-3-one, (24xi)-
ZINC4073977
AKOS028108888
24(R)-Stigmast-7,22 (E)-dien-3a-ol
(8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
(8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Stigmast-4-ene-3-one

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Stigmast-4-ene-3-one
Abelmoschus esculentus (L.) Moench 5
Areca catechu L. Fruit 9 , 2 , 12
Rhinacanthus communis Leaf; Stem 1
Ricinus communis Aerial 4 , 30

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
320550418AKos Consulting & SolutionsSource URLSource DetailAKOS028108888Source Record URL
321932185AcadechemSource URLSource DetailACDS-060617Source Record URL
342415073Wubei-BiochemSource URLSource DetailWB058518SUSource Record URL
252408646MolepediaSource URLSource DetailM90025881PSource Record URL
274951434ChemFacesSource URLSource DetailCFN99073Source Record URL
57364003NovoSeekSource URLSource Detail5484202Source Record URL
162475275ChemTikSource URLSource DetailCTK0H9235Source Record URL
348530546Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0048697Source Record URL
257129689ZINCSource URLSource DetailZINC4073977Source Record URL
113992325ABI ChemSource URLSource DetailAC1NUNC2Source Record URL
254759381Boc SciencesSource URLSource Detail1058-61-3Source Record URL