Stigmasta-4,22-dien-3-one

  • GreenMolBD CID : 111
  • Molecular Formula : C29H46O
  • Molecular Weight : 410.686
  • Exact Molecular Mass : 410.355
  • IUPAC Name : (8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-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/C29H46O/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/h8-9,18-21,24-27H,7,10-17H2,1-6H3/b9-8+/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1
  • InChI Key : MKGZDUKUQPPHFM-LPJPOILFSA-N
  • Canonical SMILES : CCC(C=CC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(C)C
  • Isomeric SMILES : CCC(/C=C/C(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
8.009 17.07 0 1 30 5 0 0 12.7123 656.133 448.004 0.625919

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-185.034861 3.55 -4.952 -9.90449 0.00088 4.953

4. Compound Reactivity

DLP nRFG nLMR
4 0 4

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 2.28323 19797.4 0.00343221 Moderate Weak Mild Degradable 3.56E-6 0.0958911

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
Stigmasta-4,22-dien-3-one
20817-72-5
55722-32-2
4,22-Stigmastadien-3-one
4,22-Cholestadien-24-ethyl-3-one
(22E)-Stigmasta-4,22-dien-3-one
AC1O5WRB
CHEMBL3138641
MKGZDUKUQPPHFM-LPJPOILFSA-N
MolPort-023-298-999
(8S,9S,10R,13R,14S,17R)-17-((E,2S,5S)-5-Ethyl-6-methyl-hept-3-en-2-yl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one
24-Ethyl-4,22E-cholestadien-3-one
AKOS022184742
ZINC118912442
(22E)-Stigmasta-4,22-diene-3-one
4,22-Cholestadien-24beta-ethyl-3-one
4,22-Cholestadien-24-beta-ethyl-3-one
AJ-82229
AK104349
PL050172
W2338
(1S,2R,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ETHYL-6-METHYLHEPT-3-EN-2-YL]-2,15-DIMETHYLTETRACYCLO[8.7.0.0(2),?.0(1)(1),(1)?]HEPTADEC-6-EN-5-ONE
(1S,2R,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-5-one
(1S,2R,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
(8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Stigmasta-4,22-dien-3-one
Abelmoschus esculentus (L.) Moench 4

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
274951571ChemFacesSource URLSource DetailCFN98934Source Record URL
252076706Bide Pharmatech Ltd.Source URLSource DetailBD235888Source Record URL
215784145AKos Consulting & SolutionsSource URLSource DetailAKOS022184742Source Record URL
223591400A&J Pharmtech CO., LTD.Source URLSource DetailAJ-82229Source Record URL
252422926MolepediaSource URLSource DetailM90284254PSource Record URL
189628272MolPortSource URLSource DetailMolPort-023-298-999Source Record URL
162190426AK Scientific, Inc. (AKSCI)Source URLSource DetailW2338Source Record URL
347787301Alfa ChemistrySource URLSource Detail20817-72-5Source Record URL
271100117ZINCSource URLSource DetailZINC118912442Source Record URL
162088748Chembase.cnSource URLSource Detail102761Source Record URL
250213175Founder PharmaSource URLSource DetailFD29058Source Record URL
252338516AHH Chemical co.,ltdSource URLSource DetailMT-40413Source Record URL
347238493LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01301789Source Record URL
3565243631717 CheMall CorporationSource URLSource DetailBG01398209Source Record URL
114565274ABI ChemSource URLSource DetailAC1O5WRBSource Record URL