Stigmast-5-ene-3beta,7alpha-diol

  • GreenMolBD CID : 121
  • Molecular Formula : C29H50O2
  • Molecular Weight : 430.717
  • Exact Molecular Mass : 430.381
  • IUPAC Name : (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
  • InChI : InChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-27,30-31H,7-16H2,1-6H3/t19-,20-,22+,23-,24+,25+,26-,27+,28+,29-/m1/s1
  • InChI Key : SXJVFYZNUGGHRG-GDDJFQTCSA-N
  • Canonical SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C)C(C)C
  • Isomeric SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)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; C24-propyl sterols and derivatives; 7-hydroxysteroids; 3-beta-hydroxysteroids; 3-beta-hydroxy delta-5-steroids; Delta-5-steroids; Secondary alcohols; Cyclic alcohols and derivatives; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

C24-propyl-sterol-skeleton; Stigmastane-skeleton; Triterpenoid; 3-hydroxy-delta-5-steroid; 3-hydroxysteroid; Hydroxysteroid; 7-hydroxysteroid; 3-beta-hydroxy-delta-5-steroid; 3-beta-hydroxysteroid; Delta-5-steroid; Cyclic alcohol; Secondary alcohol; Alcohol; Organooxygen compound; Hydrocarbon derivative; Organic oxygen compound; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
6.9956 40.46 2 2 31 6 0 0 12.9607 677.901 464.694 0.635369

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-271.204017 2.84 -4.442 -9.74562 0.86085 5.303

4. Compound Reactivity

DLP nRFG nLMR
2 0 3

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 2.58318 8197.98 0.00337218 Mild Weak None Degradable 1.43E-5 0.260655

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
34427-61-7
Hydroxysitosterol
Ikshusterol
stigmast-5-ene-3beta,7alpha-diol
(3beta,7alpha)-stigmast-5-ene-3,7-diol
7alpha-Hydroxysitosterol
AC1L4Q4W
SCHEMBL6360492
CHEBI:67594
MolPort-035-706-291
ZINC5925649
Stigmast-5-ene-3,7-diol,(3b,7a)-
PL008742
W2344
Stigmast-5-ene-3,7-diol, (3beta,7alpha)-
(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R,5R)-5-ETHYL-6-METHYLHEPTAN-2-YL]-2,15-DIMETHYLTETRACYCLO[8.7.0.0(2),?.0(1)(1),(1)?]HEPTADEC-7-ENE-5,9-DIOL
(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Stigmast-5-ene-3beta,7alpha-diol
Abelmoschus esculentus (L.) Moench 5

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
274951369ChemFacesSource URLSource DetailCFN98452Source Record URL
252420163MolepediaSource URLSource DetailM90223848PSource Record URL
3565473431717 CheMall CorporationSource URLSource DetailBG01421189Source Record URL
257875953ZINCSource URLSource DetailZINC5925649Source Record URL
103849835AAA ChemistrySource URLSource DetailAR-1L5638Source Record URL
103849836AAA ChemistrySource URLSource DetailAR-1L5639Source Record URL
318505234CambridgeChemSource URLSource DetailCB30572Source Record URL
252551452AK Scientific, Inc. (AKSCI)Source URLSource DetailW2344Source Record URL
113447969ABI ChemSource URLSource DetailAC1L4Q4WSource Record URL
313232090MolPortSource URLSource DetailMolPort-035-706-291Source Record URL
346552497LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN03256013Source Record URL
348991178Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0509324Source Record URL