Stigmast-4-en-3beta,6beta-diol

  • GreenMolBD CID : 123
  • Molecular Formula : C29H50O2
  • Molecular Weight : 430.717
  • Exact Molecular Mass : 430.381
  • IUPAC Name : (3S,6R,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
  • InChI : InChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-25,27,30-31H,7-15,17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,27-,28-,29-/m1/s1
  • InChI Key : OOUCIUZOGLWLAN-NDDUEHJASA-N
  • Canonical SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CC(C4=CC(CCC34C)O)O)C)C(C)C
  • Isomeric SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CC(C4=CC(CCC34C)O)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; 6-hydroxysteroids; 3-hydroxy delta-4-steroids; 3-beta-hydroxysteroids; Delta-4-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-hydroxysteroid; Hydroxysteroid; 6-hydroxysteroid; 3-hydroxy-delta-4-steroid; 3-beta-hydroxysteroid; Delta-4-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
-270.59429 0.98 -4.355 -9.7377 1.02776 5.383

4. Compound Reactivity

DLP nRFG nLMR
3 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 3.96027 8252.15 0.00336522 Mild Weak None Degradable 1.33E-5 0.253791

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
CHEMBL487767
113626-76-9
stigmast-4-ene-3beta,6beta-diol
Stigmast-4-ene-3,6-diol, (3beta,6beta)-
stigmast-4-en-3beta,6beta-diol
MolPort-039-338-103
BDBM50275561
ZINC39013169
AKOS027250669
AJ-97338

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Stigmast-4-en-3beta,6beta-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
154 nitric oxide synthase 2, inducible Nos2 Mus musculus 50 344829
155 Nitric Oxide Synthase, inducible Mus musculus >50000 10.1016/j.bmc.2008.09.021 18926710

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
223606509A&J Pharmtech CO., LTD.Source URLSource DetailAJ-97338Source Record URL
252076579Bide Pharmatech Ltd.Source URLSource DetailBD235750Source Record URL
346552969LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN03258163Source Record URL
318358282CambridgeChemSource URLSource DetailCB31091Source Record URL
261329847ZINCSource URLSource DetailZINC39013169Source Record URL
317806149AKos Consulting & SolutionsSource URLSource DetailAKOS027250669Source Record URL
348572045Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0090196Source Record URL
274950916ChemFacesSource URLSource DetailCFN99234Source Record URL
317213370MolPortSource URLSource DetailMolPort-039-338-103Source Record URL