Stigmasterol

  • GreenMolBD CID : 116
  • Molecular Formula : C29H48O
  • Molecular Weight : 412.702
  • Exact Molecular Mass : 412.371
  • IUPAC Name : (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • 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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
  • InChI Key : HCXVJBMSMIARIN-PHZDYDNGSA-N
  • Canonical SMILES : CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
  • Isomeric SMILES : CCC(/C=C/C(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)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; 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; 3-beta-hydroxysteroid; 3-beta-hydroxy-delta-5-steroid; 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
7.8008 20.23 1 1 30 5 0 0 12.8123 663.477 453.241 0.622029

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-195.88977 1.51 -4.126 -9.32613 1.07337 5.2

4. Compound Reactivity

DLP nRFG nLMR
6 0 5

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 1.15729 13462.4 0.0012663 Moderate Weak Mild Degradable 6.31E-6 0.247568

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
STIGMASTEROL
Stigmasterin
83-48-7
beta-Stigmasterol
Stigmasta-5,22-dien-3beta-ol
(24S)-5,22-Stigmastadien-3beta-ol
UNII-99WUK5D0Y8
CHEBI:28824
Stigmasta-5,22E-dien-3beta-ol
Stigmasta-5,22-dien-3-beta-ol
MFCD00003630
ST069313
(3beta,22E)-Stigmasta-5,22-dien-3-ol
Stigmasta-5,22-dien-3-ol, (3b,22E)-
Stigmasta-5,22-dien-3-ol, (3beta,22E)-
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
NSC 8095
.beta.-Stigmasterol
.delta.5,22-Stigmastadien-3.beta.-ol
14-((2E)(4S,1R)-4-ethyl-1,5-dimethylhex-2-enyl)(1S,5S,10S,11S,2R,14R,15R)-2,15 -dimethyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
Stigmasta-5,22-dien-3-ol
5,22-Stigmastadien-3beta-ol
b-stigmasterol
NSC-8095
D5-Stigmasterol
Delta5-Stigmasterol
3beta-Hydroxy-24-ethyl-5,22-cholestadiene
AC1NQXLK
Stigmasterol, ~95%
SCHEMBL23999
stigmasta-5,22t-dien-3b-ol
99WUK5D0Y8
CCRIS 7476
CHEMBL400247
stigmasta-5,22-dien-3-b-ol
HSDB 7683
HCXVJBMSMIARIN-PHZDYDNGSA-N
MolPort-004-956-055
Delta5,22-Stigmastadien-3beta-ol
HY-N0131
ZINC4096712
EINECS 201-482-7
(24S)-5,22-stigmastadien-3b-ol
BDBM50376364
BI4664
LMST01040123
SBB012602
24aFH-stigmasta-5,22t-dien-3b-ol
AKOS022168193
CS-7746
(22E)-stigmasta-5,22-dien-3beta-ol
(24S)-Stigmast-5,22-dien-3beta-ol
(24xH)-stigmasta-5,22t-dien-3b-ol
24-Ethyl-5,22-cholestadien-3beta-ol
5,22-Cholestadien-24-ethyl-3beta-ol
Stigmasta-5,22-dien-3beta-ol (8CI)
(24aFH)-stigmasta-5,22t-dien-3b-ol
(24x)-ethylcholesta-5,22-dien-3b-ol
Stigmasta-5,22-dien-3-ol, (3beta)-
(3b,22E)-stigmasta-5,22-dien-3-ol
24x-24-ethylcholest-5,22-dien-3b-ol
AN-42262
BT000705
DR002482
P501
PL071424
SC-18170
24-Ethyl-5,22-cholestadien-3.beta.-ol
rac-(24xH)-stigmasta-5,22t-dien-3b-ol
Stigmasta-5,22-dien-3-ol,(3b,22E)-
(3.beta.,22E)-Stigmasta-5,22-dien-3-ol
(24S)-24-Ethylcholesta-5,22-dien-3beta-ol
C05442
157542-EP2277507A1
157542-EP2286795A1
Q-201746
Stigmasta-5,22-dien-3-ol, (3beta,22E)- (9CI)
Stigmasterol, certified reference material, 10 mg/mL in chloroform
(1S,2R,5S,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-7-EN-5-OL
(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
17-(4-ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
AS-15473
UNII-3OE0DD1I5J component HCXVJBMSMIARIN-PHZDYDNGSA-N

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Stigmasterol
Abelmoschus esculentus (L.) Moench 4
Abutilon indicum (L.) Sw. Whole Plant; Leaf 10 , 11
Acalypha indica L. Leaf 2
Ageratum conyzoides L Stem; Leaf; Aerial 9 , 10 , 20
Amoora rohituka (Roxb.) Wight & Arn. 14
Arachis hypogea L. Seed 3 , 2
Asparagus racemosus L. Fruit 5
Avicennia marina Leaf; Aerial Root 6 , 7 , 8
Azadirachta indica A. juss. Leaf 28
Coriandrum sativum Linn. 39 , 40
Crataeva nurvala Stem Bark 4
Crinum latifolium L.  Leaf 2
Croton tiglium L.  Seed 6
Cuscuta reflexa 5
Ficus elastica Bark of Aerial Root 3
Garcinia cowa Roxb Stem 7
Hygrophila auriculata 4 , 2
Ipomoea batatas (L.) Lam. Root 4
Ixora coccinea L.  Aerial 6 , 8
Juglans regia Fruit; Leaf 4 , 9
Lepidium sativum Seed 1
Leucas aspera Root 8
Lippia nodiflora (L.) Aerial 4
Mangifera indica Fruit 4
Microcos paniculata Leaf 9
Oryza sativa L. Bran 4
Rhinacanthus communis Root 7
Rhizophora apiculata Heartwood 6
Ricinus communis Leaf 10 , 4 , 5
Rumex vesicarius Aerial 3
Tamarindus indica Kernel 4 , 5
Viola odorata 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
11 DNA polymerase beta Homo sapiens 60280 10.1016/j.bmc.2008.02.071 18343122
11 DNA polymerase beta Homo sapiens >250000 10.1016/j.bmc.2008.02.071 18343122
11 DNA polymerase beta Homo sapiens 43400 10.1021/np0301893 14640519

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
342415070Wubei-BiochemSource URLSource DetailWB006897SUSource Record URL
255370643BiosynthSource URLSource DetailQ-201746Source Record URL
257139770ZINCSource URLSource DetailZINC4096712Source Record URL
354289685Chemenu Inc.Source URLSource DetailCM116219Source Record URL
354268938Key Organics/BIONETSource URLSource DetailAS-15473Source Record URL
315446248Phion LtdSource URLSource Detail73724057Source Record URL
348352305AbaChemSceneSource URLSource DetailCS-7746Source Record URL
252403634MolepediaSource URLSource DetailM90001485PSource Record URL
29204591R&D ChemicalsSource URLSource Detail3537Source Record URL
318358271CambridgeChemSource URLSource DetailDB25819Source Record URL
113854003ABI ChemSource URLSource DetailAC1NQXLKSource Record URL
57357876NovoSeekSource URLSource Detail5280794Source Record URL
162183545AK Scientific, Inc. (AKSCI)Source URLSource DetailP501Source Record URL
215767596AKos Consulting & SolutionsSource URLSource DetailAKOS022168193Source Record URL
251883973labseekerSource URLSource DetailSC-18170Source Record URL
346688376LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00185193Source Record URL
252359194AHH Chemical co.,ltdSource URLSource DetailAPI-1531Source Record URL
316410497abcr GmbHSource URLSource DetailAB141708Source Record URL
223682597AN PharmaTechSource URLSource DetailAN-42262Source Record URL
24870720Sigma-AldrichSource URLSource Detail47132_SUPELCOSource Record URL
24899523Sigma-AldrichSource URLSource DetailS2424_SIGMASource Record URL
310280299Glentham Life Sciences Ltd.Source URLSource DetailGP5909Source Record URL
143401627TimTecSource URLSource DetailSBB012602Source Record URL
124570890TimTecSource URLSource DetailST069313Source Record URL
252450020Wilshire TechnologiesSource URLSource Detailbeta-StigmasterolSource Record URL
254761906Boc SciencesSource URLSource Detail83-48-7Source Record URL
321935187AcadechemSource URLSource DetailACDS-065517Source Record URL
252216341Race ChemicalSource URLSource DetailRV022504971Source Record URL
274953058ChemFacesSource URLSource DetailCFN97326Source Record URL
347832011MedChemexpress MCESource URLSource DetailHY-N0131Source Record URL
3598917891717 CheMall CorporationSource URLSource DetailBG06735968Source Record URL
3134395ChemExper Chemical DirectorySource URLSource Detailigp``@@LbbRfTRrTtRLVTTUNRt{t\uTuUUUUSUUUR`|YNfuybeajAj@Source Record URL
92466046MolPortSource URLSource DetailMolPort-004-956-055Source Record URL
162037906Chembase.cnSource URLSource Detail72986Source Record URL
350089460DC ChemicalsSource URLSource DetailDCD-042Source Record URL
349909645Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM1427790Source Record URL
319040446Chem-Space.com DatabaseSource URLSource DetailCSC020619759Source Record URL