beta-sitosterol

  • GreenMolBD CID : 127
  • Molecular Formula : C29H50O
  • Molecular Weight : 414.718
  • Exact Molecular Mass : 414.386
  • IUPAC Name : (3S,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]phenanthren-3-ol
  • InChI : InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
  • InChI Key : KZJWDPNRJALLNS-VJSFXXLFSA-N
  • Canonical SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
  • Isomeric SMILES : CCC(CCC(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
8.0248 20.23 1 1 30 6 0 0 12.8217 669.378 454.665 0.619557

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-231.012321 1.64 -4.187 -9.45408 1.07947 5.267

4. Compound Reactivity

DLP nRFG nLMR
6 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 1.57193 15055.6 0.0017317 Moderate Weak None Degradable 3.35E-6 0.217316

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
BETA-SITOSTEROL
Sitosterol
83-46-5
Cupreol
Quebrachol
22,23-Dihydrostigmasterol
Azuprostat
Triastonal
Cinchol
Rhamnol
Harzol
beta-Sitosterin
B-Sitosterol
alpha-Dihydrofucosterol
Nimbosterol
Stigmast-5-en-3beta-ol
Sito-Lande
(-)-beta-Sitosterol
(3beta)-Stigmast-5-en-3-ol
Angelicin (steroid)
24alpha-Ethylcholesterol
a-Dihydrofucosterol
.beta.-Sitosterin
.beta.-Sitosterol
Prostasal
NSC8096
(24R)-Stigmast-5-en-3beta-ol
SITOSTEROL, BETA
.alpha.-Dihydrofucosterol
(24R)-Ethylcholest-5-en-3beta-ol
24.alpha.-Ethylcholesterol
Stigmast-5-en-3-ol
Stigmast-5-en-3.beta.-ol
UNII-S347WMO6M4
Sobatum
CHEMBL221542
S347WMO6M4
Stigmasterol, 22,23-dihydro-
CHEBI:27693
Stigmast-5-en-3-ol, (3b)-
C29H50O
Stigmast-5-en-3-ol, (3beta)-
NSC49083
SKF 14463
Stigmasterol,23-dihydro-
Betaprost
Stigmast-5-en-3-ol, (3.beta.)-
24beta-Ethylcholesterol
5-Stigmasten-3beta-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,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]phenanthren-3-ol
14-((1S,4R)-4-ethyl-1,5-dimethylhexyl)(1S,5S,10S,11S,2R,14R,15R)-2,15-dimethyl tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
64997-52-0
68555-08-8
24-alpha-Ethylcholesterol
Stigmast-5-en-3-beta-ol
delta5-Stigmasten-3-beta-ol
CCRIS 5529
(3-beta)-Stigmast-5-en-3-ol
beta Sitosterol
Sitosterol beta
a-Phytosterol
NSC 8096
b-Sitosterin
beta-Phytosterol
Beta-sistosterol
EINECS 201-480-6
MFCD00003631
alpha-Phytosterol
.beta.Sitosterin
.beta.Sitosterol
Steroids, hydroxy
CAS-83-46-5
Refined soy sterol
NCGC00095716-01
(-)-b-Sitosterol
AI3-26020
Harzol (TN)
24a-Ethylcholesterol
alpha.Dihydrofucosterol
D5-Stigmasten-3b-ol
Stigmast-5-en-3b-ol
AC1L5BKV
Prestwick0_000985
Prestwick1_000985
Prestwick2_000985
Prestwick3_000985
Delta5-Stigmasten-3b-ol
SITOSTEROL, BETA-
DSSTox_CID_2481
bmse000477
D0Y7LD
beta-Sitosterol, >=70%
beta-Sitosterol (Synthetic)
DSSTox_RID_76601
BIDD:PXR0121
DSSTox_GSID_22481
SCHEMBL16105
22,23-dihydro-Stigmasterol
BSPBio_001049
ARONIS24293
BIDD:ER0636
SPBio_002950
BPBio1_001155
MEGxp0_001710
Soybean oil sterols phytosterols
DTXSID5022481
(24R)-Stigmast-5-en-3b-ol
ACon1_000287
CTK3E8043
BBC/449
KZJWDPNRJALLNS-VJSFXXLFSA-N
MolPort-001-742-476
HMS1571E11
HMS2098E11
(24R)-Ethylcholest-5-en-3b-ol
17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
24-Ethylcholest-5-en-3.beta.-ol
HY-N0171
NSC-8096
NSC18173
ZINC4095717
beta-Sitosterol, analytical standard
EINECS 271-413-3
Tox21_111514
ANW-41688
BDBM50218197
beta-Sitosterol, synthetic, >=95%
LMST01040129
NSC-18173
NSC-49083
s2273
SBB012603
AKOS005267194
CCG-208334
CS-6009
MCULE-2409753351
beta-Sitosterol, from soybean, >=96%
SMP1_000274
NCGC00142598-02
NCGC00142598-03
AC-24183
AN-24063
AN-38045
BC201729
BT000709
M047
NCI60_041777
PL000959
SC-19725
SC-57983
ST069312
AB0015024
LS-195633
TR-037936
AB00513984
N1688
S0040
C01753
D08518
AA-504/07226009
SR-05000002307
I06-1624
Q-200712
SR-05000002307-3
8295076E-C876-4B41-ADF5-02A644EEA34F
beta-Sitosterol, analytical standard, from soybean, >=40%
beta-Sitosterol, primary pharmaceutical reference standard
Beta-sitosterol, European Pharmacopoeia (EP) Reference Standard
beta-Sitosterol, United States Pharmacopeia (USP) Reference Standard
beta-Sitosterol, certified reference material, 100 mug/mL in chloroform
(1S,2R,5S,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-EN-5-OL
(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-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
15764-35-9
182512-23-8
76772-70-8
Stigmasterol,22,23-dihydro
Sitosterol/beta-Sitosterol
BG01125081
SR-05000002307-2
Phytosterol
UNII-3OE0DD1I5J component KZJWDPNRJALLNS-VJSFXXLFSA-N

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
beta-sitosterol
Abelmoschus esculentus (L.) Moench 5
Abutilon indicum (L.) Sw. Leaf; Root; Whole Plant 3 , 5 , 6 , 9 , 10 , 11
Acalypha indica L. Leaf 2 , 4
Ageratum conyzoides L Stem; Leaf; Aerial 9 , 10 , 20
Ammannia baccifera L. 6
Amoora rohituka (Roxb.) Wight & Arn. 14
Andrographis paniculata Whole Plant 6 , 18 , 22
Anthocephalus chinesis (Lamk.) Rich. Ex Walp. Stem Bark; Leaf 1 , 3 , 7 , 11
Arachis hypogea L. Seed 3 , 2
Areca catechu L. Fruit; Root 9 , 2 , 12 , 17
Avicennia marina Leaf 3 , 8 , 6
Azadirachta indica A. juss. Leaf; Seed; Fruit 28 , 54 , 68
Bauhinia variegate Stem 1 , 2
Boerhavia diffusa L. Root 2 , 10
Borassus flabellifer L. Flower 4
Cocculus hirsutus L. Leaf 4 , 3
Colocasia esculenta Linn. Bark 3
Coriandrum sativum Linn. 38
Crataeva nurvala Stem Bark, Root bark 4 , 6 , 7
Crinum latifolium L.  Leaf 2
Croton oblongifolius  Aerial 3
Croton tiglium L.  Leaf 10
Curcuma amada Rhizome 11
Cuscuta reflexa 5
Cyperus rotundus L Tuber 23 , 11 , 2 , 3
Desmodium pulchellum Benth Root 7
Duabanga grandiflora Stem Bark; Stem 1
Ficus elastica Bark of Aerial Root 3
Flacourtia indica Heartwood; Stem Bark; Twig 5 , 11
Garcinia cowa Roxb Fruit; Stem 7
Garuga pinnata Roxb. Stem Bark 8
Gloriosa superba L. 6
Hemidesmus indicus br. Root; Whole Plant; Stem 12 , 13 , 10 , 14
Hygrophila auriculata Leaf 3 , 2
Ichnocarpus frutescens Stem 3
Ipomoea aquatica Seed 12
Ipomoea batatas (L.) Lam. Root 4 , 5
Ipomoea cairica (L.) Sweet Aerial 2
Ixora coccinea L.  Leaf; Aerial; Flower 1 , 3 , 6 , 5 , 7 , 8
Jasminum graniflorum Leaf 12
Juglans regia Fruit 11 , 4 , 3 , 17 , 18
Kleinhovia hospita L.  Leaf and Twig 6
Lagenaria siceraria (Molina) Standl.  Fruit 2 , 6 , 12
Leea indica Leaf 2
Lepidium sativum Seed 1
Leucas aspera Root; Whole Plant; Shoot; Aerial 8 , 15 , 7 , 17 , 21
Limnophila indica Aerial Part and Root 8 , 2
Lippia nodiflora (L.) Aerial 5
Ludwigia octovalvis 1
Mangifera indica Fruit 4
Marsilea quadrifolia 4
Melastoma malabathricum Leaf; Root 4 , 10 , 11 , 12
Melothria heterophylla Aerial 6
Microcos paniculata Leaf 9
Oryza sativa L. Bran 4
Rhinacanthus communis Root 2 , 7
Rhizophora apiculata Heartwood; Root 6 , 7
Ricinus communis Leaf 10 , 4
Scoparia dulcia L Root 15
Sesamum indicum L. 15
Tamarindus indica Leaf; Kernel; Root 1 , 5 , 11 , 4
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
156 Cytochrome P450 2D6 Homo sapiens >100000 10.1021/np030556a 15270556
157 Cytochrome P450 3A4 Homo sapiens >100000 10.1021/np030556a 15270556
158 cytochrome P450 family 2 subfamily D member 6 CYP2D6 Homo sapiens 100 402937
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 100 402936
159 dipeptidyl peptidase 4 DPP4 Homo sapiens 28.84 1118023
11 DNA polymerase beta Homo sapiens 26300 10.1021/np0301893 14640519

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
349344183Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0862325Source Record URL
329747386Sigma-AldrichSource URLSource Detail02090580_SIALSource Record URL
329751100Sigma-AldrichSource URLSource Detail1612947_USPSource Record URL
329756360Sigma-AldrichSource URLSource Detail43623_SIALSource Record URL
24870722Sigma-AldrichSource URLSource Detail47133_SUPELCOSource Record URL
329769380Sigma-AldrichSource URLSource Detail85451_SIGMASource Record URL
24899468Sigma-AldrichSource URLSource DetailS1270_SIGMASource Record URL
329824552Sigma-AldrichSource URLSource DetailS5753_SIALSource Record URL
24899862Sigma-AldrichSource URLSource DetailS9889_SIGMASource Record URL
329831512Sigma-AldrichSource URLSource DetailY0001615_SIALSource Record URL
162037848Chembase.cnSource URLSource Detail72928Source Record URL
319040415Chem-Space.com DatabaseSource URLSource DetailCSC020619659Source Record URL
162725248ChemTikSource URLSource DetailCTK3E8043Source Record URL
57399980NovoSeekSource URLSource Detail222284Source Record URL
126658132ChemMolSource URLSource Detail44000925Source Record URL
126685076ChemMolSource URLSource Detail49423726Source Record URL
126603578ChemMolSource URLSource Detail80101445Source Record URL
223682596AN PharmaTechSource URLSource DetailAN-24063Source Record URL
223678840AN PharmaTechSource URLSource DetailAN-38045Source Record URL
316410430abcr GmbHSource URLSource DetailAB141610Source Record URL
252345939AHH Chemical co.,ltdSource URLSource DetailMT-47868Source Record URL
88785461MolPortSource URLSource DetailMolPort-001-742-476Source Record URL
162180457AK Scientific, Inc. (AKSCI)Source URLSource DetailM047Source Record URL
163614517ApexBio TechnologySource URLSource DetailN1688Source Record URL
340515955LGC StandardsSource URLSource DetailLGCFOR0837.00Source Record URL
340520133LGC StandardsSource URLSource DetailMM0837.00Source Record URL
3134392ChemExper Chemical DirectorySource URLSource Detailigp``@@LbbRfTRrTtRLVTTUNRt{t\uTuUUUUUUUUR`|YNfuybeah@Source Record URL
204356544TractusSource URLSource DetailTR-037936Source Record URL
369356254AmbinterSource URLSource DetailAmb17776567Source Record URL
348354258AbMole BioscienceSource URLSource DetailM4163Source Record URL
312598520Oakwood ProductsSource URLSource Detail099257Source Record URL
143401628TimTecSource URLSource DetailSBB012603Source Record URL
124570889TimTecSource URLSource DetailST069312Source Record URL
92251521ISpharmSource URLSource DetailI06-1624Source Record URL
115354337AronisSource URLSource DetailARONIS24293Source Record URL
131549821AKos Consulting & SolutionsSource URLSource DetailAKOS005267194Source Record URL
316903361Hangzhou APIChem TechnologySource URLSource DetailAC-24183Source Record URL
347913067SelleckchemSource URLSource DetailS2273Source Record URL
196110416BoerchemSource URLSource DetailBC201729Source Record URL
290044868Aurora Fine Chemicals LLCSource URLSource DetailK05.570.361Source Record URL
3567512321717 CheMall CorporationSource URLSource DetailBG01125081Source Record URL
3598942731717 CheMall CorporationSource URLSource DetailBG06738452Source Record URL
255369825BiosynthSource URLSource DetailQ-200712Source Record URL
342415072Wubei-BiochemSource URLSource DetailWB006899SUSource Record URL
319884231MedChemexpress MCESource URLSource DetailHY-N0171Source Record URL
319885178AbaChemSceneSource URLSource DetailCS-6009Source Record URL
312695715TargetMolSource URLSource DetailT2966Source Record URL
160809188AnwardSource URLSource DetailANW-41688Source Record URL
113475760ABI ChemSource URLSource DetailAC1L5BKVSource Record URL
252220303Race ChemicalSource URLSource DetailRV022508933Source Record URL
29204577R&D ChemicalsSource URLSource Detail3579Source Record URL
318241357Yuhao ChemicalSource URLSource DetailLT7005Source Record URL
87575667TCI (Tokyo Chemical Industry)Source URLSource DetailS0040Source Record URL
253652379labseekerSource URLSource DetailSC-19725Source Record URL
318168638labseekerSource URLSource DetailSC-57983Source Record URL
223387829Assembly Blocks Pvt. Ltd.Source URLSource DetailAB0015024Source Record URL
252256690Wilshire TechnologiesSource URLSource Detailbeta-SitosterolSource Record URL
252951230MculeSource URLSource DetailMCULE-2409753351Source Record URL
257139570ZINCSource URLSource DetailZINC4095717Source Record URL
318504725CambridgeChemSource URLSource DetailCB11041Source Record URL
346692810LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00192871Source Record URL
315444191Phion LtdSource URLSource Detail32447958Source Record URL
347808709Alfa ChemistrySource URLSource Detail19044-06-5Source Record URL
274951038ChemFacesSource URLSource DetailCFN99916Source Record URL