Daucosterol

  • GreenMolBD CID : 128
  • Molecular Formula : C35H60O6
  • Molecular Weight : 576.859
  • Exact Molecular Mass : 576.439
  • IUPAC Name : (2R,3R,4S,5S,6R)-2-[[(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-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  • InChI : InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24+,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1
  • InChI Key : NPJICTMALKLTFW-OFUAXYCQSA-N
  • Canonical SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)C
  • Isomeric SMILES : CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)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; Steroidal glycosides; Delta-5-steroids; Hexoses; O-glycosyl compounds; Oxanes; Secondary alcohols; Polyols; Oxacyclic compounds; Acetals; Primary alcohols; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic heteropolycyclic compounds

1.5. Substituents

C24-propyl-sterol-skeleton; Triterpenoid; Stigmastane-skeleton; Steroidal glycoside; Delta-5-steroid; Hexose monosaccharide; Glycosyl compound; O-glycosyl compound; Oxane; Monosaccharide; Secondary alcohol; Polyol; Oxacycle; Acetal; Organoheterocyclic compound; Primary alcohol; Organooxygen compound; Alcohol; Hydrocarbon derivative; Organic oxygen compound; Aliphatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
5.849 99.38 4 6 41 9 0 0 16.085 848.947 589.531 0.6795

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-458.610383 3.43 -4.184 -9.43759 1.0704 5.254

4. Compound Reactivity

DLP nRFG nLMR
2 1 6

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 1.69035 1021.02 0.00181455 Moderate None Severe Degradable 1.98E-5 0.152622

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No Yes No Yes Yes Yes Yes

7. Synonyms

Name
Daucosterol
Sitogluside
Eleutheroside A
Alexandrin
beta-Sitosterol glucoside
474-58-8
Coriandrinol
Daucosterin
Sitoglusidum
Doursterol
Sterolin
BSSG
beta-Daucosterol
WA 184
UNII-U45VN859W3
ELEUTHEROSIDEA
AC1NX3NW
Sitogluside (USAN/INN)
3-beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
beta-sitosteryl-beta-D-glucopyranoside
EU-4906
Ambap474-58-8
CHEMBL506678
CHEBI:67554
Sitosterol-3-O-beta-D-glucoside
U45VN859W3
Sitosteryl glycoside
NSC-165962
Sitosterol D-glucoside
beta-sitosterol 3-O-beta-D-glucopyranoside
beta-Sitosteryl glucoside
(-)-beta-Sitosterol-beta-D-glucopyranoside
Sitogluside [USAN:INN]
Sitoglusidum [INN-Latin]
D05848
Sitoglusido [INN-Spanish]
beta-Sitosterol monoglucoside
(3beta)-stigmast-5-en-3-yl beta-D-glucopyranoside
.beta.-D-Glucopyranoside, (3.beta.)-stigmast-5-en-3-yl
Sitoglusido
AW 10
NSC165962
NSC 165962
EU 4906
BRN 4359450
(2R,3R,4S,5S,6R)-2-[[(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-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
sitosterol glucuronide
3beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
(3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside
beta-sitosterol glucutonide
sitosterol beta-D-glucoside
beta-sitosterol-beta-D-glycoside
Eleutheroside A
C35H60O6
FT-0686600
CID5742590
Stigmast-5-ene, 3-beta-(beta-D-glucopyranosyloxy)-
beta-D-Glucopyranoside, (3beta)-stigmast-5-en-3-yl
SureCN137210
beta-Sitosterol D-glucoside
C011015
SCHEMBL137210
MolPort-020-005-907
NPJICTMALKLTFW-OFUAXYCQSA-N
HY-N0410
BDBM50257635
ZINC49888788
CS-5421
BT000952
CA009528
CA009996
PL002051
AB0093074
N2296
W2339
C20785
Daucosterol (beta-Sitosterol beta-D-Glucoside)
474D588
Q-100502
oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2R,3R,4S,5S,6R)-2-(((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-yl)
(2R,3R,4S,5S,6R)-2-((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-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2R,3R,4S,5S,6R)-2-[[(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-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
(2R,3R,4S,5S,6R)-2-{[(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-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
beta-Sitosterol-3-O-beta-glucopyranoside
Lyoniside
Sitosterol-beta-D-glucoside
beta-Sistosterol glucoside
beta-Sitosterol-3-O-beta-D-glucopyranoside
AKOS032962016
BG01493083

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Daucosterol
Abelmoschus esculentus (L.) Moench 5
Abutilon indicum (L.) Sw. 6
Acalypha indica L. Leaf 2 , 4
Ammannia baccifera L. Whole Plant 4
Amoora rohituka (Roxb.) Wight & Arn. Bark 16
Arachis hypogea L. Root 4
Asparagus racemosus L. Fruit 5
Borassus flabellifer L. Flower 4
Coriandrum sativum Linn. 37
Croton oblongifolius  Aerial 3
Duabanga grandiflora Stem Bark 2
Flacourtia indica Stem Bark; Twig 1 , 11
Garcinia cowa Roxb Fruit; Stem 7
Gloriosa superba L. Leaf 6
Jasminum sambac L. Root 12 , 9
Juglans regia Leaf 17 , 18
Kleinhovia hospita L.  Leaf and Twig 6
Ludwigia octovalvis 1
Manihot esculenta
Melastoma malabathricum Leaf 5 , 4
Sesamum indicum L. 15

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
2 aldo-keto reductase family 1 member B Akr1b1 Rattus norvegicus 30 654333
160 Aldose reductase Rattus norvegicus >30000 10.1021/np200646e 22264115
11 DNA polymerase beta Homo sapiens 26500 10.1021/np030531b 15165161
161 Sortase A (SrtA) Staphylococcus aureus 31720 10.1016/j.bmc.2009.02.008 19269184

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
354330212TargetMolSource URLSource DetailT3871Source Record URL
274951790ChemFacesSource URLSource DetailCFN98713Source Record URL
254777487Boc SciencesSource URLSource Detail474-58-8Source Record URL
251917079AvaChem ScientificSource URLSource Detail2271Source Record URL
251915729AvaChem ScientificSource URLSource Detail474-58-8Source Record URL
3566192371717 CheMall CorporationSource URLSource DetailBG01493083Source Record URL
349071363Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0589509Source Record URL
349071364Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0589510Source Record URL
349071365Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0589511Source Record URL
57365007NovoSeekSource URLSource Detail5742590Source Record URL
329978001Acorn PharmaTech Product ListSource URLSource DetailACN-035420Source Record URL
350089579DC ChemicalsSource URLSource DetailDCH-003Source Record URL
223397866Assembly Blocks Pvt. Ltd.Source URLSource DetailAB0093074Source Record URL
355397433AKos Consulting & SolutionsSource URLSource DetailAKOS032962016Source Record URL
255345088BiosynthSource URLSource DetailQ-100502Source Record URL
330384108ZINCSource URLSource DetailZINC49888788Source Record URL
341841538OChemSource URLSource Detail11410Source Record URL
252551451AK Scientific, Inc. (AKSCI)Source URLSource DetailW2339Source Record URL
252215256Race ChemicalSource URLSource DetailRV022503886Source Record URL
313035805MedChemexpress MCESource URLSource DetailHY-N0410Source Record URL
114106799ABI ChemSource URLSource DetailAC1NX3NWSource Record URL
355037074MuseChemSource URLSource DetailI003647Source Record URL
318465189Herbest Bio-TechSource URLSource DetailHS230674Source Record URL
241079457ChemMolSource URLSource Detail99088561Source Record URL
318156775ApexBio TechnologySource URLSource DetailN2296Source Record URL
347260576LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01345122Source Record URL
319554501AbovChem LLCSource URLSource DetailHY-N0410Source Record URL
313035922AbaChemSceneSource URLSource DetailCS-5421Source Record URL
188932933MolPortSource URLSource DetailMolPort-020-005-907Source Record URL