Lupeol

  • GreenMolBD CID : 114
  • Molecular Formula : C30H50O
  • Molecular Weight : 426.729
  • Exact Molecular Mass : 426.386
  • IUPAC Name : (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
  • InChI : InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
  • InChI Key : MQYXUWHLBZFQQO-QGTGJCAVSA-N
  • Canonical SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C
  • Isomeric SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

1.2. Taxonomy Tree

1.3. Alternative Parent

Steroids and steroid derivatives; Secondary alcohols; Cyclic alcohols and derivatives; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; Steroid; Cyclic alcohol; Secondary alcohol; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Alcohol; 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 31 1 0 0 13.065 679.912 474.757 0.627624

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-213.12124 1.53 -4.381 -9.79876 1.03613 5.417

4. Compound Reactivity

DLP nRFG nLMR
5 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 2.20592 6970.18 0.00302944 Moderate Weak None Degradable 9.66E-6 0.326549

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
Lupeol
545-47-1
Fagarasterol
Clerodol
Monogynol B
farganasterol
beta-Viscol
Triterpene lupeol
Fagarsterol
Lupenol
UNII-O268W13H3O
Lup-20(29)-en-3b-ol
CHEBI:6570
.beta.-Viscol
MQYXUWHLBZFQQO-QGTGJCAVSA-N
O268W13H3O
NSC90487
MFCD00017351
AK105935
20(29)-Lupen-3beta-ol
20[29]-Lupen-3beta-ol
Lup-20(29)-en-3.beta.-ol
EINECS 208-889-9
NSC 90487
(3-beta)-Lup-20(29)-en-3-ol
Lup-20(29)-en-3-ol, (3beta)-
Lup-20(29)-en-3-ol, (3.beta.)-
Monogynol B (6CI)
HSDB 7687
Lup-20(29)-en-3-ol, (3-beta)-
Lupeol, >=94%
Lupeol, analytical standard
AC1L61YJ
Ambap545-47-1
SCHEMBL148518
CHEMBL289191
KS-00000KMW
MolPort-006-111-741
HY-N0790
ZINC4081455
(3beta)-lup-20(29)-en-3-ol
BDBM50377927
NSC-90487
AKOS016008524
CS-7563
DB12622
LMPR0106130001
Lup-20(29)-en-3beta-ol (8CI)
Lup-20(29)-en-3-beta-ol (8CI)
AJ-47897
BT000742
CC-30086
NCI60_042005
PL059143
AX8034045
N1291
ST24047509
V0212
(3|A,13|I)-Lup-20(29)-en-3-ol
C08628
545L471
C-22186
Q-100615
(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-HEXAMETHYL-8-(PROP-1-EN-2-YL)PENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(1)?]HENICOSAN-17-OL
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Lupeol
Abelmoschus esculentus (L.) Moench 4
Acacia nilotica (L.) Wild. Leaf 11
Ammannia baccifera L. Aerial 1
Avicennia marina Leaf; Aerial Root; Aerial 3 , 6 , 7 , 14
Bauhinia variegate Stem 1 , 2
Cocculus hirsutus L. Leaf 4
Crataeva nurvala Stem Bark, Bark, Root Bark 1 , 2 , 3 , 4 , 5 , 6 , 7
Cucumis sativus L. Seed 6
Helianthus annuus Flower 4
Hemidesmus indicus br. Root 12 , 7
Hygrophila auriculata Root 4 , 2 , 5
Ichnocarpus frutescens Stem 3
Ixora coccinea L.  Leaf; Aerial; Flower 1 , 3 , 5 , 6 , 7 , 8 , 9
Juglans regia Leaf 17 , 18
Leea indica Leaf 2 , 3
Mangifera indica Fruit 4
Rhinacanthus communis Leaf; Stem; Root 1 , 2 , 4 , 7
Rhizophora apiculata Stem; Root 4 , 7
Ricinus communis Root; Stem; Seed; Aerial 1 , 2 , 3 , 4 , 5 , 30
Viola odorata 4
Zanthoxylum rhetsa Bark 4 , 8

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
136 DNA topoisomerase II alpha TOP2A Homo sapiens 250 480993
137 Topoisomerase II alpha (HuTopoIIα) 10400 11754608
137 Topoisomerase II alpha (HuTopoIIα) >250000 10.1016/j.bmcl.2010.03.063 20371180

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
354289443Chemenu Inc.Source URLSource DetailCM115977Source Record URL
297450624Aurora Fine Chemicals LLCSource URLSource DetailA13.110.472Source Record URL
252450004Wilshire TechnologiesSource URLSource DetailLupeolSource Record URL
162187575AK Scientific, Inc. (AKSCI)Source URLSource DetailV0212Source Record URL
355204498Key Organics/BIONETSource URLSource DetailDS-3391Source Record URL
29204345R&D ChemicalsSource URLSource Detail0017Source Record URL
57400729NovoSeekSource URLSource Detail259846Source Record URL
329751732Sigma-AldrichSource URLSource Detail18692_SIALSource Record URL
57654331Sigma-AldrichSource URLSource DetailL5632_ALDRICHSource Record URL
223557068A&J Pharmtech CO., LTD.Source URLSource DetailAJ-47897Source Record URL
249866656SyntreeSource URLSource DetailST24047509Source Record URL
336302722Angene ChemicalSource URLSource DetailAGN-PC-0SHLD2Source Record URL
255431826OXCHEM CORPORATIONSource URLSource DetailAX8034045Source Record URL
346696441LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00197930Source Record URL
350090286DC ChemicalsSource URLSource DetailDCY-038Source Record URL
348354794AbMole BioscienceSource URLSource DetailM4703Source Record URL
341837376OChemSource URLSource Detail7230Source Record URL
255345201BiosynthSource URLSource DetailQ-100615Source Record URL
329978300Acorn PharmaTech Product ListSource URLSource DetailACN-035752Source Record URL
335977330MolCoreSource URLSource DetailMC114952Source Record URL
162091434Chembase.cnSource URLSource Detail104262Source Record URL
330114043ZINCSource URLSource DetailZINC4081455Source Record URL
346425882King ScientificSource URLSource DetailKS-00000KMWSource Record URL
310275891Glentham Life Sciences Ltd.Source URLSource DetailGL2733Source Record URL
254779420Boc SciencesSource URLSource Detail545-47-1Source Record URL
252351418AHH Chemical co.,ltdSource URLSource DetailMT-53357Source Record URL
163847436AKos Consulting & SolutionsSource URLSource DetailAKOS016008524Source Record URL
275880653BePharm Ltd.Source URLSource DetailB34045Source Record URL
316427153abcr GmbHSource URLSource DetailAB166434Source Record URL
347832025MedChemexpress MCESource URLSource DetailHY-N0790Source Record URL
318265710Chem-Space.com DatabaseSource URLSource DetailCSC000048904Source Record URL
312695010TargetMolSource URLSource DetailT2895Source Record URL
348352334AbaChemSceneSource URLSource DetailCS-7563Source Record URL
252066183Bide Pharmatech Ltd.Source URLSource DetailBD34045Source Record URL
374089435Combi-BlocksSource URLSource DetailQP-3810Source Record URL
251911885AvaChem ScientificSource URLSource Detail1339Source Record URL
251914962AvaChem ScientificSource URLSource Detail545-47-1Source Record URL
349115741Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0633887Source Record URL
123121001MolPortSource URLSource DetailMolPort-006-111-741Source Record URL
355036078MuseChemSource URLSource DetailR048382Source Record URL
241094727ChemMolSource URLSource Detail99103831Source Record URL
103815666AAA ChemistrySource URLSource DetailAR-1I1460Source Record URL
104468680ABI ChemSource URLSource DetailAC1L61YJSource Record URL
163614484ApexBio TechnologySource URLSource DetailN1291Source Record URL
274951592ChemFacesSource URLSource DetailCFN98913Source Record URL
3599087581717 CheMall CorporationSource URLSource DetailBG06752937Source Record URL