Lupeol acetate

  • GreenMolBD CID : 2058
  • Molecular Formula : C32H52O2
  • Molecular Weight : 468.766
  • Exact Molecular Mass : 468.397
  • 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-yl] acetate
  • InChI : InChI=1S/C32H52O2/c1-20(2)22-12-15-29(6)18-19-31(8)23(27(22)29)10-11-25-30(7)16-14-26(34-21(3)33)28(4,5)24(30)13-17-32(25,31)9/h22-27H,1,10-19H2,2-9H3/t22-,23+,24-,25+,26-,27+,29+,30-,31+,32+/m0/s1
  • InChI Key : ODSSDTBFHAYYMD-YOJQYFTNSA-N
  • Canonical SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C)C)C
  • Isomeric SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C)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; Carboxylic acid esters; Monocarboxylic acids and derivatives; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; Steroid; Carboxylic acid ester; Monocarboxylic acid or derivatives; Carboxylic acid derivative; Organic oxygen compound; Organic oxide; Hydrocarbon derivative; Organooxygen compound; Carbonyl group; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
8.5956 26.3 0 2 34 3 0 0 14.0197 732.088 518.989 0.640314

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-266.699834 2.1 -4.372 -9.8185 1.07516 5.447

4. Compound Reactivity

DLP nRFG nLMR
5 1 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 4.5056 4942.45 0.00303989 Moderate Weak None Degradable 7.54E-7 0.0344296

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 acetate
Lupeyl acetate
3-Acetyllupeol
1617-68-1
LUPENYL ACETATE
CHEBI:69744
3-O-Acetyllupeol
UNII-WJ3A89G0H6
EINECS 216-575-8
NSC 281806
AC1L3NJG
Lup-20(29)-en-3-ol, acetate, (3beta)-
SCHEMBL936136
CHEMBL453802
WJ3A89G0H6
ZINC4097722
MFCD00017362
LMPR0106130002
AJ-48008
CC-30087
DR002910
PL047620
Lup-20(29)-en-3beta-ol, acetate (8CI)
C08630
C-22685
(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-YL ACETATE
[(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-yl] acetate
[(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-yl] acetate
Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Lupeol acetate
Crataeva nurvala Root Bark 7
Hemidesmus indicus br. Root; Stem 12 , 10
Ichnocarpus frutescens Stem 3 , 9

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

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
254767930Boc SciencesSource URLSource Detail1617-68-1Source Record URL
330114316ZINCSource URLSource DetailZINC4097722Source Record URL
223557179A&J Pharmtech CO., LTD.Source URLSource DetailAJ-48008Source Record URL
355177408MuseChemSource URLSource DetailM123588Source Record URL
316427154abcr GmbHSource URLSource DetailAB166435Source Record URL
29204346R&D ChemicalsSource URLSource Detail0024Source Record URL
368522244AmbinterSource URLSource DetailAmb10845315Source Record URL
104406681ABI ChemSource URLSource DetailAC1L3NJGSource Record URL
348812832Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0330983Source Record URL
3632552251717 CheMall CorporationSource URLSource DetailBG08012556Source Record URL
318267462Chem-Space.com DatabaseSource URLSource DetailCSC000052552Source Record URL
57335146NovoSeekSource URLSource Detail92157Source Record URL