Ursolic acid acetate

  • GreenMolBD CID : 2832
  • Molecular Formula : C32H50O4
  • Molecular Weight : 498.748
  • Exact Molecular Mass : 498.371
  • IUPAC Name : (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
  • InChI : InChI=1S/C32H50O4/c1-19-11-16-32(27(34)35)18-17-30(7)22(26(32)20(19)2)9-10-24-29(6)14-13-25(36-21(3)33)28(4,5)23(29)12-15-31(24,30)8/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23+,24-,25+,26+,29+,30-,31-,32+/m1/s1
  • InChI Key : PHFUCJXOLZAQNH-OTMOLZNZSA-N
  • Canonical SMILES : CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC(=O)C)C)C)C2C1C)C)C(=O)O
  • Isomeric SMILES : CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC(=O)C)C)C)C2C1C)C)C(=O)O
  • 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

Dicarboxylic acids and derivatives; Carboxylic acid esters; Carboxylic acids; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; Dicarboxylic acid or derivatives; Carboxylic acid ester; Carboxylic acid; 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
7.6603 63.6 1 4 36 3 0 0 14.2159 741.789 533.812 0.672358

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-344.91375 3.31 -4.2 -9.43735 1.03734 5.237

4. Compound Reactivity

DLP nRFG nLMR
4 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 0.981898 976.71 0.00267313 Moderate Weak None Degradable 2.07E-6 0.0681334

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
Acetylursolic acid
Acetyl ursolic acid
Ursolic acid acetate
7372-30-7
CHEMBL410525
Urs-12-en-28-oic acid, 3-(acetyloxy)-, (3beta)-
Ursolicacidacetate
O-acetylursolic acid
Uosolic acid acetate
3-Acetylursolic Acid
3-o-acetylursolic acid
3Beta-O-Acetylursolic Acid
MLS000728570
SCHEMBL10951133
MolPort-039-052-417
AC1O5132
BDBM50346610
ZINC17434116
AKOS016036256
NCGC00247636-01
PL009920
SMR000445682
ST24050338
372U307
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
(1S,2R,4AS,6AS,6BR,8AR,10S,12AR,12BR,14BS)-10-(ACETYLOXY)-1,2,6A,6B,9,9,12A-HEPTAMETHYL-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-ICOSAHYDROPICENE-4A-CARBOXYLIC ACID

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Ursolic acid acetate
Ichnocarpus frutescens Leaf 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 POLB Homo sapiens 39.8107 485314
321 glycogen phosphorylase, muscle associated PYGM Oryctolagus cuniculus 131.826 603224
322 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 131000 10.1016/j.ejmech.2011.02.053 21439694
50 RAR-related orphan receptor gamma Rorc Mus musculus 0.3548 2551
87 streptokinase A precursor ska Streptococcus pyogenes M1 GAS 2.828 1902

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
313357628MolPortSource URLSource DetailMolPort-039-052-417Source Record URL
114524225ABI ChemSource URLSource DetailAC1O5132Source Record URL
259518426ZINCSource URLSource DetailZINC17434116Source Record URL
163875168AKos Consulting & SolutionsSource URLSource DetailAKOS016036256Source Record URL
355046654Yuhao ChemicalSource URLSource DetailYH16386Source Record URL
241143911ChemMolSource URLSource Detail99153015Source Record URL
318357863CambridgeChemSource URLSource DetailCB21404Source Record URL
249869322SyntreeSource URLSource DetailST24050338Source Record URL
354330189TargetMolSource URLSource DetailT3819Source Record URL
349283363Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0801505Source Record URL
341105973Boc SciencesSource URLSource Detail7372-30-7Source Record URL
274953164ChemFacesSource URLSource DetailCFN97219Source Record URL
341845470OChemSource URLSource Detail15342Source Record URL