Lupeol acetate - Compound Card

Lupeol acetate

Select a section from the left sidebar

Lupeol acetate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C)C)C
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
InChIKey ODSSDTBFHAYYMD-YOJQYFTNSA-N
Formula C32H52O2
HBA 2
HBD 0
MW 468.77
Rotatable Bonds 2
TPSA 26.3
LogP 8.6
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 468.4
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Torilis radiata Apiaceae Plantae 40890
2 Francoeuria crispa Asteraceae Plantae 1548540
3 Lactuca sativa Asteraceae Plantae 4236
4 Pulicaria undulata Asteraceae Plantae 119186
5 Sonchus macrocarpus Asteraceae Plantae 2984305
6 Garcinia edulis Clusiaceae-Guttiferae Plantae 58227
7 Escinops ellenbeckii Asteraceae Plantae —
8 Vernonia auriculifera Asteraceae Plantae 3032568
9 Vernonia auriculifera Asteraceae Plantae 3032568

Showing of synonyms

  • Magadula JJ. (2010). A bioactive isoprenylated xanthone and other constituents of Garcinia edulis. Fitoterapia,2010,81(5),420-423. [View] [PubMed]
  • Metwally M, Dawidar AA, et al. (1986). A new thymol derivative from Pulicaria undulata. Chemical and Pharmaceutical Bulletin,1986,34(1),378-379. [View]
  • Hymete A, Rohloff J, et al. (2005). Acetylenic thiophenes from the roots of Escinops ellenbeckii from Ethiopia. Natural Product Research,2005,19(8),755-761. [View] [PubMed]
  • Ezzat SM, Abdallah HM, et al. (2012). Hepatoprotective constituents of Torilis radiata Moench (Apiaceae). Natural Product Research,2012,26(3),282-285. [View] [PubMed]
  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
  • Mahmoud ZF, Kassem FF, et al. (1986). Sesquiterpene lactones from Lactuca sativa. Phytochemistry,1986,25(3),141-748. [View]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA, et al. (2011). Triterpenoids from Vernonia auriculifera Hiern exhibit antimicrobial activity. African Journal of Pharmacy and Pharmacology,2011,5(8),1150-1156. [View] [PubMed]
  • Mahmoud Z, El-Masry S, et al. (1983). Two eudesmanolides from Sonchus macrocarpus. Phytochemistry,1983,22(5),1290-1291. [View]
Pubchem: 92157
Kegg Ligand: C08630
Chebi: 69744
Nmrshiftdb2: 60018578
Metabolights: MTBLC69744
CPRiL: 239957
Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 468.77 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.01
Plasma Protein Binding
92.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.88
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.65
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.58
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-157.2
Rat (Acute)
2.03
Rat (Chronic Oral)
1.49
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
465.14
Hydration Free Energy
-2.78
Log(D) at pH=7.4
7.73
Log(P)
8.82
Log S
-7.46
Log(Vapor Pressure)
-8.13
Melting Point
199.8
pKa Acid
12.93
pKa Basic
7.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7872
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7872
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7853
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7853
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7130
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7083
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7083

Download SDF