Beta-amyrin acetate - Compound Card

Beta-amyrin acetate

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Beta-amyrin acetate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)OC1CCC2(C(C1(C)C)CCC1(C2CC=C2C1(C)CCC1(C2CC(C)(C)CC1)C)C)C
InChI InChI=1S/C32H52O2/c1-21(33)34-26-13-14-30(7)24(28(26,4)5)12-15-32(9)25(30)11-10-22-23-20-27(2,3)16-17-29(23,6)18-19-31(22,32)8/h10,23-26H,11-20H2,1-9H3
InChIKey UMRPOGLIBDXFNK-UHFFFAOYSA-N
Formula C32H52O2
HBA 2
HBD 0
MW 468.77
Rotatable Bonds 1
TPSA 26.3
LogP 8.74
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 Commiphora kua Burseraceae Plantae 246356
2 Commiphora confusa Burseraceae Plantae 43868
3 Vernonia auriculifera Asteraceae Plantae 3032568
4 Vernonia auriculifera Asteraceae Plantae 3032568

Showing of synonyms

  • Manguro LO, Ugi I, et al. (2003). Dammarane triterpenes of Commiphora confusa resin. Chemical and Pharmaceutical Bulletin,2003,51(5),483-486. [View] [PubMed]
  • Manguro LO, Ugi I, et al. (2003). Further bisabolenes and dammarane triterpenes of Commiphora kua resin.. Chemical and Pharmaceutical Bulletin,2003,51(5),479-482. [View] [PubMed]
  • 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]
Pubchem: 345510
Nmrshiftdb2: 60021662
CPRiL: 146434
Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 468.77 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.01
Plasma Protein Binding
39.32
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
6.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.83
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.36
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.72
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-110.82
Rat (Acute)
2.03
Rat (Chronic Oral)
1.35
Fathead Minnow
5.04
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
441.6
Hydration Free Energy
-2.66
Log(D) at pH=7.4
7.51
Log(P)
9.12
Log S
-7.55
Log(Vapor Pressure)
-7.06
Melting Point
212.34
pKa Acid
12.75
pKa Basic
7.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8207
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8207
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8067
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7805
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7805
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7555
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7555
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7554
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7554
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7495
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7495
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7432
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7432
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7311
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7311
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7214
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7214
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7181
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7181
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7146
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7146

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