3-O-acetyl-ursolic acid - Compound Card

3-O-acetyl-ursolic acid

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3-O-acetyl-ursolic acid

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpene
Canonical Smiles CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC(=O)C)C)C)C2C1C)C)C(=O)O
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)
InChIKey PHFUCJXOLZAQNH-UHFFFAOYSA-N
Formula C32H50O4
HBA 3
HBD 1
MW 498.75
Rotatable Bonds 2
TPSA 63.6
LogP 7.66
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 498.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Alchornea laxiflora Euphorbiaceae Plantae 316698

Showing of synonyms

  • Siwe-Noundou X, Ndinteh D, et al. (2019). Biological activity of plant extracts and isolated compounds from Alchornea laxiflora: Anti-HIV, antibacterial and cytotoxicity evaluation. South African Journal of Botany, 2019, 122, 498-503. [View]
Pubchem: 619164
Nmrshiftdb2: 60025720
CPRiL: 406650
Structure

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

Level: 0

Mol. Weight: 498.75 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.89
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.21
Plasma Protein Binding
30.57
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
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.67
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.77
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-336.26
Rat (Acute)
2.26
Rat (Chronic Oral)
1.78
Fathead Minnow
4.69
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
464.71
Hydration Free Energy
-2.79
Log(D) at pH=7.4
5.21
Log(P)
7.74
Log S
-6.64
Log(Vapor Pressure)
-8.64
Melting Point
230.66
pKa Acid
7.14
pKa Basic
8.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8297
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8280
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7607
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7368

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