3,11-dioxoolean-12-en-28-oic acid - Compound Card

3,11-dioxoolean-12-en-28-oic acid

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3,11-dioxoolean-12-en-28-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C1C=C2[C@H]3CC(C)(C)CC[C@@]3(CC[C@]2([C@]2([C@H]1[C@@]1(C)CCC(=O)C(C1CC2)(C)C)C)C)C(=O)O
InChI InChI=1S/C30H44O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)17-25)16-20(31)23-27(5)10-9-22(32)26(3,4)21(27)8-11-29(23,28)7/h16,19,21,23H,8-15,17H2,1-7H3,(H,33,34)/t19-,21?,23-,27+,28-,29-,30+/m1/s1
InChIKey VDDPQVQCXWFZJM-LDLRJHFFSA-N
Formula C30H44O4
HBA 3
HBD 1
MW 468.68
Rotatable Bonds 1
TPSA 71.44
LogP 6.62
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 468.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ekebergia capensis Meliaceae Plantae 124949

Showing of synonyms

  • Murata T, Miyase T, et al. (2008). Antiplasmodial triterpenoids from Ekebergia capensis.. Journal of Natural Products,2008,71(2),167-174. [View] [PubMed]
Pubchem: 91367949

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(C(=O)C3)C5C(CC4)CC(=O)CC5

Level: 0

Mol. Weight: 468.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.690
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.160
Plasma Protein Binding
95.18
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
3.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.480
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.700
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
Toxic
T. Pyriformis
-111.800
Rat (Acute)
2.270
Rat (Chronic Oral)
2.210
Fathead Minnow
3.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
502.970
Hydration Free Energy
-2.590
Log(D) at pH=7.4
4.110
Log(P)
5.19
Log S
-5.74
Log(Vapor Pressure)
-8.79
Melting Point
286.26
pKa Acid
5.2
pKa Basic
6.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7606
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7606
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7060
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7060

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