Ekeberin A - Compound Card

Ekeberin A

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Ekeberin A

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC([C@@]12CC[C@@]3(CO1)[C@@H](O2)[C@H]1CC[C@H]2[C@@]([C@@]1(CC3)C)(C)CC[C@@H]1[C@]2(C)CCC(=O)C1(C)C)C
InChI InChI=1S/C30H48O3/c1-19(2)30-17-16-29(18-32-30)15-14-27(6)20(24(29)33-30)8-9-22-26(5)12-11-23(31)25(3,4)21(26)10-13-28(22,27)7/h19-22,24H,8-18H2,1-7H3/t20-,21+,22-,24+,26+,27-,28-,29+,30+/m1/s1
InChIKey KPGLSDWWUAAHSQ-VDLWMDHTSA-N
Formula C30H48O3
HBA 3
HBD 0
MW 456.71
Rotatable Bonds 1
TPSA 35.53
LogP 7.17
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.97
Exact Mass 456.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ekebergia capensis Meliaceae Plantae 124949
2 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]
  • Irungu BN, Orwa JA, et al. (2014). Constituents of the roots and leaves of Ekebergia capensis and their potential antiplasmodial and cytotoxic activities.. Molecules,2014,19(9),14235-14246. [View] [PubMed]
Pubchem: 101843374
Nmrshiftdb2: 60114459

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)CC(CC2)C1C(CC3)C2C(CC4)C3C(C456)OC(CC5)OC6

Level: 0

Mol. Weight: 456.71 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.85
Plasma Protein Binding
82.76
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
15.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.28
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
Toxic
T. Pyriformis
-139.74
Rat (Acute)
2.0
Rat (Chronic Oral)
1.2
Fathead Minnow
3.81
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
460.04
Hydration Free Energy
-2.77
Log(D) at pH=7.4
6.11
Log(P)
6.52
Log S
-6.92
Log(Vapor Pressure)
-8.53
Melting Point
202.87
pKa Acid
11.01
pKa Basic
7.22
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 0.8672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8672
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8601
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7579
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7579

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