Englerin A - Compound Card

Englerin A

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Englerin A

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Guaiane Sesquiterpene
Canonical Smiles OCC(=O)O[C@@H]1C[C@@]2(O[C@@]1(C)[C@@H]1CC[C@H]([C@H]1[C@@H]2OC(=O)/C=C/c1ccccc1)C)C(C)C
InChI InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1
InChIKey GACOFEKSDCOVMV-RRYXBOBMSA-N
Formula C26H34O6
HBA 6
HBD 1
MW 442.55
Rotatable Bonds 6
TPSA 82.06
LogP 3.77
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 442.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Phyllanthus engleri Euphorbiaceae Plantae 1899179

Showing of synonyms

  • Ratnayake R, Covell D, et al. (2009). Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.. Organic Letters,2009,11(1),57-60. [View] [PubMed]
Pubchem: 46242512
Chebi: 72441
Nmrshiftdb2: 70091860
Metabolights: MTBLC72441
CPRiL: 88596
Structure

SMILES: O1C2CCC1C(C(C23)CCC3)OC(=O)C=Cc4ccccc4

Level: 1

Mol. Weight: 442.55 g/mol

Structure

SMILES: C1CCC(C12)CC3CCC2O3

Level: 0

Mol. Weight: 442.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 442.55 g/mol

Renal cancer cell growth inhibition

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
86.15
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
11.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.69
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.34
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
-90.71
Rat (Acute)
2.92
Rat (Chronic Oral)
2.39
Fathead Minnow
4.02
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
444.36
Hydration Free Energy
-2.37
Log(D) at pH=7.4
4.2
Log(P)
4.32
Log S
-5.04
Log(Vapor Pressure)
-8.33
Melting Point
145.9
pKa Acid
9.25
pKa Basic
4.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7660
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7660
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7630
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7630
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7440
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7440
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7294
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7294

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