Englerin B - Compound Card

Englerin B

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Englerin B

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Guaiane Sesquiterpene
Canonical Smiles O=C(O[C@@H]1[C@H]2[C@@H](C)CC[C@@H]2[C@]2(O[C@@]1(C[C@@H]2O)C(C)C)C)/C=C/c1ccccc1
InChI InChI=1S/C24H32O4/c1-15(2)24-14-19(25)23(4,28-24)18-12-10-16(3)21(18)22(24)27-20(26)13-11-17-8-6-5-7-9-17/h5-9,11,13,15-16,18-19,21-22,25H,10,12,14H2,1-4H3/b13-11+/t16-,18-,19-,21-,22+,23+,24-/m0/s1
InChIKey VWHNJBKOOIZSEF-AOIXHVRESA-N
Formula C24H32O4
HBA 4
HBD 1
MW 384.52
Rotatable Bonds 4
TPSA 55.76
LogP 4.22
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 384.23
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: 25194883
Nmrshiftdb2: 70091861

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 384.52 g/mol

Structure

SMILES: C1CCC(C12)CC3CCC2O3

Level: 0

Mol. Weight: 384.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 384.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
83.63
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.76
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.56
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.86
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
Toxic
T. Pyriformis
-12.03
Rat (Acute)
3.36
Rat (Chronic Oral)
2.11
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
428.34
Hydration Free Energy
-4.33
Log(D) at pH=7.4
4.63
Log(P)
4.45
Log S
-4.99
Log(Vapor Pressure)
-7.48
Melting Point
134.48
pKa Acid
9.14
pKa Basic
5.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7687
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7687
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7685
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7685

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