(2S,3S,4R,5R,6R,8R,12S,13S,14R,15R)-1,5,8,14-tetraacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-paraliane - Compound Card

(2S,3S,4R,5R,6R,8R,12S,13S,14R,15R)-1,5,8,14-tetraacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-paraliane

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(2S,3S,4R,5R,6R,8R,12S,13S,14R,15R)-1,5,8,14-tetraacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-paraliane

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)O[C@@H]1[C@H](C)[C@@H]([C@H]2[C@@]1(O)C(OC(=O)C)[C@@]1([C@@]([C@@H]2OC(=O)C)(C)C[C@@]2([C@H]1CC(C2=O)(C)C)OC(=O)C)C)OC(=O)c1ccccc1
InChI InChI=1S/C35H44O12/c1-17-25(46-28(40)22-13-11-10-12-14-22)24-27(44-19(3)37)32(8)16-34(47-21(5)39)23(15-31(6,7)29(34)41)33(32,9)30(45-20(4)38)35(24,42)26(17)43-18(2)36/h10-14,17,23-27,30,42H,15-16H2,1-9H3/t17-,23+,24-,25+,26-,27-,30?,32+,33-,34+,35+/m1/s1
InChIKey SJGCQOVOMXNEOA-ZJNYLYGOSA-N
Formula C35H44O12
HBA 12
HBD 1
MW 656.73
Rotatable Bonds 6
TPSA 168.8
LogP 3.35
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 656.28
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia paralias Euphorbiaceae Plantae 756629

Showing of synonyms

  • Abdelgaleil SAM, El-Aswad AF, et al. (2002). Molluscicidal and anti-feedant activities of diterpenes from Euphorbia paralias L. Pest Management,2002,58,479-482. [View] [PubMed]
Pubchem: 162999878

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CCC(C3)C2CC(C4)C3C(C45)CCC5=O

Level: 1

Mol. Weight: 656.73 g/mol

Structure

SMILES: O=C1CCC(C12)C3C(C2)CC4C(C3)CCC4

Level: 0

Mol. Weight: 656.73 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 656.73 g/mol

Anti-feedant
Molluscicidal

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
23.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.36
Plasma Protein Binding
100.81
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
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
8.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.94
Micronucleos
Toxic
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
Safe
T. Pyriformis
-47562.0
Rat (Acute)
4.55
Rat (Chronic Oral)
3.0
Fathead Minnow
79.62
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
1074.06
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.38
Log(P)
4.04
Log S
-5.09
Log(Vapor Pressure)
-56.89
Melting Point
228.39
pKa Acid
7.32
pKa Basic
-0.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7044
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7044

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