(2S,3S,4R,5R,6R,11S,13R,14S, 15R,17R)-5,6,11,14,17-pentaacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-seget-8(12)-ene - Compound Card

(2S,3S,4R,5R,6R,11S,13R,14S, 15R,17R)-5,6,11,14,17-pentaacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-seget-8(12)-ene

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(2S,3S,4R,5R,6R,11S,13R,14S, 15R,17R)-5,6,11,14,17-pentaacetoxy-3-benzoyloxy-15-hydroxy-9-oxo-seget-8(12)-ene

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)O[C@@H]1[C@H]2[C@@H](OC(=O)c3ccccc3)[C@H](C[C@]2(O)[C@@H]([C@@]2(C([C@@]1(OC(=O)C)CC1=C2[C@@H](C(C1=O)(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C)C
InChI InChI=1S/C37H44O14/c1-17-15-36(45)26(27(17)50-31(44)23-13-11-10-12-14-23)30(47-19(3)39)37(51-22(6)42)16-24-25(29(46-18(2)38)34(7,8)28(24)43)35(9,32(36)48-20(4)40)33(37)49-21(5)41/h10-14,17,26-27,29-30,32-33,45H,15-16H2,1-9H3/t17-,26+,27-,29-,30+,32+,33?,35+,36+,37+/m0/s1
InChIKey SWSXELQHTSGROU-XZOGGQITSA-N
Formula C37H44O14
HBA 14
HBD 1
MW 712.75
Rotatable Bonds 7
TPSA 195.1
LogP 2.96
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 712.27
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: 163015199
Nmrshiftdb2: 70084378

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CCC(C3)C2CC(C4)CC3C(=C45)CCC5=O

Level: 1

Mol. Weight: 350.46 g/mol

Structure

SMILES: O=C1CCC(=C12)C3CC(C2)CC4C(C3)CCC4

Level: 0

Mol. Weight: 230.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anti-feedant
Molluscicidal

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
157.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
95.4
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.27
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.37
Micronucleos
Toxic
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
-292235.59
Rat (Acute)
4.28
Rat (Chronic Oral)
3.25
Fathead Minnow
382.17
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
26774.38
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.93
Log(P)
3.19
Log S
-4.34
Log(Vapor Pressure)
-924.08
Melting Point
216.29
pKa Acid
4.57
pKa Basic
-1.63
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 0.8150
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8150

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