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

(2S,3S,4R,5R,6R,8R,11S,12S,13R,14R, 15R)-6,14,17-triacetoxy-5-(2-hydroxyacetoxy)-3-benzoyloxy-15-hydroxy-9-oxo-segetane

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(2S,3S,4R,5R,6R,8R,11S,12S,13R,14R, 15R)-6,14,17-triacetoxy-5-(2-hydroxyacetoxy)-3-benzoyloxy-15-hydroxy-9-oxo-segetane

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OCC(=O)O[C@@H]1[C@H]2[C@@H](OC(=O)c3ccccc3)[C@H](C[C@]2(O)[C@@H]([C@@]2([C@@H]([C@@]1(OC(=O)C)CC1C2CC(C1=O)(C)C)OC(=O)C)C)OC(=O)C)C
InChI InChI=1S/C35H44O13/c1-17-13-34(43)25(26(17)47-29(42)21-11-9-8-10-12-21)28(46-24(40)16-36)35(48-20(4)39)14-22-23(15-32(5,6)27(22)41)33(7,30(34)44-18(2)37)31(35)45-19(3)38/h8-12,17,22-23,25-26,28,30-31,36,43H,13-16H2,1-7H3/t17-,22?,23?,25+,26-,28+,30+,31-,33+,34+,35+/m0/s1
InChIKey XIZUZZXWYLTRAC-IOLKFXSUSA-N
Formula C35H44O13
HBA 13
HBD 2
MW 672.72
Rotatable Bonds 7
TPSA 189.03
LogP 2.32
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 672.28
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: 162959225

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 672.72 g/mol

Structure

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

Level: 0

Mol. Weight: 672.72 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 672.72 g/mol

Anti-feedant
Molluscicidal

Absorption

Caco-2 (logPapp)
-5.43
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
47.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
94.47
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
6.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.04
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
-91026.83
Rat (Acute)
4.27
Rat (Chronic Oral)
3.15
Fathead Minnow
129.26
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
4996.29
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.07
Log(P)
3.02
Log S
-4.12
Log(Vapor Pressure)
-200.75
Melting Point
216.83
pKa Acid
5.8
pKa Basic
0.26
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 0.8369
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8369
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8366
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8366
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7826
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7826
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7250
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7250
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7107
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7107

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