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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)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)CC1C2[C@@H](C(C1=O)(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C)C
InChI InChI=1S/C39H48O16/c1-18-15-38(48)28(29(18)54-33(47)24-13-11-10-12-14-24)32(53-26(45)17-49-19(2)40)39(55-23(6)44)16-25-27(31(50-20(3)41)36(7,8)30(25)46)37(9,34(38)51-21(4)42)35(39)52-22(5)43/h10-14,18,25,27-29,31-32,34-35,48H,15-17H2,1-9H3/t18-,25?,27?,28+,29-,31-,32+,34+,35-,37+,38+,39+/m0/s1
InChIKey IFVZGQVJBOEHFG-AJICLSQGSA-N
Formula C39H48O16
HBA 16
HBD 1
MW 772.8
Rotatable Bonds 9
TPSA 221.4
LogP 2.44
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 55
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 772.29
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: 163032699

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 772.8 g/mol

Structure

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

Level: 0

Mol. Weight: 772.8 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 772.8 g/mol

Anti-feedant
Molluscicidal

Absorption

Caco-2 (logPapp)
-5.38
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
2.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1010.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.21
Plasma Protein Binding
94.98
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
7.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-25.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.92
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
-1839702.09
Rat (Acute)
4.1
Rat (Chronic Oral)
3.15
Fathead Minnow
2327.89
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
201652.75
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.68
Log(P)
3.45
Log S
-4.52
Log(Vapor Pressure)
-6623.5
Melting Point
213.39
pKa Acid
-21.38
pKa Basic
-2.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8464
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8464
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8025
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8025
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7978
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7978
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7225
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7225
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7211
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7211
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7188
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7188
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7075
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7075

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