5,11-jatrophadiene-3-benzoyloxy-7,9,14-triacetyloxy-15-ol - Compound Card

5,11-jatrophadiene-3-benzoyloxy-7,9,14-triacetyloxy-15-ol

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5,11-jatrophadiene-3-benzoyloxy-7,9,14-triacetyloxy-15-ol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OC1/C(=C/CC(C)(C)[C@H](OC(=O)C)C[C@H](/C(=C/[C@@H]2[C@]1(O)C[C@H]([C@@H]2OC(=O)c1ccccc1)C)/C)OC(=O)C)/C
InChI InChI=1S/C33H44O9/c1-19-14-15-32(7,8)28(40-23(5)35)17-27(39-22(4)34)20(2)16-26-29(42-31(37)25-12-10-9-11-13-25)21(3)18-33(26,38)30(19)41-24(6)36/h9-14,16,21,26-30,38H,15,17-18H2,1-8H3/b19-14+,20-16+/t21-,26+,27-,28-,29+,30?,33-/m1/s1
InChIKey GLGJKTPMFLAWOO-PKIVIFHDSA-N
Formula C33H44O9
HBA 9
HBD 1
MW 584.71
Rotatable Bonds 5
TPSA 125.43
LogP 5.11
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 584.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia helioscopia Euphorbiaceae Plantae 154990

Showing of synonyms

  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem: 162817271

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CCC(C23)CC=CCCCCCC=C3

Level: 1

Mol. Weight: 584.71 g/mol

Structure

SMILES: C1CCC(C12)CC=CCCCCCC=C2

Level: 0

Mol. Weight: 584.71 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 584.71 g/mol

Vasodepressor

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
94.96
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
10.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.38
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.09
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
-3805.75
Rat (Acute)
3.48
Rat (Chronic Oral)
2.41
Fathead Minnow
16.35
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
404.28
Hydration Free Energy
-2.89
Log(D) at pH=7.4
3.66
Log(P)
6.37
Log S
-5.59
Log(Vapor Pressure)
-8.75
Melting Point
148.68
pKa Acid
9.37
pKa Basic
3.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8415
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8415
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7121
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7121
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7068
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7068

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