Ingenol-3,5,20-triacetate - Compound Card

Ingenol-3,5,20-triacetate

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Ingenol-3,5,20-triacetate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC(=O)CC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@@]([C@@H]1CC(=O)O)(O)[C@@H](CC(=O)O)C(=C3)C)C2=O)C
InChI InChI=1S/C25H32O8/c1-11-10-24-12(2)5-17-21(23(17,3)4)14(22(24)32)6-13(7-18(26)27)16(9-20(30)31)25(24,33)15(11)8-19(28)29/h6,10,12,14-17,21,33H,5,7-9H2,1-4H3,(H,26,27)(H,28,29)(H,30,31)/t12-,14+,15+,16-,17-,21+,24+,25-/m1/s1
InChIKey PYEOPUBSVAACES-CINZWWHMSA-N
Formula C25H32O8
HBA 5
HBD 4
MW 460.52
Rotatable Bonds 6
TPSA 149.2
LogP 2.76
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 460.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia peplus Euphorbiaceae Plantae 38846

Showing of synonyms

  • Rizk AM, Hammouda FM, et al. (1985). Biologically active diterpene esters from Euphorbia peplus. Phytochemistry,1985,24(7),1605-1606. [View]
Pubchem: 162817232
Nmrshiftdb2: 70058654
CPRiL: 379589
Structure

SMILES: C1CC(C2)C2C(C3=O)C=CCC(C134)CC=C4

Level: 0

Mol. Weight: 460.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.09
Plasma Protein Binding
79.34
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-1.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.34
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.48
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-63.85
Rat (Acute)
2.15
Rat (Chronic Oral)
2.58
Fathead Minnow
3.48
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
488.83
Hydration Free Energy
-2.62
Log(D) at pH=7.4
-3.54
Log(P)
2.54
Log S
-2.56
Log(Vapor Pressure)
-16.31
Melting Point
264.11
pKa Acid
5.81
pKa Basic
6.23

No predicted protein targets found for this compound.

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