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Ingenol-20-O-octanoate
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | [O-]C(=O)CCCCCCCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H](C3([C@@]([C@@H]1O)(O)[C@@H](O)C(=C3)C)C2=O)C |
|---|---|
| InChI | InChI=1S/C27H40O6/c1-15-14-26-16(2)12-19-21(25(19,3)4)18(24(26)32)13-17(23(31)27(26,33)22(15)30)10-8-6-5-7-9-11-20(28)29/h13-14,16,18-19,21-23,30-31,33H,5-12H2,1-4H3,(H,28,29)/p-1/t16-,18+,19-,21+,22+,23-,26?,27-/m1/s1 |
| InChIKey | RLRYPFZIWXJLKS-VTTQBEPZSA-M |
| Formula | C27H39O6- |
| HBA | 6 |
| HBD | 3 |
| MW | 459.6 |
| Rotatable Bonds | 8 |
| TPSA | 117.89 |
| LogP | 2.3 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | -1 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 459.28 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia peplus | Euphorbiaceae | Plantae | 38846 |
Showing of synonyms
Ingenol-20-O-octanoate
- Rizk AM, Hammouda FM, et al. (1985). Biologically active diterpene esters from Euphorbia peplus. Phytochemistry,1985,24(7),1605-1606. [View]
No compound-protein relationship available.
SMILES: C1CC(C2)C2C(C3=O)C=CCC(C134)CC=C4
Level: 0
Mol. Weight: 459.6 g/mol
Pro-inflammatory
Absorption
- Caco-2 (logPapp)
- -5.57
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.11
- Plasma Protein Binding
- 89.25
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.89
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.74
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.48
- Micronucleos
- Safe
- 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
- -98.13
- Rat (Acute)
- 2.63
- Rat (Chronic Oral)
- 2.89
- Fathead Minnow
- 4.03
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 462.61
- Hydration Free Energy
- -2.91
- Log(D) at pH=7.4
- 2.1
- Log(P)
- 4.03
- Log S
- -3.88
- Log(Vapor Pressure)
- -11.37
- Melting Point
- 167.47
- pKa Acid
- 3.79
- pKa Basic
- 6.2
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.8039 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.8039 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7934 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7934 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7925 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7925 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7672 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7672 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.7481 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.7481 |
| Bile salt hydrolase/transferase | P54965 | CBH_CLOPE | Clostridium perfringens | 3 | 0.7207 |
| Bile salt hydrolase/transferase | P54965 | CBH_CLOPE | Clostridium perfringens | 3 | 0.7207 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7158 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7158 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7102 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7102 |