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Euphornin
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | CC(=O)O[C@H]1[C@@H](C)/C=C\C(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 |
|---|---|
| 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/h9-16,19,21,26-30,38H,17-18H2,1-8H3/b15-14-,20-16-/t19-,21-,26-,27+,28+,29-,30-,33+/m0/s1 |
| InChIKey | BRVXVMOWTHQKHC-NHTJSLHDSA-N |
| Formula | C33H44O9 |
| HBA | 9 |
| HBD | 1 |
| MW | 584.71 |
| Rotatable Bonds | 5 |
| TPSA | 125.43 |
| LogP | 4.96 |
| 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 | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia helioscopia | Euphorbiaceae | Plantae | 154990 |
Showing of synonyms
Euphornin
80454-47-3
[(1S,2S,3aR,4S,5S,6Z,9R,11R,12Z,13aS)-4,9,11-triacetyloxy-3a-hydroxy-2,5,8,8,12-pentamethyl-2,3,4,5,9,10,11,13a-octahydro-1H-cyclopenta[12]annulen-1-yl] benzoate
[(1R,2S,3S,4Z,7R,9R,10Z,12S,13S,14S)-2,7,9-triacetyloxy-1-hydroxy-3,6,6,10,14-pentamethyl-13-bicyclo[10.3.0]pentadeca-4,10-dienyl] benzoate
DA-53070
3aH-Cyclopentacyclododecene-1,3a,4,9,11-pentol, 1,2,3,4,5,8,9,10,11,13a-decahydro-2,5,8,8,12-pentamethyl-, 4,9,11-triacetate 1-benzoate, (1S,2S,3aR,4S,5S,6E,9R,11R,12E,13aS)-
3aH-Cyclopentacyclododecene-1,3a,4,9,11-pentol, 1,2,3,4,5,8,9,10,11,13a-decahydro-2,5,8,8,12-pentamethyl-, 4,9,11-triacetate 1-benzoate, (1S-(1R*,2R*,3aS*,4R*,5R*,6E,9S*,11S*,12E,13aR*))-
- Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
CPRiL:
135813
SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC=CCCCCC=C3
Level: 1
Mol. Weight: 584.71 g/mol
SMILES: C1CCC(C12)CCC=CCCCCC=C2
Level: 0
Mol. Weight: 584.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 584.71 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.69
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.67
- Plasma Protein Binding
- 93.9
- 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
- 11.84
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.28
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.61
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.25
- 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
- -3807.54
- Rat (Acute)
- 3.59
- Rat (Chronic Oral)
- 2.44
- Fathead Minnow
- 15.23
- 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
- 400.27
- Hydration Free Energy
- -2.88
- Log(D) at pH=7.4
- 3.62
- Log(P)
- 5.91
- Log S
- -5.54
- Log(Vapor Pressure)
- -9.19
- Melting Point
- 133.1
- pKa Acid
- 9.88
- pKa Basic
- 2.99
| 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 | 0.8865 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8865 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8858 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8858 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7909 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7909 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7861 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7861 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7720 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7720 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7285 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7285 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7099 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7099 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7060 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7060 |