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Euphornin B
- 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](O)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/C31H42O8/c1-18-13-14-30(6,7)26(34)16-25(37-21(4)32)19(2)15-24-27(39-29(35)23-11-9-8-10-12-23)20(3)17-31(24,36)28(18)38-22(5)33/h8-15,18,20,24-28,34,36H,16-17H2,1-7H3/b14-13+,19-15+/t18-,20-,24-,25+,26+,27-,28-,31+/m0/s1 |
| InChIKey | STETZDTWJFKIHV-OWVGVDTNSA-N |
| Formula | C31H42O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 542.67 |
| Rotatable Bonds | 4 |
| TPSA | 119.36 |
| LogP | 4.39 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.58 |
| Exact Mass | 542.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia helioscopia | Euphorbiaceae | Plantae | 154990 |
Showing of synonyms
Euphornin B
((1S,2S,3aR,4S,5S,6E,9R,11R,12E,13aS)-4,11-diacetyloxy-3a,9-dihydroxy-2,5,8,8,12-pentamethyl-2,3,4,5,9,10,11,13a-octahydro-1H-cyclopenta(12)annulen-1-yl) benzoate
(1R,2S,3AS,4R,5S,9S,11R,13as)-4,11-bis(acetyloxy)-3a,9-dihydroxy-2,5,8,8,12-pentamethyl-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,13ah-cyclopenta(12)annulen-1-yl benzoic acid
(1R,2S,3AS,4R,5S,9S,11R,13as)-4,11-bis(acetyloxy)-3a,9-dihydroxy-2,5,8,8,12-pentamethyl-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,13ah-cyclopenta[12]annulen-1-yl benzoic acid
[(1S,2S,3aR,4S,5S,6E,9R,11R,12E,13aS)-4,11-diacetyloxy-3a,9-dihydroxy-2,5,8,8,12-pentamethyl-2,3,4,5,9,10,11,13a-octahydro-1H-cyclopenta[12]annulen-1-yl] benzoate
90052-87-2
CHEMBL463643
- Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC=CCCCCC=C3
Level: 1
Mol. Weight: 542.67 g/mol
SMILES: C1CCC(C12)CCC=CCCCCC=C2
Level: 0
Mol. Weight: 542.67 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 542.67 g/mol
Antitumor
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.71
- Plasma Protein Binding
- 90.65
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 11.94
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.16
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.41
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.91
- 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
- -1027.6
- Rat (Acute)
- 3.8
- Rat (Chronic Oral)
- 2.54
- Fathead Minnow
- 6.23
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 434.17
- Hydration Free Energy
- -2.82
- Log(D) at pH=7.4
- 3.47
- Log(P)
- 5.8
- Log S
- -5.1
- Log(Vapor Pressure)
- -8.79
- Melting Point
- 156.73
- pKa Acid
- 8.73
- pKa Basic
- 3.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8024 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8024 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7386 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7386 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7314 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7314 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7066 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7066 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7003 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7003 |