Select a section from the left sidebar
Helioscopinolide B
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | O=C1O[C@H]2C(=C1C)C=C1[C@@H](C2)[C@]2(C)CC[C@@H](C([C@H]2CC1)(C)C)O |
|---|---|
| InChI | InChI=1S/C20H28O3/c1-11-13-9-12-5-6-16-19(2,3)17(21)7-8-20(16,4)14(12)10-15(13)23-18(11)22/h9,14-17,21H,5-8,10H2,1-4H3/t14-,15-,16-,17+,20+/m1/s1 |
| InChIKey | KZIADLALQLRZIQ-PANQXIRQSA-N |
| Formula | C20H28O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 316.44 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 3.77 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 316.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia helioscopia | Euphorbiaceae | Plantae | 154990 |
Showing of synonyms
Helioscopinolide B
84799-32-6
(3S,4aS,10aR,11aR,11bS)-3-hydroxy-4,4,8,11b-tetramethyl-2,3,4a,5,6,10a,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-9-one
(3S,4aS,10aR,11aR,11bS)-3-hydroxy-4,4,8,11b-tetramethyl-2,3,4a,5,6,10a,11,11a-octahydro-1H-naphtho(2,1-f)(1)benzofuran-9-one
CHEMBL451142
DTXSID401316117
- 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: C1C(=O)OC(C=12)CC3C(=C2)CCC4C3CCCC4
Level: 0
Mol. Weight: 316.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.45
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.91
- Plasma Protein Binding
- 56.61
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.42
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.71
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.69
- 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
- -3.5
- Rat (Acute)
- 1.95
- Rat (Chronic Oral)
- 1.7
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 398.64
- Hydration Free Energy
- -4.41
- Log(D) at pH=7.4
- 3.71
- Log(P)
- 3.97
- Log S
- -4.45
- Log(Vapor Pressure)
- -6.32
- Melting Point
- 146.37
- pKa Acid
- 10.39
- pKa Basic
- 7.57
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8676 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8676 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8290 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8290 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8179 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8179 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7970 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7970 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7938 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7938 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7902 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7902 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7581 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7581 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7423 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7423 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7406 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7406 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7240 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7240 |
| Retinol-binding protein 2 | P06768 | RET2_RAT | Rattus norvegicus | 3 | 0.7174 |
| Retinol-binding protein 2 | P06768 | RET2_RAT | Rattus norvegicus | 3 | 0.7174 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7094 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7094 |