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Voucapane
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Furanoditerpenoid
| Canonical Smiles | C[C@@H]1[C@@H]2CC[C@@H]3[C@]([C@H]2Cc2c1cco2)(C)CCCC3(C)C |
|---|---|
| InChI | InChI=1S/C20H30O/c1-13-14-6-7-18-19(2,3)9-5-10-20(18,4)16(14)12-17-15(13)8-11-21-17/h8,11,13-14,16,18H,5-7,9-10,12H2,1-4H3/t13-,14+,16+,18+,20-/m1/s1 |
| InChIKey | IKJJQJVKGWMIBD-WNEFFWMYSA-N |
| Formula | C20H30O |
| HBA | 1 |
| HBD | 0 |
| MW | 286.46 |
| Rotatable Bonds | 0 |
| TPSA | 13.14 |
| LogP | 5.8 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 286.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Stuhlmannia moavi | Caesalpiniaceae | Plantae | 191956 |
| 2 | Caesalpinia volkensii | Leguminosae/Fabaceae | Plantae | 1387603 |
Showing of synonyms
Voucapane
- Ochieng' CO, Owuor PO, et al. (2012). Antinociceptive and antiplasmodial activities of cassane furanoditerpenes from Caesalpinia volkensii H. root bark.. Fitoterapia,2012,83(1),74-80. [View] [PubMed]
- Odalo JO, Joseph CC, et al. (2009). Cytotoxic, anti-proliferative and antimicrobial furanoditerpenoids from Stuhlmania moavi. Phytochemistry,2009,70(17-18),2047-2052. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4
Level: 0
Mol. Weight: 286.46 g/mol
Anti-proliferative
Antibacterial
Antifungal
Antinociceptive
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.67
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.46
- Plasma Protein Binding
- 77.64
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.2
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.71
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.48
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.12
- Micronucleos
- Safe
- 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
- 1.47
- Rat (Acute)
- 1.97
- Rat (Chronic Oral)
- 2.03
- Fathead Minnow
- 3.97
- 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
- 345.61
- Hydration Free Energy
- -1.48
- Log(D) at pH=7.4
- 5.45
- Log(P)
- 6.23
- Log S
- -5.66
- Log(Vapor Pressure)
- -5.62
- Melting Point
- 112.99
- pKa Acid
- 12.02
- pKa Basic
- 7.82
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7610 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7610 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7572 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7572 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7560 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7560 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7359 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7359 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7245 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7245 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7232 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7232 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7210 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7210 |
| Retinoic acid receptor RXR | Q8T5C6 | RXR_BIOGL | Biomphalaria glabrata | 3 | 0.7199 |
| Retinoic acid receptor RXR | Q8T5C6 | RXR_BIOGL | Biomphalaria glabrata | 3 | 0.7199 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 2 | 0.7172 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 2 | 0.7172 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7142 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7142 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7044 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7044 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7037 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7037 |