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Madeleinol A
- Family: Plantae - Hypericaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | CC(C(=O)c1c(O)cc(c2c1O[C@]1(C)CC[C@H](C([C@H]1C2)(C)C)O)O)C |
|---|---|
| InChI | InChI=1S/C20H28O5/c1-10(2)17(24)16-13(22)9-12(21)11-8-14-19(3,4)15(23)6-7-20(14,5)25-18(11)16/h9-10,14-15,21-23H,6-8H2,1-5H3/t14-,15-,20-/m1/s1 |
| InChIKey | WFCVPAAKDWTYNQ-STXHMFSFSA-N |
| Formula | C20H28O5 |
| HBA | 5 |
| HBD | 3 |
| MW | 348.44 |
| Rotatable Bonds | 2 |
| TPSA | 86.99 |
| LogP | 3.43 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 348.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hypericum roeperianum | Hypericaceae | Plantae | — |
Showing of synonyms
Madeleinol A
CHEMBL3613750
1-[(7R,8aR,10aR)-1,3,7-trihydroxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-4-yl]-2-methyl-propan-1-one
No compound-protein relationship available.
SMILES: c1cccc(c12)OC3C(C2)CCCC3
Level: 0
Mol. Weight: 348.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.88
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.81
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.72
- Plasma Protein Binding
- 75.88
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- 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
- 14.83
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.48
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.95
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.12
- 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
- Toxic
- T. Pyriformis
- 0.43
- Rat (Acute)
- 2.45
- Rat (Chronic Oral)
- 2.16
- Fathead Minnow
- 4.01
- 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
- 394.4
- Hydration Free Energy
- -9.45
- Log(D) at pH=7.4
- 3.12
- Log(P)
- 4.3
- Log S
- -4.4
- Log(Vapor Pressure)
- -7.31
- Melting Point
- 179.48
- pKa Acid
- 7.49
- pKa Basic
- 5.24
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8562 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.8025 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7782 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7766 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7552 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7438 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7360 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7167 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7122 |
| Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7079 |
| Thymidine phosphorylase | P07650 | TYPH_ECOLI | Escherichia coli | 4 | 0.7075 |
| orotidine-5'-phosphate decarboxylase | Q8T6J6 | Q8T6J6_PLAFA | Plasmodium falciparum | 4 | 0.7001 |