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Methyl 5,10-dihydroxy-7-methoxy-1,1,3a-trimethyl-1a,2,3,3a,10c,10d-hexahydro-1H-4-oxacyclobuta[cd]indeno[5,6-a]naphthalene-9-carboxylate
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Naphthohydroquinone
| Canonical Smiles | COC(=O)c1cc(OC)c2c(c1O)c1c(c(c2)O)O[C@@]2([C@@H]3[C@H]1C([C@@H]3CC2)(C)C)C |
|---|---|
| InChI | InChI=1S/C23H26O6/c1-22(2)12-6-7-23(3)17(12)18(22)16-15-10(8-13(24)20(16)29-23)14(27-4)9-11(19(15)25)21(26)28-5/h8-9,12,17-18,24-25H,6-7H2,1-5H3/t12-,17+,18+,23+/m1/s1 |
| InChIKey | TVIHKWWLPPRESU-OWMRGQTCSA-N |
| Formula | C23H26O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 398.46 |
| Rotatable Bonds | 2 |
| TPSA | 85.22 |
| LogP | 4.35 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.52 |
| Exact Mass | 398.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pentas bussei | Rubiaceae | Plantae | 387051 |
| 2 | Pentas bussei | Rubiaceae | Plantae | 387051 |
Showing of synonyms
Methyl 5,10-dihydroxy-7-methoxy-1,1,3a-trimethyl-1a,2,3,3a,10c,10d-hexahydro-1H-4-oxacyclobuta[cd]indeno[5,6-a]naphthalene-9-carboxylate
- Bukuru J, De Kimpe N, et al. (2003). Isolation and structural elucidation of natural products from Pentas bussei K. Krause, Pentas lanceolata (Forsk.) Deflers and Pentas parvifolia Hiern (Rubiaceae). Ph.D. Thesis, University of Ghent, Faculty of Bioscience Engineering, Belgium,2003. [View] [PubMed]
- Bukuru J, Van TN, et al. (2003). New pentacyclic cyclol-type naphthohydroquinone from the roots of Pentas bussei. Tetrahedron,2003,59(31),5905-5908. [View] [PubMed]
Pubchem:
12114951
No compound-protein relationship available.
SMILES: C12C3CC1c4c5c(cccc5)ccc4OC2CC3
Level: 0
Mol. Weight: 398.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.52
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.680
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.230
- Plasma Protein Binding
- 83.5
- 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
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.520
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.460
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.290
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.570
- 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
- -18.530
- Rat (Acute)
- 2.480
- Rat (Chronic Oral)
- 2.780
- Fathead Minnow
- 4.060
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 442.550
- Hydration Free Energy
- -5.580
- Log(D) at pH=7.4
- 5.210
- Log(P)
- 5.89
- Log S
- -6.37
- Log(Vapor Pressure)
- -7.96
- Melting Point
- 230.43
- pKa Acid
- 7.73
- pKa Basic
- 3.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8882 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8882 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8788 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8788 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7263 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7263 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.7255 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.7255 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7122 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7122 |