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2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro-1,4,5-trioxaphenanthren-6-one
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | CO[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)ccc1c2oc(=O)cc1 |
|---|---|
| InChI | InChI=1S/C20H18O8/c1-23-13-8-11(9-14(24-2)16(13)22)18-20(25-3)28-19-12(26-18)6-4-10-5-7-15(21)27-17(10)19/h4-9,18,20,22H,1-3H3/t18-,20+/m1/s1 |
| InChIKey | DXBMMMITVSFLLA-QUCCMNQESA-N |
| Formula | C20H18O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 386.36 |
| Rotatable Bonds | 4 |
| TPSA | 96.59 |
| LogP | 3.0 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 386.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Afraegle paniculata | Rutaceae | Plantae | 231460 |
Showing of synonyms
2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro-1,4,5-trioxaphenanthren-6-one
Pubchem:
162967806
Zinc:
ZINC000238741420
No compound-protein relationship available.
SMILES: O=c(o1)ccc2ccc(c3c12)OC(CO3)c4ccccc4
Level: 1
Mol. Weight: 386.36 g/mol
SMILES: O1CCOc(c1c23)ccc2ccc(=O)o3
Level: 0
Mol. Weight: 386.36 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 386.36 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.610
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.87
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.570
- Plasma Protein Binding
- 86.45
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.400
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.600
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.290
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.880
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -12.080
- Rat (Acute)
- 2.400
- Rat (Chronic Oral)
- 1.940
- Fathead Minnow
- 4.960
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 462.890
- Hydration Free Energy
- -7.240
- Log(D) at pH=7.4
- 2.230
- Log(P)
- 1.95
- Log S
- -3.96
- Log(Vapor Pressure)
- -8.28
- Melting Point
- 180.51
- pKa Acid
- 7.32
- pKa Basic
- -0.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8558 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7604 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 2 | 0.7460 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.6812 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.6689 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.6317 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.6191 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.6141 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.5601 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 2 | 0.5466 |
| Metallo-beta-lactamase type 2 | P25910 | BLAB_BACFG | Bacteroides fragilis | 3 | 0.5341 |
| Flavodoxin | P00323 | FLAV_DESVH | Nitratidesulfovibrio vulgaris | 5 | 0.5026 |
| Cell division control protein 42 homolog | P60953 | CDC42_HUMAN | Homo sapiens | 3 | 0.5007 |