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Xanthoxyletin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | COc1c2C=CC(Oc2cc2c1ccc(=O)o2)(C)C |
|---|---|
| InChI | InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3 |
| InChIKey | JSJIIHRNDMLJGK-UHFFFAOYSA-N |
| Formula | C15H14O4 |
| HBA | 4 |
| HBD | 0 |
| MW | 258.27 |
| Rotatable Bonds | 1 |
| TPSA | 48.67 |
| LogP | 2.99 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 258.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Afraegle paniculata | Rutaceae | Plantae | 231460 |
| 2 | Clausena anisata | Rutaceae | Plantae | 159034 |
Showing of synonyms
Xanthoxyletin
84-99-1
Xanthoxylin N
Xanthoxyloin
5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
UNII-69MPX4M5VD
69MPX4M5VD
NSC 35542
NSC-35542
XANTHOXYLETIN [MI]
5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
DTXSID70232891
2H,8H-Benzo(1,2-b:5,4-b')dipyran-2-one, 5-methoxy-8,8-dimethyl-
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9CI
7-HYDROXY-5-METHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE
5-methoxy-2,2-dimethylpyrano(3,2-g)chromen-8-one
5-Methoxy-8,8-dimethyl-2H,8H-pyrano(3,2-g)chromen-2-one
5-Methoxy-8,8-dimethyl-2H,8H-benzo(1,2-b:5,4-b')dipyran-2-one,9ci
DTXCID00155382
7-Hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-acrylic Acid delta-Lactone
CHEBI:69929
MLS000876794
CHEMBL501358
MEGxp0_001370
SCHEMBL5793283
ACon1_000545
HMS2269F07
HY-N1065
NSC35542
BDBM50428432
AKOS032962595
FS-8762
NCGC00168976-01
DA-59179
NCI60_003203
SMR000440571
XX163678
CS-0016348
5-methoxy-2,2-dimethyl-pyrano[3,2-g]chromen-8-one
BRD-K28556256-001-01-3
Q27138273
2H,2-b:5,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-
2-Propenoic acid,2-dimethyl-2H-1-benzopyran-6-yl)-, .delta.-lactone
NCGC00168976-02!5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
- Tsassi V, Hussain H, et al. (2010). Antimicrobial Coumarins from the Stem Bark of Afraegle paniculata. Natural Product Communications, 2010, 5(4), 559-561. [View] [PubMed]
- Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem:
66548
Cas:
84-99-1
Gnps:
CCMSLIB00000848039
Zinc:
ZINC000001668225
Chebi:
69929
Nmrshiftdb2:
60024116
Metabolights:
MTBLC69929
Chembl:
CHEMBL501358
Comptox:
DTXSID70232891
Bindingdb:
50428432
CPRiL:
108555
SMILES: c1cc(=O)oc(c12)cc3c(c2)C=CCO3
Level: 0
Mol. Weight: 258.27 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.63
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.17
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.12
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.07
- Plasma Protein Binding
- 37.44
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.93
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.56
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.65
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.67
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- 3.78
- Rat (Acute)
- 3.23
- Rat (Chronic Oral)
- 1.7
- Fathead Minnow
- 4.52
- 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
- 379.29
- Hydration Free Energy
- -8.44
- Log(D) at pH=7.4
- 2.89
- Log(P)
- 3.05
- Log S
- -4.11
- Log(Vapor Pressure)
- -5.59
- Melting Point
- 154.24
- pKa Acid
- 7.58
- pKa Basic
- 5.11
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.6323 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.5594 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.5077 |