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7,8,9-trimethoxycoumarin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | COc1c(OC)c(OC)cc2c1oc(=O)cc2 |
|---|---|
| InChI | InChI=1S/C12H12O5/c1-14-8-6-7-4-5-9(13)17-10(7)12(16-3)11(8)15-2/h4-6H,1-3H3 |
| InChIKey | RAYQKHLZHPFYEJ-UHFFFAOYSA-N |
| Formula | C12H12O5 |
| HBA | 5 |
| HBD | 0 |
| MW | 236.22 |
| Rotatable Bonds | 3 |
| TPSA | 57.9 |
| LogP | 1.82 |
| Number Rings | 2 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 236.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Zanthoxylum tessmannii | Rutaceae | Plantae | 1291627 |
Showing of synonyms
7,8,9-trimethoxycoumarin
6,7,8-Trimethoxycoumarin
6,7,8-Trimethoxy-2H-chromen-2-one
112-421-8
Dimethylfraxetin
6035-49-0
6,7,8-trimethoxychromen-2-one
Fraxidin Methyl Ether
6,7,8,-trimethoxycoumarin
CHEMBL253551
Fraxetin dimethyl ether
Di-O-methylfraxetin
2H-1-Benzopyran-2-one, 6,7,8-trimethoxy-
KBio1_001126
O,o-Dimethylfraxetin
MFCD00145039
Spectrum_000635
SpecPlus_000086
2H-Benzopyran-2-one, 6,7,8-trimethoxy-
Spectrum2_000357
Spectrum3_000111
Spectrum4_001392
Spectrum5_000124
BSPBio_001722
KBioGR_001744
KBioSS_001115
SPECTRUM100572
DivK1c_006182
SPBio_000453
SCHEMBL2464275
CHEBI:93172
KBio2_001115
KBio2_003683
KBio2_006251
KBio3_000862
DTXSID00209112
RAYQKHLZHPFYEJ-UHFFFAOYSA-N
HMS3749G11
HY-N0085
BDBM50428439
CCG-38632
AKOS016009536
6,7,8-trimethoxy-1-benzopyran-2-one
CS-7783
FT65839
SDCCGMLS-0066335.P001
NCGC00095436-01
NCGC00095436-02
NCGC00179059-01
AC-34018
MS-23367
DB-333286
SR-05000002478
SR-05000002478-1
BRD-K66944906-001-01-8
Q27164894
InChI=1/C12H12O5/c1-14-8-6-7-4-5-9(13)17-10(7)12(16-3)11(8)15-2/h4-6H,1-3H
Pubchem:
3083928
Cas:
6035-49-0
Gnps:
CCMSLIB00006456618
Zinc:
ZINC000002516970
Chebi:
93172
Nmrshiftdb2:
75778
Chembl:
CHEMBL253551
Comptox:
DTXSID00209112
Bindingdb:
50428439
No compound-protein relationship available.
SMILES: c1cccc(c12)oc(=O)cc2
Level: 0
Mol. Weight: 236.22 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -4.41
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.940
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.010
- Plasma Protein Binding
- 48.32
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-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
- 4.480
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.700
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.500
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.180
- 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
- 3.410
- Rat (Acute)
- 2.370
- Rat (Chronic Oral)
- 1.700
- Fathead Minnow
- 4.410
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 351.690
- Hydration Free Energy
- -8.960
- Log(D) at pH=7.4
- 1.250
- Log(P)
- 1.56
- Log S
- -1.99
- Log(Vapor Pressure)
- -4.64
- Melting Point
- 123.99
- pKa Acid
- 6.65
- pKa Basic
- 0.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9738 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9385 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9321 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9321 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9296 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.9225 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9191 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9098 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8930 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8613 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8516 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8475 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8222 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8089 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8051 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.8008 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8000 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7948 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7902 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7878 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7778 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7737 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7649 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7576 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7527 |
| O-GlcNAcase NagJ | Q0TR53 | OGA_CLOP1 | Clostridium perfringens | 3 | 0.7490 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7488 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7478 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7402 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7397 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7384 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7382 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7337 |
| Nucleoside permease | Q9KPL5 | Q9KPL5_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7324 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7315 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7305 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7291 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7264 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7242 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7228 |
| Cyclic nucleotide-binding domain-containing protein | E0RR11 | E0RR11_SPITD | Spirochaeta thermophila | 2 | 0.7180 |
| D-mycarose 3-C-methyltransferase | Q194Q4 | Q194Q4_STRAA | Streptomyces argillaceus | 4 | 0.7177 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7177 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7171 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7146 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7094 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7082 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7072 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7068 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7064 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7048 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 2 | 0.7047 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7038 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7037 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7008 |