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4-[(6-O-(5-O-(ferulic acid)-beta-apiofuranosyl)-beta-glucopyranoside)oxy]-5- methylcoumarin
- Family: Plantae - Ebenaceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Coumarin Glycoside Derivative
| Canonical Smiles | COc1cc(/C=C/C(=O)OCC2(O)CO[C@@H]([C@H]2O)OC[C@@H]2OC(Oc3cc(=O)oc4c3c(C)ccc4)[C@H]([C@@H]([C@H]2O)O)O)ccc1O |
|---|---|
| InChI | InChI=1S/C31H34O15/c1-15-4-3-5-18-24(15)20(11-23(34)44-18)45-29-27(37)26(36)25(35)21(46-29)12-41-30-28(38)31(39,14-43-30)13-42-22(33)9-7-16-6-8-17(32)19(10-16)40-2/h3-11,21,25-30,32,35-39H,12-14H2,1-2H3/b9-7+/t21-,25-,26+,27-,28+,29?,30-,31?/m0/s1 |
| InChIKey | XEBLEYTUAQNJBA-KMZNLYPMSA-N |
| Formula | C31H34O15 |
| HBA | 15 |
| HBD | 6 |
| MW | 646.6 |
| Rotatable Bonds | 10 |
| TPSA | 224.04 |
| LogP | -0.28 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 46 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.42 |
| Exact Mass | 646.19 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Diospyros bipindensis | Ebenaceae | Plantae | 413723 |
Showing of synonyms
4-[(6-O-(5-O-(ferulic acid)-beta-apiofuranosyl)-beta-glucopyranoside)oxy]-5- methylcoumarin
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OCC2CC(OC2)OCC3CCCC(O3)Oc4cc(=O)oc(c45)cccc5
Level: 3
Mol. Weight: 646.6 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CC(OC2)OCC3CCCCO3
Level: 2
Mol. Weight: 646.6 g/mol
SMILES: O1CCCC1OCC2CCCC(O2)Oc3cc(=O)oc(c34)cccc4
Level: 2
Mol. Weight: 646.6 g/mol
SMILES: c1cccc(c12)oc(=O)cc2OC3CCCCO3
Level: 1
Mol. Weight: 646.6 g/mol
SMILES: C1OCCC1COC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 646.6 g/mol
SMILES: O1CCCCC1COC2CCCO2
Level: 1
Mol. Weight: 646.6 g/mol
SMILES: c1cccc(c12)oc(=O)cc2
Level: 0
Mol. Weight: 646.6 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 646.6 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 646.6 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 646.6 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.48
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.880
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 40.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.040
- Plasma Protein Binding
- 74.47
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-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
- 6.850
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.980
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.830
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.900
- Micronucleos
- Toxic
- 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
- -74260.500
- Rat (Acute)
- 2.280
- Rat (Chronic Oral)
- 4.060
- Fathead Minnow
- 109.790
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 1926.250
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 1.190
- Log(P)
- 0.67
- Log S
- -4.18
- Log(Vapor Pressure)
- -127.29
- Melting Point
- 208.45
- pKa Acid
- 4.84
- pKa Basic
- 2.88
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9524 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9468 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9291 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.9192 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.9175 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9139 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9029 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8962 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8901 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8817 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8812 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8691 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8663 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8529 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8528 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8417 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8356 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8298 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8277 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8256 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8253 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8197 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8103 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8098 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8031 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8030 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7944 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 3 | 0.7812 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7807 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7745 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7729 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7673 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7667 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7662 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7651 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7636 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7604 |
| Eukaryotic translation initiation factor 4E-1 | P29557 | IF4E1_WHEAT | Triticum aestivum | 4 | 0.7600 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7600 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7594 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7589 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.7568 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7542 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7532 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7501 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7477 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7470 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7465 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7458 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7440 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7429 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7428 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7427 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7399 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7399 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7398 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7392 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7376 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7358 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7347 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7345 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7325 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7314 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7309 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7308 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7303 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7294 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7289 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7284 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7279 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7276 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 4 | 0.7271 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7265 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7254 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7246 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7241 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 2 | 0.7239 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7230 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7227 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7222 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7220 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7195 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7188 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7188 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7164 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7163 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7160 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7147 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7143 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7139 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7134 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7095 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.7089 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7085 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7084 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7081 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7074 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7073 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7073 |
| DNA (cytosine-5)-methyltransferase 3A | O88508 | DNM3A_MOUSE | Mus musculus | 3 | 0.7051 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7049 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7047 |
| Virulence sensor histidine kinase PhoQ | P0DM80 | PHOQ_SALTY | Salmonella typhimurium | 3 | 0.7044 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7043 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 3 | 0.7034 |
| Cell division control protein 42 homolog | P60953 | CDC42_HUMAN | Homo sapiens | 2 | 0.7022 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7014 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7013 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7012 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7012 |
| Transitional endoplasmic reticulum ATPase | P55072 | TERA_HUMAN | Homo sapiens | 3 | 0.7007 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7004 |