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4-hydroxy-5-methylcoumarin-4-O-beta-D-glucopyranoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Coumarin Glycoside
| Canonical Smiles | O=c1cc(OC[C@H]2O[C@@H](O)[C@@H]([C@H]([C@@H]2O)O)O)c2c(o1)cccc2C |
|---|---|
| InChI | InChI=1S/C16H18O8/c1-7-3-2-4-8-12(7)9(5-11(17)23-8)22-6-10-13(18)14(19)15(20)16(21)24-10/h2-5,10,13-16,18-21H,6H2,1H3/t10-,13-,14+,15-,16-/m1/s1 |
| InChIKey | VCBBBBBZESNDRG-LMXXTMHSSA-N |
| Formula | C16H18O8 |
| HBA | 8 |
| HBD | 4 |
| MW | 338.31 |
| Rotatable Bonds | 3 |
| TPSA | 129.59 |
| LogP | -0.72 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 338.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ethulia conyzoides | Asteraceae | Plantae | 434659 |
| 2 | Ethulia conyzoides | Asteraceae | Plantae | 434659 |
Showing of synonyms
4-hydroxy-5-methylcoumarin-4-O-beta-D-glucopyranoside
- Mahmoud ZF, Sarg TM, et al. (1980). A 5-methylcoumarin glucoside from Ethulia conyzoides. Phytochemistry,1980,19,2029-2030. [View]
- Mahmoud AA, Ahmed AA, et al. (1998). Further monoterpene 5-methylcooumarins and an acetophenone derivative from Ethulia conyzoides. Phytochemistry,1998,48(3),543-546. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1COc2cc(=O)oc(c23)cccc3
Level: 1
Mol. Weight: 338.31 g/mol
SMILES: c1cccc(c12)oc(=O)cc2
Level: 0
Mol. Weight: 338.31 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 338.31 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.31
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.75
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.61
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.0
- Plasma Protein Binding
- 75.03
- 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
- Non-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
- 5.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.72
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.17
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.1
- 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
- -1.45
- Rat (Acute)
- 2.45
- Rat (Chronic Oral)
- 3.3
- Fathead Minnow
- 3.99
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 468.57
- Hydration Free Energy
- -15.67
- Log(D) at pH=7.4
- 0.24
- Log(P)
- -0.85
- Log S
- -2.11
- Log(Vapor Pressure)
- -12.17
- Melting Point
- 176.51
- pKa Acid
- 5.56
- pKa Basic
- 5.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.9843 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.9843 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8480 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8480 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8339 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8339 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8287 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8287 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7983 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7983 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7974 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7974 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7951 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7951 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7936 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7936 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7926 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7926 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7872 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7872 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7825 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7825 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7815 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7815 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7798 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7798 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7768 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7768 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7746 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7746 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7639 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7639 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7537 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7537 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7530 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7530 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7409 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7409 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7398 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7398 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7383 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7383 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7374 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7374 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7345 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7345 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7344 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7344 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7336 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7336 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7335 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7335 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7306 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7306 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7290 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7290 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7264 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7264 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7242 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7242 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7232 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7232 |
| Casein kinase I isoform gamma-2 | P78368 | KC1G2_HUMAN | Homo sapiens | 3 | 0.7223 |
| Casein kinase I isoform gamma-2 | P78368 | KC1G2_HUMAN | Homo sapiens | 3 | 0.7223 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7200 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7200 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7171 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7171 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7168 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7168 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7168 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7168 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.7165 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.7165 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7162 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7162 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7127 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7127 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7126 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7126 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7066 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7066 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7059 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7059 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7057 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7057 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.7050 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.7050 |
| DNA topoisomerase 1 | P06612 | TOP1_ECOLI | Escherichia coli | 3 | 0.7045 |
| DNA topoisomerase 1 | P06612 | TOP1_ECOLI | Escherichia coli | 3 | 0.7045 |