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Isorhamnetin-3-O-beta-glucopyranoside
- Family: Plantae - Resedaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Cc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C23H24O11/c1-32-14-4-9(2-3-12(14)26)23-11(7-16-20(29)22(31)21(30)17(8-24)33-16)19(28)18-13(27)5-10(25)6-15(18)34-23/h2-6,16-17,20-22,24-27,29-31H,7-8H2,1H3/t16-,17+,20-,21+,22+/m0/s1 |
| InChIKey | PHNFQMVPALRYEB-LJQVGOIWSA-N |
| Formula | C23H24O11 |
| HBA | 11 |
| HBD | 7 |
| MW | 476.43 |
| Rotatable Bonds | 5 |
| TPSA | 190.28 |
| LogP | -0.03 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.35 |
| Exact Mass | 476.13 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Randonia africana | Resedaceae | Plantae | 415773 |
Showing of synonyms
Isorhamnetin-3-O-beta-glucopyranoside
- Berrehal D, Khalfallah A, et al. (2010). Flavonoid glycosides from Randonia africana Coss. (Resedaceae). Biochemical Systematics and Ecology,2010,38(5),1007-1009. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1Cc(c2=O)c(-c3ccccc3)oc(c24)cccc4
Level: 2
Mol. Weight: 476.43 g/mol
SMILES: O1CCCCC1Cc(c2=O)coc(c23)cccc3
Level: 1
Mol. Weight: 476.43 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 476.43 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 476.43 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 476.43 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 476.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.58
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.560
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.860
- Plasma Protein Binding
- 77.16
- 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
- 13.830
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.410
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.980
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.290
- 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
- -185.840
- Rat (Acute)
- 2.410
- Rat (Chronic Oral)
- 4.110
- Fathead Minnow
- 3.930
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 636.180
- Hydration Free Energy
- -3.830
- Log(D) at pH=7.4
- 0.340
- Log(P)
- 0.11
- Log S
- -4.68
- Log(Vapor Pressure)
- -11.79
- Melting Point
- 189.53
- pKa Acid
- 5.19
- pKa Basic
- 7.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9323 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9323 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9106 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9106 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9086 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9086 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8910 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8910 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8821 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8821 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8753 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8753 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8723 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8723 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8620 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8620 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8403 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8403 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8375 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8375 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8335 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8335 |
| Heat shock protein HSP 90-beta | P08238 | HS90B_HUMAN | Homo sapiens | 3 | 0.8333 |
| Heat shock protein HSP 90-beta | P08238 | HS90B_HUMAN | Homo sapiens | 3 | 0.8333 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8293 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8293 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8269 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8269 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8136 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8136 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8128 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8128 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8103 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8103 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.8022 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.8022 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7976 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7976 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7938 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7938 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7894 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7894 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.7863 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.7863 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7796 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7796 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7791 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7791 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7751 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7751 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7729 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7729 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7698 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7698 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7646 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7646 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7635 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7635 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7616 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7616 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7539 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7539 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7494 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7494 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.7473 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.7473 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7461 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7461 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 4 | 0.7453 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 4 | 0.7453 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7434 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7434 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7423 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7423 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7412 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7412 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7410 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7410 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7405 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7405 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7397 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7397 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7393 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7393 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7332 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7332 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7331 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7331 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7294 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7294 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7290 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7290 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7269 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7269 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7258 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7258 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7244 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7244 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7232 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7232 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7173 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7173 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7160 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7160 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7159 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7159 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7152 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7152 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7151 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7151 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7149 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7149 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 3 | 0.7144 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 3 | 0.7144 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.7139 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.7139 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7122 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7122 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7102 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7102 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7050 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7050 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7017 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7017 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7016 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7016 |