Select a section from the left sidebar
Quercetin 3-O-(6''-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC(COC2OC(C)C(C(C2O)O)O)C(C(C1O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3 |
| InChIKey | IKGXIBQEEMLURG-UHFFFAOYSA-N |
| Formula | C27H30O16 |
| HBA | 16 |
| HBD | 10 |
| MW | 610.52 |
| Rotatable Bonds | 6 |
| TPSA | 269.43 |
| LogP | -1.69 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 610.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Allium myrianthum | Amaryllidaceae | Plantae | 4678 |
| 2 | Withania somnifera | Solanaceae | Plantae | 126910 |
| 3 | Calendula officinalis | Asteraceae | Plantae | 41496 |
| 4 | Tephrosia vogelii | Leguminosae/Fabaceae | Plantae | 1157238 |
| 5 | Oncoba spinosa | Salicaceae | Plantae | 179733 |
Showing of synonyms
Quercetin 3-O-(6''-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
Vitamin P
Osyritin
Quercetin-3-o-rutinose
DL-Rutin
Rutosid
949926-49-2
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
10163-13-0
Venoruton
Ilixathin
1558680-22-0
Myrticalorin
Myticolorin
Rutinoside, .beta.-
Rutin, cadmium deriv.
3-Rhamnoglycosylquercetin
Quercetin 3-rhamnoglycoside
Quercetol 3-rhamnoglucodide
SCHEMBL23244
Quercetin-3.beta.-rutinoside
CHEMBL32579
SCHEMBL3764184
SCHEMBL21424757
CHEBI:91643
DTXSID70859300
BDBM237184
HMS3393B06
HMS3651K20
CCA52535
Quercetin 3-O-.beta.-D-rutinoside
NSC827563
STK682155
STL455123
AKOS001581212
AKOS021617510
NSC-408168
NSC-827563
SMP2_000101
NCGC00017207-02
NCGC00142380-01
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{3,4,5-trihydroxy-6-[(3,4,5-trihydroxy -6-methyl(2H-3,4,5,6-tetrahydropyran-2-yloxy))methyl](2H-3,4,5,6-tetrahydropyr an-2-yloxy)}chromen-4-one
Q1
3,4',5,7-Pentahydroxyflavone-3-rutinoside
Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy
BRD-A34907681-001-01-7
Q27163468
B0005-190152
Flavone,3',4',5,7-pentahydroxy-, 3-(O-rhamnosylglucoside)
Quercetin, 3-(6-O-.alpha.-L-rhamnopyranosyl-.beta.-D-glucopyranoside)
Rutinoside,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
Quercetin, 3-(6-0-(6-deoxy-.alpha.-L-mannopyranosyl-.beta.-D-glucopyranoside)
WLN: T66 BO EVJ CR CQ DQ & GQ IQ DO-BT6OTJ CQ DQ EQ F1O-BT6OTJ CQ DQ EQ F1
2-(3,4-dihydroxyphenyl)-4,5-dihydroxy-7-oxo-7H-chromen-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyltetrahydro-2H-2-pyranyloxymethyl)tetrahydro-2H-2-pyranyloxy)-4H-4-chromenone
2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-3-[(3,4,5-TRIHYDROXY-6-{[(3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL)OXY]METHYL}OXAN-2-YL)OXY]-4H-CHROMEN-4-ONE
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyl-2-oxanyl)oxymethyl]-2-oxanyl]oxy]-1-benzopyran-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside #
- Ukiya M, Akihisa T, et al. (2006). Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of Marigold (Calendula officinalis) flowers. Journal of Natural Products,2006,69,1692-1696. [View] [PubMed]
- Djouossi MG, Tamokou JD, et al. (2015). Antimicrobial and antioxidant flavonoids from the leaves of Oncoba spinosa Forssk. (Salicaceae).. BMC complementary and alternative medicine,2015, 15, 134. [View] [PubMed]
- Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
- El Shabrawy MOA, Hosni HA, et al. (2014). Flavonoids from Allium myrianthum Boiss.. Biochemical Systematics and Ecology,2014,56,125-128. [View]
- Kandil F, El Sayed N, et al. (1994). Flavonol Glycosides And Phenolics From Withania Somnifera. Phytochemistry, 1994, 37(4), 1215-1216. [View]
Pubchem:
5293655
Cas:
949926-49-2
Chebi:
91643
Nmrshiftdb2:
60023979
Chembl:
CHEMBL32579
Bindingdb:
237184
CPRiL:
15057
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 610.52 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 610.52 g/mol
Antimicrobial
Antioxidant
Absorption
- Caco-2 (logPapp)
- -6.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.53
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 8.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.74
- Plasma Protein Binding
- -4.46
- 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
- 13.23
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.58
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.97
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.85
- 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
- -13202.95
- Rat (Acute)
- 2.19
- Rat (Chronic Oral)
- 4.52
- Fathead Minnow
- 29.75
- 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
- 510.04
- Hydration Free Energy
- -3.1
- Log(D) at pH=7.4
- -1.22
- Log(P)
- -0.21
- Log S
- -4.36
- Log(Vapor Pressure)
- -14.2
- Melting Point
- 210.23
- pKa Acid
- 3.49
- pKa Basic
- 8.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9759 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9759 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8987 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8987 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8907 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8907 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8863 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8863 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8807 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8807 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8747 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8747 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8700 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8700 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8656 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8656 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8572 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8572 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8508 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8508 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8417 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8417 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8309 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8309 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8163 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8163 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8089 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8089 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8060 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8060 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8036 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8036 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8010 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8010 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7990 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7990 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7978 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7978 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7976 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7976 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7906 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7906 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7876 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7876 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7830 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7830 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7718 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7718 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7689 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7689 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7375 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7375 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7371 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7371 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 3 | 0.7349 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 3 | 0.7349 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7287 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7287 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7284 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7284 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7276 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7276 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7201 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7201 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7200 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7200 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7165 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7165 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7163 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7163 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7143 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7143 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7077 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7077 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7075 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7075 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7019 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7019 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7009 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7009 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7001 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7001 |