Quercetin 3-O-[beta-D-glucopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→6)-(4 trans-p-coumaroyl)]-beta-D-galactopyranoside
- Family: Plantae - Gentianaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: P-Coumaroyl Flavonol Glycoside
| Canonical Smiles | OCC1O[C@@H](OC2C(O)OC(C(C2O)O)OC2C(C)OC(C(C2O)O)OCC2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)O)O)[C@H]([C@H]([C@H]2OC(=O)/C=C/c2ccc(cc2)O)O)O)[C@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C47H54O28/c1-15-38(72-47-37(64)33(60)42(43(65)75-47)74-45-34(61)30(57)28(55)24(13-48)69-45)31(58)35(62)44(67-15)66-14-25-40(71-26(54)9-4-16-2-6-18(49)7-3-16)32(59)36(63)46(70-25)73-41-29(56)27-22(53)11-19(50)12-23(27)68-39(41)17-5-8-20(51)21(52)10-17/h2-12,15,24-25,28,30-38,40,42-53,55,57-65H,13-14H2,1H3/b9-4+/t15?,24?,25?,28-,30+,31?,32-,33?,34+,35?,36+,37?,38?,40+,42?,43?,44?,45+,46+,47?/m1/s1 |
| InChIKey | DCORWUJVWKUYCL-RCUSCMPMSA-N |
| Formula | C47H54O28 |
| HBA | 28 |
| HBD | 16 |
| MW | 1066.92 |
| Rotatable Bonds | 14 |
| TPSA | 454.03 |
| LogP | -4.11 |
| Number Rings | 8 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 75 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.49 |
| Exact Mass | 1066.28 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurium spicatum | Gentianaceae | Plantae | 172074 |
Showing of synonyms
- Allam A, Nafady A, et al. (2016). Two new P-coumaroyl flavonoid glycosides having cytokine increasing activity from Centaurium spicatum L. Phytochemistry Letters, 2016, 17, 144-151. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCC(OC(=O)C=Cc5ccccc5)C4COC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8
Level: 6
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCC(OC(=O)C=Cc5ccccc5)C4COC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCCC4COC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OC5)CCC5OC6CCCCO6
Level: 4
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6
Level: 4
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCCC3COC(OC4)CCC4OC(OC5)CCC5OC6CCCCO6
Level: 4
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC(OC4)CCC4OC5CCCCO5
Level: 4
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6
Level: 4
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)coc(c45)cccc5
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC4CCCCO4
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1COC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4
Level: 3
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC3CCCCO3
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1COC(OC2)CCC2OC3CCCCO3
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3
Level: 2
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 1066.92 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 1066.92 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 1066.92 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 1066.92 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 1066.92 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 1066.92 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 1066.92 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.47
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 314523.54
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 41105511.32
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- -0.65
- 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
- 6.4
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -956010.53
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.06
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.05
- 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
- -74604510636.34
- Rat (Acute)
- 2.52
- Rat (Chronic Oral)
- 160.29
- Fathead Minnow
- 94172245.01
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 8390928909.14
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -4659.21
- Log(P)
- -0.69
- Log S
- -5.65
- Log(Vapor Pressure)
- -276308952.33
- Melting Point
- 228.8
- pKa Acid
- -2013276.62
- pKa Basic
- -16187.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9770 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8920 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8751 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8718 |
| Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.8438 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8376 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8352 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8290 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8081 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7962 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7918 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7896 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7857 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7833 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7787 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7762 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7718 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7667 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7656 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7637 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7527 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7469 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7463 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7445 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7410 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7401 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7375 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7352 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7333 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7264 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7218 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7141 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7067 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7053 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7038 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.7028 |