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Quercetin-3-O-alpha-L-rhamnopyranosyl-(l→6)-beta-D-glucopyranoside

Family: Plantae - Cucurbitaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OC[C@H]1OC(O[C@@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)O)O)[C@@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C26H28O17/c27-6-13-15(32)17(34)19(36)24(40-13)42-26-21(38)18(35)20(37)25(43-26)41-23-16(33)14-11(31)4-8(28)5-12(14)39-22(23)7-1-2-9(29)10(30)3-7/h1-5,13,15,17-21,24-32,34-38H,6H2/t13-,15-,17+,18+,19-,20-,21-,24?,25-,26-/m1/s1
InChIKey	XCTXPQAJEYGWPW-MQQQLUACSA-N
Formula	C₂₆H₂₈O₁₇
HBA	17
HBD	11
MW	612.49
Rotatable Bonds	6
TPSA	289.66
LogP	-2.76
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	612.13
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fraxinus oxycarba	Oleaceae	Plantae	38871
2	Cucumis melo	Cucurbitaceae	Plantae	3656

Showing of synonyms

Ibrahim S.R.M, Khedr A.I.M, et al. (2019). Cucumol B, a new triterpene benzoate from Cucumis melo seeds with cytotoxic effect toward ovarian and human breast adenocarcinoma. Journal of Asian natural products research, 2019, 21(11), 1112-1118. [View] [PubMed]
Hosny M (1998). Secoiridoid glucosides from Fraxinus oxycarba. Phytochemistry,1998,47(8),1569-1576. [View]

Pubchem: 162817140

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCC(O4)OC5CCCCO5

Level: 3

Mol. Weight: 612.49 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCC(O3)OC4CCCCO4

Level: 2

Mol. Weight: 612.49 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 612.49 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 612.49 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 612.49 g/mol

SMILES: O1CCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 612.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 612.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 612.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 612.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.43
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.7
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 10.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.66
Plasma Protein Binding: 59.0
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: 10.19
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.1
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.99
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.4
Micronucleos: Toxic
NR-AhR: Toxic
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: -13652.32
Rat (Acute): 2.22
Rat (Chronic Oral): 4.26
Fathead Minnow: 29.02
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 519.65
Hydration Free Energy: -2.94
Log(D) at pH=7.4: -1.52
Log(P): -0.67
Log S: -4.61
Log(Vapor Pressure): -14.53
Melting Point: 217.36
pKa Acid: 2.94
pKa Basic: 10.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9039
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9039
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8870
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8870
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8820
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8820
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8745
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8745
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8738
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8738
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8269
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8269
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8149
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8149
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8130
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8130
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8127
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8127
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8051
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8051
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8007
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8007
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7925
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7925
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7868
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7868
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7865
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7865
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7854
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7854
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7772
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7772
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7756
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7756
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7744
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7744
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7738
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7738
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7732
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7732
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7727
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7727
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7704
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7704
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7650
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7650
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7630
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7630
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7604
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7604
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7601
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7601
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7556
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7556
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7496
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7496
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7434
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7434
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7403
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7403
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7391
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7391
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7303
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7303
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7301
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7301
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7228
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7228
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7226
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7226
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7181
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7181
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7136
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7136
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7085
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7085
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7067
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7067
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7016
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7016

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