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Quercetin 3-O-alpha-L-rhamnopyronside

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m1/s1
InChIKey	OXGUCUVFOIWWQJ-JHPRLSDPSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	7
MW	448.38
Rotatable Bonds	3
TPSA	190.28
LogP	0.49
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eugenia jambolana	Myrtaceae	Plantae	260142

Showing of synonyms

Mahmoud I.I, Marzouk M.S, et al. (2001). Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry, 2001, 58(8), 1239-44. [View] [PubMed]

Pubchem: 15939939

Zinc: ZINC000014952519

Nmrshiftdb2: 30095862

Chembl: CHEMBL2262641

Bindingdb: 50129557

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.71
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 85.09
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: 14.35
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.77
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.21
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.63
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: -62.25
Rat (Acute): 2.37
Rat (Chronic Oral): 3.96
Fathead Minnow: 3.71
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: 626.38
Hydration Free Energy: -6.04
Log(D) at pH=7.4: 0.6
Log(P): 1.08
Log S: -4.14
Log(Vapor Pressure): -11.41
Melting Point: 203.72
pKa Acid: 4.65
pKa Basic: 7.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9685
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9036
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9035
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8983
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8918
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8863
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8727
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8625
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8610
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8552
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8505
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8403
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8313
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8175
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8167
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8158
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8094
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8074
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8040
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7996
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7938
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7870
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7834
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7790
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7761
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7729
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7671
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7656
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7625
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7583
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7578
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7567
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7564
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7519
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7456
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7448
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7437
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7417
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7399
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7367
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7350
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7284
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7258
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7255
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7175
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	3	0.7161
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7161
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7155
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7147
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7070
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7064
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7016
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7002

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