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Quercetin-3-O–arabinose

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

Canonical Smiles	OCC1OC(C(C1O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2
InChIKey	BDCDNTVZSILEOY-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₁₁
HBA	11
HBD	7
MW	434.35
Rotatable Bonds	4
TPSA	190.28
LogP	0.1
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	434.08
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Argania spinosa	Sapotaceae	Plantae	2945705
2	Monanthotaxis discolor	Annonaceae	Plantae	2231809
3	Eucalyptus camaledulensis	Myrtaceae	Plantae	34316

Showing of synonyms

Mercolini L, Protti M, et al. (2016). Analytical profiling of bioactive phenolic compounds in argan (Argania spinosa) leaves by combined microextraction by packed sorbent (MEPS) and LC-DAD-MS/MS. Phytochemical analysis : PCA,2016, 27(1), 41-9. [View] [PubMed]
Sumary DP, Mgina CA, et al. (2020). Isolation and antimicrobial activities of a novel discolornolide and other compounds from Monanthotaxis discolor. Natural product research,2020, 34(22), 3163-3168. [View] [PubMed]
Singab A-N, Ayoub N, et al. (2011). Phenolic Constituents of Eucalyptus camaldulensis Dehnh, with Potential Antioxidant and Cytotoxic Activities. Records of Natural Products,2011,5(4),271-280. [View]

Pubchem: 12308704

Cas: 5041-68-9

Nmrshiftdb2: 60028472

No compound-protein relationship available.

SMILES: O1CCCC1Oc(c2=O)c(-c3ccccc3)oc(c24)cccc4

Level: 2

Mol. Weight: 434.35 g/mol

SMILES: O1CCCC1Oc(c2=O)coc(c23)cccc3

Level: 1

Mol. Weight: 434.35 g/mol

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

Level: 1

Mol. Weight: 434.35 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 434.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.35 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 434.35 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.36
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.68
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.88
Plasma Protein Binding: 48.95
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 13.49
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.31
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.91
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: -46.34
Rat (Acute): 2.47
Rat (Chronic Oral): 3.67
Fathead Minnow: 3.96
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: 600.26
Hydration Free Energy: -6.82
Log(D) at pH=7.4: 0.46
Log(P): 1.12
Log S: -4.13
Log(Vapor Pressure): -9.9
Melting Point: 216.26
pKa Acid: 6.08
pKa Basic: 7.0

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9743
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9041
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9024
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9019
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8910
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8789
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8747
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8747
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8741
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8712
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8691
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8638
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.8634
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8621
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8535
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8440
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8342
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8307
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8263
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8235
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8228
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8168
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8147
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8134
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8108
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8104
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8092
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8074
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8051
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8015
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8014
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7994
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7969
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7926
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7913
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7899
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7873
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7833
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7818
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7803
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7800
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7790
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7741
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7729
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7665
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7653
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7639
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7634
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7622
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7597
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7584
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7582
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7559
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7554
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7543
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7539
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7512
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7485
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7480
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7463
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7410
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7354
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7349
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7288
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7288
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7281
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7278
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	4	0.7260
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7256
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	4	0.7205
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7202
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7200
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7182
Serine/threonine-protein kinase RAD53	P22216	RAD53_YEAST	Saccharomyces cerevisiae	4	0.7177
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7113
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7108
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7107
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7094
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7091
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7080
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7075
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7038
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7037
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7035
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7030
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7018

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