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Myricetin-3-glucoside

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

Canonical Smiles	OC[C@H]1OC(Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2cc(O)c(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H20O13/c22-5-12-15(28)17(30)18(31)21(33-12)34-20-16(29)13-8(24)3-7(23)4-11(13)32-19(20)6-1-9(25)14(27)10(26)2-6/h1-4,12,15,17-18,21-28,30-31H,5H2/t12-,15-,17+,18-,21?/m1/s1
InChIKey	FOHXFLPXBUAOJM-OWORMUAASA-N
Formula	C₂₁H₂₀O₁₃
HBA	13
HBD	9
MW	480.38
Rotatable Bonds	4
TPSA	230.74
LogP	-0.83
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	480.09
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pistacia lentiscus	Anacardiaceae	Plantae	371726
2	Pistacia khinjuk	Anacardiaceae	Plantae	434236
3	Argania spinosa	Sapotaceae	Plantae	2945705

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]
Kawashty SA, Mosharrafa SAM, et al. (2000). The flavonoids of four Pistacia species in Egypt. Biochemical Systematics and Ecology,2000,28(9),915-917. [View] [PubMed]

Pubchem: 22841567

Nmrshiftdb2: 60030889

Chembl: CHEMBL2282026

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 480.38 g/mol

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

Level: 1

Mol. Weight: 480.38 g/mol

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

Level: 1

Mol. Weight: 480.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 480.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 480.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 480.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.22
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.2
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.71
Plasma Protein Binding: 68.9
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: 13.48
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.95
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.04
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: -157.94
Rat (Acute): 2.41
Rat (Chronic Oral): 3.99
Fathead Minnow: 3.54
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: 688.5
Hydration Free Energy: -4.21
Log(D) at pH=7.4: -0.81
Log(P): 0.11
Log S: -4.14
Log(Vapor Pressure): -12.32
Melting Point: 209.73
pKa Acid: 5.37
pKa Basic: 9.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8965
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8965
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8825
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8825
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8643
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8643
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8609
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8609
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8540
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8540
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8434
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8434
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8421
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8421
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8400
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8400
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8399
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8399
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8340
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8340
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8218
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8218
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8194
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8194
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8163
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8163
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8158
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8158
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8125
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8125
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.8090
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.8090
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7786
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7786
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7769
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7769
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7721
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7721
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7718
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7718
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7690
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7690
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7689
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7689
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7662
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7662
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7631
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7631
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7563
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7563
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7541
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7541
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7436
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7436
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7426
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7426
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7395
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7395
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7319
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7319
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7164
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7164
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7129
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7129
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7129
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7129
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7102
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7102
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7087
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7087
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7056
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7056
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7028
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7028

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