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Taxifolin 4′-O-beta-D-glucopyranoside

Family: Cistaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol Glycoside

Canonical Smiles	OC[C@@H]1OC(Oc2ccc(cc2O)C2CC(=O)c3c(O2)cc(cc3O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C21H22O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-13-2-1-8(3-10(13)24)14-6-12(26)17-11(25)4-9(23)5-15(17)30-14/h1-5,14,16,18-25,27-29H,6-7H2/t14?,16-,18-,19+,20-,21?/m0/s1
InChIKey	ZKMIRYADZQAFFT-LVGRFBRNSA-N
Formula	C₂₁H₂₂O₁₁
HBA	11
HBD	7
MW	450.4
Rotatable Bonds	4
TPSA	186.37
LogP	-0.31
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	450.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Halimium halimifolium	Cistaceae	Plantae	632747

Showing of synonyms

Kerbab K, Sansone F, et al. (2019). Halimium halimifolium: From the Chemical and Functional Characterization to a Nutraceutical Ingredient Design. Planta medica, 2019, 85(11-12), 1024-1033. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2=O)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 324.38 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 224.26 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 178.23 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 148.16 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.89
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 66.69
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: 14.68
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.41
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.69
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.83
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: -70.69
Rat (Acute): 2.26
Rat (Chronic Oral): 4.13
Fathead Minnow: 4.19
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: 580.01
Hydration Free Energy: -4.59
Log(D) at pH=7.4: 0.28
Log(P): 0.12
Log S: -4.06
Log(Vapor Pressure): -12.69
Melting Point: 216.44
pKa Acid: 5.08
pKa Basic: 6.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9220
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.9193
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.9091
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8954
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8951
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8760
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8758
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8731
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8728
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8699
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8686
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8672
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8665
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8551
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8526
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8521
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.8470
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8412
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8378
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8351
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.8298
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8243
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8182
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8151
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8112
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8063
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8050
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8007
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7983
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7982
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7961
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7929
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7921
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7919
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7883
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7856
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7825
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7812
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7782
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7770
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7768
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7757
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7749
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7716
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7704
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7681
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7677
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7675
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7671
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7668
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7615
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7614
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7600
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7565
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7555
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7551
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7522
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7505
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7492
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7474
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7456
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7451
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7446
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7444
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7439
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7439
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7413
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7391
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7370
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7367
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7361
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7347
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7346
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7342
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7342
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7340
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7297
Beta-glucosidase	Q8T0W7	Q8T0W7_9NEOP	Neotermes koshunensis	4	0.7266
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7213
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7210
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7204
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7202
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7198
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7192
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7190
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7182
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7169
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7164
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7163
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7160
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7159
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7146
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7141
RNA-directed RNA polymerase	P11124	RDRP_BPPH6	Pseudomonas phage phi6	4	0.7117
Rac-like GTP-binding protein ARAC7	O82480	RAC7_ARATH	Arabidopsis thaliana	3	0.7113
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7112
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7089
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7086
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	4	0.7083
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7065
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7063
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7058
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7033
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7018
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7010
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7004

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