3-O-beta-arabinopyranosyl-(+)-taxifolin - Compound Card

3-O-beta-arabinopyranosyl-(+)-taxifolin

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3-O-beta-arabinopyranosyl-(+)-taxifolin

Structure
Zoomed Structure
  • Family: Plantae - Rosaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)O[C@@H]([C@H](C2=O)OC1OC[C@H]([C@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C20H20O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17-26,28H,6H2/t12-,15-,17+,18-,19+,20?/m1/s1
InChIKey UKSPRKDZNYSFRL-HBQSKOGZSA-N
Formula C20H20O11
HBA 11
HBD 7
MW 436.37
Rotatable Bonds 3
TPSA 186.37
LogP -0.35
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 436.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Crataegus sinaica Rosaceae Plantae 298646

Showing of synonyms

  • Shahat AA, Ismail SI, et al. (1998). Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine,1998,5(2),133-136. [View] [PubMed]
Pubchem: 162887299

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)OC4CCCCO4

Level: 2

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1cccc(c12)OCC(C2=O)OC3CCCCO3

Level: 1

Mol. Weight: 436.37 g/mol

Structure

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

Level: 1

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 436.37 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
69.63
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
16.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.71
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.33
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
-42.41
Rat (Acute)
2.31
Rat (Chronic Oral)
3.87
Fathead Minnow
3.9
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
596.4
Hydration Free Energy
-7.41
Log(D) at pH=7.4
0.32
Log(P)
0.17
Log S
-3.55
Log(Vapor Pressure)
-11.9
Melting Point
202.76
pKa Acid
5.11
pKa Basic
6.89
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 3 0.9175
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9175
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8777
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8777
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8668
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8668
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8560
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8560
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8534
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8534
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8509
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8509
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8414
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8414
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8303
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8303
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8300
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8300
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8267
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8267
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8259
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8259
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8210
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8210
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8084
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8084
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7999
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7999
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7988
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7988
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7976
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7976
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7947
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7947
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7926
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7926
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7925
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7925
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7843
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7843
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7804
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7804
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7732
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7732
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7732
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7732
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7680
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7680
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7606
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7606
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7599
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7599
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7588
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7588
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7583
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7583
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7575
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7575
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7561
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7561
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7505
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7505
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7451
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7451
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7435
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7435
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7409
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7409
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7395
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7395
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7383
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7383
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7377
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7377
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7342
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7342
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7281
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7281
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7277
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7277
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7269
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7269
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7257
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7257
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7255
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7255
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7250
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7250
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7244
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7244
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7232
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7232
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7191
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7191
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7141
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7141
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7084
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7084
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7082
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7082
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7081
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7081
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7064
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7064
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7028
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7028
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7021
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7021
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7009
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7009

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