Taxifolin 3-O-alpha-rhamnopyranoside - Compound Card

Taxifolin 3-O-alpha-rhamnopyranoside

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Taxifolin 3-O-alpha-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Ericaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)O[C@@H]([C@H](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/C21H22O11/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/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1
InChIKey ZROGCCBNZBKLEL-MPRHSVQHSA-N
Formula C21H22O11
HBA 11
HBD 7
MW 450.4
Rotatable Bonds 3
TPSA 186.37
LogP 0.04
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 Neurada procumbens Neuradaceae Plantae 32215
2 Neurada procumbens Neuradaceae Plantae 32215
3 Parinari hypochrysea Chrysobalanaceae Plantae 82156
4 Erica mannii Ericaceae Plantae 2984617

Showing of synonyms

  • Adjapmoh M, Toze F, et al. (2016). A new ceramide and biflavonoid from the leaves of Parinari hypochrysea (Chrysobalanaceae).. Natural Product Communications, 2016, 11(5), 615-620. [View] [PubMed]
  • Bitchagno GT, Tankeo SB, et al. (2016). Ericoside, a new antibacterial biflavonoid from Erica mannii (Ericaceae).. Fitoterapia,2016, 109, 206-211. [View] [PubMed]
  • Marzouk MM, Hussein SR, et al. (2014). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Biochemical Systematics and Ecology,2014,57,67-68. [View]
  • Marzouk M, Hussein SR, et al. (2013). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Planta Medica,2013,79-PI46. [View]
CPRiL: 59511
Structure

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

Level: 2

Mol. Weight: 450.4 g/mol

Structure

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

Level: 1

Mol. Weight: 450.4 g/mol

Structure

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

Level: 1

Mol. Weight: 450.4 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 450.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 450.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.4 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-6.88
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
Substrate
Skin Permeability
-0.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
77.15
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
15.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Safe
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
-61.47
Rat (Acute)
2.25
Rat (Chronic Oral)
4.06
Fathead Minnow
3.81
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
589.05
Hydration Free Energy
-5.8
Log(D) at pH=7.4
0.42
Log(P)
0.7
Log S
-4.65
Log(Vapor Pressure)
-11.35
Melting Point
194.48
pKa Acid
5.23
pKa Basic
6.52
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 0.9215
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9215
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8885
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8885
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8884
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8884
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8569
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8569
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8502
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8502
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8483
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8483
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8309
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8309
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8211
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8211
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8146
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8146
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8074
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8057
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8055
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8013
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8013
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7950
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7950
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7935
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7935
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7913
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7913
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7873
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7873
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7855
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7855
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7836
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7836
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7825
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7825
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7746
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7746
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7671
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7671
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7666
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7666
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7656
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7656
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7638
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7638
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7633
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7633
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7633
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7633
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7625
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7625
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7611
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7611
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7543
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7543
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7520
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7503
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7503
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7461
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7461
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7444
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7444
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7417
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7417
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7401
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7401
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7397
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7397
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7360
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7360
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7347
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7347
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7322
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7322
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7317
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7317
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7291
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7213
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7213
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7196
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7196
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7183
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7183
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7180
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7180
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7141
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7141
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7108
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7108
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7051
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7051
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7026
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7026

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