(+)-4'-methylgallocatechin 3'-O-beta-D-glucopyranoside - Compound Card

(+)-4'-methylgallocatechin 3'-O-beta-D-glucopyranoside

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(+)-4'-methylgallocatechin 3'-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc(cc(c2OC)O)[C@H]2Oc3cc(O)cc(c3C[C@@H]2O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H26O12/c1-31-21-12(26)2-8(20-13(27)6-10-11(25)4-9(24)5-14(10)32-20)3-15(21)33-22-19(30)18(29)17(28)16(7-23)34-22/h2-5,13,16-20,22-30H,6-7H2,1H3/t13-,16+,17+,18-,19+,20+,22+/m0/s1
InChIKey FHINLKPLNHTRNY-JLLDPRJFSA-N
Formula C22H26O12
HBA 12
HBD 8
MW 482.44
Rotatable Bonds 5
TPSA 198.76
LogP -0.97
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 482.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Maytenus senegalensis Celastraceae Plantae 256095

Showing of synonyms

  • Hussein G, Miyashiro H, et al. (1999). Inhibitory effects of Sudanese plant extracts on HIV-1 replication and HIV-1 protease. Phytotherapy Research,1999,13(1),31-36. [View] [PubMed]
Pubchem: 476782
Nmrshiftdb2: 70023442

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2)c3cc(ccc3)OC4CCCCO4

Level: 2

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 482.44 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 482.44 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 482.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
66.65
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
13.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.680
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.230
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
-179.490
Rat (Acute)
2.140
Rat (Chronic Oral)
4.020
Fathead Minnow
3.740
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
611.970
Hydration Free Energy
-3.690
Log(D) at pH=7.4
-0.180
Log(P)
-1.38
Log S
-4.14
Log(Vapor Pressure)
-12.33
Melting Point
188.52
pKa Acid
5.13
pKa Basic
6.25
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 0.9276
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9276
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8827
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8827
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8778
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8778
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8699
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8699
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8644
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8644
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8563
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8563
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8305
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8305
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8293
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8293
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8257
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8257
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8237
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8211
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8211
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8128
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8128
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8081
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8081
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7991
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7991
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7959
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7959
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7958
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7958
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7915
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7915
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7886
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7886
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7882
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7882
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7861
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7861
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7728
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7728
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7716
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7716
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7654
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7654
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7585
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7585
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7570
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7570
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7553
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7553
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7548
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7548
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7547
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7547
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7543
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7543
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7451
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7451
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7438
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7438
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7385
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7385
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7336
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7336
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7324
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7324
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7307
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7307
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7305
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7305
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7273
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7273
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7259
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7259
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7257
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7257
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7220
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7220
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7208
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7195
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7195
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7184
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7184
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7154
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7154
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7145
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7145
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7145
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7145
Calcium-dependent protein kinase CDPK3 Q3HNM6 Q3HNM6_TOXGO Toxoplasma gondii 5 0.7131
Calcium-dependent protein kinase CDPK3 Q3HNM6 Q3HNM6_TOXGO Toxoplasma gondii 5 0.7131
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 4 0.7115
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7115
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7115
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 4 0.7115
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7078
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7078
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7073
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7073
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7066
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7066
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7063
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7063
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7048
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7048
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7043
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7043
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7028
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7028
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7002
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7002

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