(+)-gallocatechin - Compound Card

(+)-gallocatechin

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(+)-gallocatechin

Structure
Zoomed Structure
  • Family: Plantae - Rosaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Aglycone
Canonical Smiles Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@H](Cc2c(c1)O)O
InChI InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1
InChIKey XMOCLSLCDHWDHP-SWLSCSKDSA-N
Formula C15H14O7
HBA 7
HBD 6
MW 306.27
Rotatable Bonds 1
TPSA 130.61
LogP 1.25
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 306.07
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Quercus suber Fagaceae Plantae 58331
2 Limoniastrum guyonianum Plumbaginaceae Plantae 114145
3 Parkia biglobosa Leguminosae/Fabaceae Plantae 889930
4 Helianthemum getulum Cistaceae Plantae 2020754
5 Rosmarinuseriocalyx Lamiaceae Plantae
6 Rosa canina Rosaceae Plantae 74635

Showing of synonyms

  • Kuete V, Sipowo Tala VR, et al. (2018). Catechin Derivatives from Parkia biglobosa Displayed Selective Cytotoxicity Towards Leukemia CCRF-CEM Cell Line and its P-Glycoprotein Expressing Subline CEM/ADR5000. Investigational Medicinal Chemistry and Pharmacology, (2018), 1(1),2. [View]
  • Fetni S, Bertella N, et al. (2020). Composition and biological activity of the Algerian plant Rosa canina L by HPLC-UV-MS. Arabian Journal of Chemistry, 2020, 13(1), 1105-1119. [View]
  • Ito H, Yamaguchi K, et al. (2002). Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber. Journal of Natural Products,2002,65(3),339-345. [View] [PubMed]
  • Terfassi S, Dauvergne X, et al. (2022). First report on phytochemical investigation, antioxidant and antidiabetic activities of Helianthemum getulum. Natural product research, 2022, 36(11), 2806-2813. [View] [PubMed]
  • Trabelsi N, Oueslati S, et al. (2013). Phenolic contents and biological activities of Limoniastrum guyonianum fractions obtained by Centrifugal Partition Chromatography. Industrial Crops and Products,2013,49,740-746. [View]
  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
Pubchem: 65084
Kegg Ligand: C12127
Chebi: 31018
Nmrshiftdb2: 60021294
Metabolights: MTBLC31018
Bindingdb: 50135165
CPRiL: 3433
Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 306.27 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 306.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 306.27 g/mol

Antioxidant
Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp)
-6.75
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.380
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.590
Plasma Protein Binding
84.52
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
14.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.970
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.600
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
2.090
Rat (Acute)
2.160
Rat (Chronic Oral)
3.350
Fathead Minnow
3.880
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
499.040
Hydration Free Energy
-11.980
Log(D) at pH=7.4
0.870
Log(P)
0.29
Log S
-2.11
Log(Vapor Pressure)
-8.96
Melting Point
246.02
pKa Acid
6.09
pKa Basic
7.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9288
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9288
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9071
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9071
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9026
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9026
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8815
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8815
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8764
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8764
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8491
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8491
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8458
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8458
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8426
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8426
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8289
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8289
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8285
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8247
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8247
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8238
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8238
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8217
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8172
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8172
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8144
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8144
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8113
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8113
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8110
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8110
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8095
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8095
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8062
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8062
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8048
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8048
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7951
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7951
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7922
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7922
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7913
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7913
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7910
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7910
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7832
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7832
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7778
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7778
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7711
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7711
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7693
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7693
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7673
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7673
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7657
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7657
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7582
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7582
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7581
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7581
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7552
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7552
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7543
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7543
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7533
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7533
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7514
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7514
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7477
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7477
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7441
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7441
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 4 0.7415
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 4 0.7415
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7400
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7400
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7399
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7399
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7390
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7390
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7386
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7386
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7375
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7375
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7364
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7364
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7329
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7329
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7295
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7295
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7284
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7284
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7250
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7250
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7245
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7245
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7238
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7238
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7215
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7215
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7196
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7196
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7177
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7177
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7171
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7171
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 4 0.7163
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 4 0.7163
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7142
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7142
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7140
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7140
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7132
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7132
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7120
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7120
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7087
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7087
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7077
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7077
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7062
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7062
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7049
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7049
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7040
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7022
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7007
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7007

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