(˗)gallocatechin - Compound Card

(˗)gallocatechin

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(˗)gallocatechin

Structure
Zoomed Structure
  • Family: Cistaceae, Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
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+/m1/s1
InChIKey XMOCLSLCDHWDHP-DOMZBBRYSA-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 Helianthemum sessiliflorum Cistaceae Plantae 2650562
2 Euphorbia bupleuroides Euphorbiaceae Plantae 1532838

Showing of synonyms

  • Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
  • Aichour S, Haba H, et al. (2014). Terpenoids and other constituents from Euphorbia bupleuroides. Phytochemistry,2014,10,198-203. [View]
Pubchem: 9882981
Chebi: 71225
Nmrshiftdb2: 60016314
Metabolights: MTBLC71225
Bindingdb: 50373220

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 210.28 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 134.18 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.76
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
-0.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.590
Plasma Protein Binding
83.43
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
14.440
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
4.570
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
2.030
Rat (Acute)
2.170
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
500.080
Hydration Free Energy
-12.000
Log(D) at pH=7.4
0.890
Log(P)
0.36
Log S
-2.12
Log(Vapor Pressure)
-8.91
Melting Point
238.7
pKa Acid
6.14
pKa Basic
7.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9015
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9015
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8927
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8927
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8916
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8916
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8736
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8736
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8638
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8638
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8439
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8439
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8431
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8431
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8402
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8402
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8381
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8381
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8181
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8181
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8079
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8079
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8055
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8055
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.8034
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.8034
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.7945
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.7945
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7926
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7926
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7923
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7923
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7895
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7895
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7885
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7885
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7871
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7871
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7867
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7867
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7855
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7855
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7837
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7837
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7819
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7819
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 4 0.7817
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 4 0.7817
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7764
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7764
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7734
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7734
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7725
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7725
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7720
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7720
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7704
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7704
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7636
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7636
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7597
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7597
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7552
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7552
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7527
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7527
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7515
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7515
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7509
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7509
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7503
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7503
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7480
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7480
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7451
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7451
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7428
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7428
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7417
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7417
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7396
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7396
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7363
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7363
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7348
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7348
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7323
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7323
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7321
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7321
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7318
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7318
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7314
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7314
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7302
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7302
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7286
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7286
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7270
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7270
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7266
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7266
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7259
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7259
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7216
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7216
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7201
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7201
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7195
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7195
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7191
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7191
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7182
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7182
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7177
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7177
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7168
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7168
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7154
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7154
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 4 0.7150
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 4 0.7150
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7147
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7147
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7147
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7147
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7130
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7130
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7126
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7126
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7119
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7119
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7108
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7108
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7105
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7105
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7100
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7097
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7097
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7070
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7070
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7049
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7049
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7044
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7044
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7036
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7036
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7035
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7035
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7021
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7021
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7015
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7015
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7010
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7010
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7002
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7002

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