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Catechin-3-O-gallate

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol

Canonical Smiles	Oc1cc2O[C@H](c3ccc(c(c3)OC(=O)c3cc(O)c(c(c3)O)O)O)[C@H](Cc2c(c1)O)O
InChI	InChI=1S/C22H18O10/c23-11-6-14(25)12-8-17(28)21(31-18(12)7-11)9-1-2-13(24)19(5-9)32-22(30)10-3-15(26)20(29)16(27)4-10/h1-7,17,21,23-29H,8H2/t17-,21+/m0/s1
InChIKey	GNXIIYFUGQWDJG-LAUBAEHRSA-N
Formula	C₂₂H₁₈O₁₀
HBA	10
HBD	7
MW	442.38
Rotatable Bonds	3
TPSA	177.14
LogP	2.18
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.14
Exact Mass	442.09
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Acacia nilotica	Leguminosae/Fabaceae	Plantae	138033

Showing of synonyms

Omara E.A, Nada S.A, et al. (2012). Therapeutic effect of Acacia nilotica pods extract on streptozotocin induced diabetic nephropathy in rat. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2012, 19(12), 1059-67. [View] [PubMed]

Pubchem: 44257105

Cas: 110801-35-9

Zinc: ZINC000014642828

Nmrshiftdb2: 60028957

Chembl: CHEMBL4763672

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)Oc(ccc2)cc2C(CC3)Oc(c34)cccc4

Level: 2

Mol. Weight: 442.38 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 442.38 g/mol

SMILES: c1ccccc1C(=O)Oc2ccccc2

Level: 1

Mol. Weight: 442.38 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 442.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 442.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -7.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.460
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 89.77
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.870
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.260
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.500
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: -63.620
Rat (Acute): 2.420
Rat (Chronic Oral): 3.560
Fathead Minnow: 4.000
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 614.330
Hydration Free Energy: -5.300
Log(D) at pH=7.4: 2.060
Log(P): 1.47
Log S: -4.78
Log(Vapor Pressure): -10.24
Melting Point: 265.28
pKa Acid: 6.29
pKa Basic: 6.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9623
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9397
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9076
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9011
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8976
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8965
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8957
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8857
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8810
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8781
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8656
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8645
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8612
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8530
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8505
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8504
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8501
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	5	0.8499
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8489
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	4	0.8485
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8475
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8460
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8414
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8404
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8361
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8356
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.8347
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8339
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8255
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8203
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8177
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8154
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8140
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8102
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8081
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8081
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8080
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8060
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8017
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7979
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7971
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7948
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7936
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7912
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7906
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7903
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7873
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	4	0.7866
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7865
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7857
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7848
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7830
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7805
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7793
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7786
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7786
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7773
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7750
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7733
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7721
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7721
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7703
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7699
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7695
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7692
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7691
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7687
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7678
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7674
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7659
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7648
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7602
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7600
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7597
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7595
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7594
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7593
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7573
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.7567
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7562
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7559
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7548
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7544
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7540
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7539
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7497
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7480
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	4	0.7477
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7472
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7457
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7455
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	5	0.7449
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7437
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7428
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7402
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	5	0.7384
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7379
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7374
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7369
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7369
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7365
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7360
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7339
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7325
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7307
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7305
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7294
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7289
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7283
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7266
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7260
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7260
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7249
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7246
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7244
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7244
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7241
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7234
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7229
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7228
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7228
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7226
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7192
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7192
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7191
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7164
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7164
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7162
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7154
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7134
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7133
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7132
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7131
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7121
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	4	0.7109
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7107
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7105
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7100
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7099
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.7085
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7084
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7080
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7070
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7055
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7034
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7028
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7026
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7024
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7010

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