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Catechin-4-O-gallate

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

Canonical Smiles	Oc1cc2O[C@H](c3ccc(c(c3)O)OC(=O)c3cc(O)c(c(c3)O)O)[C@H](Cc2c(c1)O)O
InChI	InChI=1S/C22H18O10/c23-11-6-13(24)12-8-17(28)21(31-19(12)7-11)9-1-2-18(14(25)3-9)32-22(30)10-4-15(26)20(29)16(27)5-10/h1-7,17,21,23-29H,8H2/t17-,21+/m0/s1
InChIKey	BGMKUBZMMGXFAE-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: 44257106

Cas: 110784-23-1

Zinc: ZINC000014642841

Nmrshiftdb2: 60028958

Chembl: CHEMBL4741553

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)Oc(cc2)ccc2C(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): -7.09
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: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.940
Plasma Protein Binding: 91.96
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: 12.840
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.520
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.280
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.610
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: -63.550
Rat (Acute): 2.410
Rat (Chronic Oral): 3.690
Fathead Minnow: 4.020
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: 612.280
Hydration Free Energy: -5.110
Log(D) at pH=7.4: 1.960
Log(P): 1.66
Log S: -4.87
Log(Vapor Pressure): -10.49
Melting Point: 274.97
pKa Acid: 6.0
pKa Basic: 6.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9737
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9148
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9105
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.9092
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8994
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8988
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8946
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8916
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8883
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.8791
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8736
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8717
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8684
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8684
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8606
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8592
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8519
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8514
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8489
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8488
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8471
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8442
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8402
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8314
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8309
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8304
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8240
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8172
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8165
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8077
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8072
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8034
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8016
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	4	0.8005
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7976
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7973
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7972
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7949
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7947
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7907
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7898
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7893
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7873
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7858
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7847
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7841
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7827
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7769
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7756
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7753
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7751
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7737
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7736
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7721
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7714
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7650
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7647
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7642
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7640
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7620
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7609
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7598
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7592
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7582
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7581
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7564
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7555
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7552
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7552
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7552
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7530
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7519
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7510
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7498
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7484
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7447
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7441
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7434
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7423
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7415
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7412
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7402
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7389
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.7381
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7371
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7370
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7368
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7365
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7360
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7359
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	5	0.7357
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	5	0.7332
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7331
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7325
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7321
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7307
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7302
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7282
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7272
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7268
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7266
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7264
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7254
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7248
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7244
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7227
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7226
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7214
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7213
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7196
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7188
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7175
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7170
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7166
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7160
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7160
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7159
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.7148
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7147
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7147
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7144
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7141
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7139
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7136
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7132
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7129
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7128
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7118
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7106
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7102
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7092
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7082
16S rRNA (adenine(1408)-N(1))-methyltransferase	A8C927	NPMA_ECOLX	Escherichia coli	4	0.7082
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7082
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	4	0.7080
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7069
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	5	0.7064
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7057
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7056
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7053
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7042
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7035
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7031
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7028
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7023
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7019

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