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Gallocatechin

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol

Canonical Smiles	C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)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
InChIKey	XMOCLSLCDHWDHP-UHFFFAOYSA-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	Ziziphus spina-christi	Rhamnaceae	Plantae	264981

Showing of synonyms

Kadioglu O, Jacob S, et al. (2016). Evaluating ancient Egyptian prescriptions today: Anti-inflammatory activity of Ziziphus spina-christi. Phytomedicine : international journal of phytotherapy and phytopharmacology,2016, 23(3), 293-306. [View] [PubMed]

Pubchem: 65084

Cas: 970-73-0

Gnps: CCMSLIB00004681470

Zinc: ZINC000003870338

Kegg Ligand: C12127

Chebi: 31018

Nmrshiftdb2: 60021294

Metabolights: MTBLC31018

Chembl: CHEMBL125743

Bindingdb: 50135165

CPRiL: 3433

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 306.27 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 306.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 306.27 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: -5.38
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): 0.59
Plasma Protein Binding: 60.5
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: 14.44
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.12
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.97
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.59
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: 3.49
Rat (Acute): 2.15
Rat (Chronic Oral): 3.36
Fathead Minnow: 3.91
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: 497.38
Hydration Free Energy: -11.95
Log(D) at pH=7.4: 0.84
Log(P): 0.28
Log S: -2.07
Log(Vapor Pressure): -8.74
Melting Point: 237.88
pKa Acid: 6.09
pKa Basic: 7.31

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9406
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9400
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9388
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9010
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8990
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8893
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8868
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8833
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8755
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8678
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8670
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8578
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8562
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.8504
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8481
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8439
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8413
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8361
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8353
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.8323
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8305
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8299
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.8294
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8294
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8275
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.8268
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8243
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8206
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8191
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8142
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.8121
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8087
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.8083
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8078
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.8075
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8074
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8056
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.8042
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8018
Heat shock protein 75 kDa, mitochondrial	Q12931	TRAP1_HUMAN	Homo sapiens	4	0.7995
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7936
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7935
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7883
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7881
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7880
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7875
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7857
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7837
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7829
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7801
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7794
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7779
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7769
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7767
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.7765
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7744
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7738
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7719
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7719
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7715
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7699
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7687
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7684
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7631
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7628
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7623
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7615
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7603
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7588
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7586
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7578
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7576
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7573
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7568
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7561
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7551
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7549
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7541
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7533
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.7519
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7510
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7501
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7500
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7498
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7497
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7471
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7465
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7465
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7463
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7458
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7423
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7417
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7413
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7412
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7388
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7386
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7379
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7360
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7340
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7333
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7329
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7323
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7316
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7310
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7276
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7267
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7266
Cytochrome P450 2B4	P00178	CP2B4_RABIT	Oryctolagus cuniculus	3	0.7258
Cyclic nucleotide-binding protein	B8FW11	B8FW11_DESHD	Desulfitobacterium hafniense	3	0.7256
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7252
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7246
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7244
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7238
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7231
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7230
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7228
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7225
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7225
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7223
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7215
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7206
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7195
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7186
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7181
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7172
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7171
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7164
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7155
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7143
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7136
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7135
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7114
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7111
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7100
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7097
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7093
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7059
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7052
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7045
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7037
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7034
DNA-(apurinic or apyrimidinic site) lyase	Q97FM4	Q97FM4_CLOAB	Clostridium acetobutylicum	4	0.7008

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