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Taxiphyllin 6-O-gallate

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Cyanogenic Glucoside

Canonical Smiles	c1(c(c(cc(c1)C(=O)OCC1C(C(C(C(O1)O[C@H](c1ccc(cc1)O)C#N)O)O)O)O)O)O
InChI	InChI=1S/C21H21NO11/c22-7-14(9-1-3-11(23)4-2-9)32-21-19(29)18(28)17(27)15(33-21)8-31-20(30)10-5-12(24)16(26)13(25)6-10/h1-6,14-15,17-19,21,23-29H,8H2/t14-,15?,17?,18?,19?,21?/m0/s1
InChIKey	FRFAGOXEXBHECU-NDYOKGLISA-N
Formula	C₂₁H₂₁NO₁₁
HBA	12
HBD	7
MW	463.4
Rotatable Bonds	6
TPSA	210.16
LogP	-0.25
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	463.11
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Syzygium samarangense	Myrtaceae	Plantae	260143

Showing of synonyms

Samy M.N, Sugimoto S, et al. (2014). Taxiphyllin 6-O-Gallate, Actinidioionoside 6-O-Gallate and Myricetrin 2-O-Sulfate from the Leaves of Syzygium samarangense and Their Biological Activities. Chemical & pharmaceutical bulletin,2014, 62(10), 1013-8. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OCc3ccccc3

Level: 2

Mol. Weight: 463.4 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 463.4 g/mol

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 463.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 463.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 463.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.49
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 20.1
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 13.29
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.5
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.48
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: -87.67
Rat (Acute): 2.37
Rat (Chronic Oral): 3.83
Fathead Minnow: 4.16
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 583.66
Hydration Free Energy: -4.03
Log(D) at pH=7.4: 0.42
Log(P): -0.06
Log S: -3.96
Log(Vapor Pressure): -11.01
Melting Point: 191.61
pKa Acid: 5.61
pKa Basic: 4.91

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9408
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9322
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9101
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9035
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8868
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8804
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8737
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8667
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8636
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8560
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8556
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8521
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8505
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8504
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8471
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8466
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8441
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8382
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8374
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8326
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8315
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8278
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8264
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8246
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8186
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8178
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8176
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8174
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8144
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8093
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8076
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8057
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8051
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7972
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7969
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7968
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7938
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7900
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7840
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7835
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7780
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7764
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7754
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7737
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7734
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7714
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7669
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7652
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7589
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7560
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7542
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7523
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7518
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7464
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7460
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7427
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7423
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7419
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7411
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7405
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7398
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7313
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7306
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7291
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7289
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7283
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7263
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7261
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7260
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7240
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7232
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7220
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7215
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7209
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7208
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7203
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7194
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7193
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7175
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7164
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7164
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7160
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7158
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7152
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7101
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7095
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7091
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7089
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7085
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7074
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7067
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	5	0.7040
Thymidylate synthase	Q8NS38	TYSY_CORGL	Corynebacterium glutamicum	5	0.7038
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7031
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7010
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7009
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7008

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