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Myrciaphenone A

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C14H18O9/c1-5(16)10-7(18)2-6(17)3-8(10)22-14-13(21)12(20)11(19)9(4-15)23-14/h2-3,9,11-15,17-21H,4H2,1H3/t9-,11-,12+,13-,14-/m1/s1
InChIKey	GFKQVLKFPJGJEP-RGCYKPLRSA-N
Formula	C₁₄H₁₈O₉
HBA	9
HBD	6
MW	330.29
Rotatable Bonds	4
TPSA	156.91
LogP	-1.52
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	330.1
Number of Lipinski Rule Violations	1

#	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]

Pubchem: 179470

Cas: 26089-54-3

Zinc: ZINC000005167512

Nmrshiftdb2: 60030726

No compound-protein relationship available.

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 330.29 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 330.29 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.0
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.500
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.500
Plasma Protein Binding: 57.26
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: 8.920
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.400
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.880
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.710
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: -0.910
Rat (Acute): 1.900
Rat (Chronic Oral): 3.970
Fathead Minnow: 3.470
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 479.040
Hydration Free Energy: -15.980
Log(D) at pH=7.4: -0.570
Log(P): -0.85
Log S: -2.02
Log(Vapor Pressure): -10.83
Melting Point: 163.45
pKa Acid: 4.98
pKa Basic: 6.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9335
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9199
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.9179
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9148
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9047
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8953
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8851
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8826
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8810
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8771
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8691
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8560
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.8522
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8487
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8231
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8196
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8169
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8085
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8069
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8032
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7923
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7915
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7877
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7873
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7817
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7756
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7744
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7743
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7724
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7653
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7650
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7602
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7553
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7537
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7502
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7466
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7438
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7407
Metallophosphoesterase MPPED2	B1WBP0	MPPD2_RAT	Rattus norvegicus	4	0.7398
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7391
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7365
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7351
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7332
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7311
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7285
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7276
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7268
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7250
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7238
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.7204
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7182
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7179
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7167
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7165
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7153
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7142
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7118
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7084
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7069
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7068
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7064
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7051
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7025
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7015
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	3	0.7011
Nucleoside diphosphate kinase	O58429	NDK_PYRHO	Pyrococcus horikoshii	4	0.7008
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7008

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