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1-feruloyl-beta-D-glucopyranoside

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Hydroxycinnamic Acids

Canonical Smiles	OC[C@@H]1O[C@H](OC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m0/s1
InChIKey	JWRQVQWBNRGGPK-JFMSWFBKSA-N
Formula	C₁₆H₂₀O₉
HBA	9
HBD	5
MW	356.33
Rotatable Bonds	5
TPSA	145.91
LogP	-1.24
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	356.11
Number of Lipinski Rule Violations	0

#	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: 50906375

Zinc: ZINC000198414308

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 356.33 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 356.33 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 356.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.83
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.66
Plasma Protein Binding: 59.78
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: 8.52
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.38
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.98
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.78
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: -1.63
Rat (Acute): 1.93
Rat (Chronic Oral): 3.54
Fathead Minnow: 4.13
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 455.09
Hydration Free Energy: -15.95
Log(D) at pH=7.4: 0.12
Log(P): -0.59
Log S: -2.33
Log(Vapor Pressure): -10.44
Melting Point: 167.44
pKa Acid: 5.31
pKa Basic: 3.6

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	0.9519
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9469
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9125
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8991
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8953
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8814
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8768
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8692
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8690
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8555
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8530
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8414
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8310
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8265
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8260
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8200
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8132
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.8119
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8103
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8082
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8037
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8035
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8035
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8001
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7987
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7913
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7832
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7808
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7794
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7786
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7770
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7724
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7696
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7691
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7647
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7634
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7634
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7589
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7585
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7582
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7575
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7567
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7537
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7529
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7501
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7478
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7446
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7445
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7437
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7426
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7418
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7392
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7385
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7372
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7356
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7356
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7345
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7338
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7335
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7333
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7318
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7317
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	2	0.7309
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7304
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7304
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7303
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7297
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7294
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7283
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7272
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7268
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7247
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7225
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7218
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7216
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7215
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7209
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7201
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7191
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7186
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7183
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7174
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7167
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7159
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7158
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7158
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7145
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7133
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7125
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7125
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7120
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7102
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7088
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7083
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7083
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7083
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	3	0.7073
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7064
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7062
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7060
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7047
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7046
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7032
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7026
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7024
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7016
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7015
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	2	0.7010
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7008
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7003

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