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1-O-sinapoyl-beta-D-glucose derivative

Family: Plantae - Convolvulaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Glucosyl Hydroxycinnamic Acid

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)/C=C/c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
InChIKey	XRKBRPFTFKKHEF-DGDBGZAXSA-N
Formula	C₁₇H₂₂O₁₀
HBA	10
HBD	5
MW	386.35
Rotatable Bonds	6
TPSA	155.14
LogP	-1.23
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	386.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ipomoea aquatica	Convolvulaceae	Plantae	89636

Showing of synonyms

Hefny Gad M, Demeyer K, et al. (2021). Cytotoxic, Antioxidant, and Antidiabetic Activities versus UPLC-ESI-QTOF-MS Chemical-Profile Analysis of Ipomoea aquatica Fractions. Planta medica,2021, 87(12-13), 1089-1100. [View] [PubMed]

Pubchem: 5280406

Cas: 78185-48-5

Zinc: ZINC000004095571

Kegg Ligand: C01175

Chebi: 16546

Nmrshiftdb2: 60026655

Metabolights: MTBLC16546

Pdb Ligand: SGS

CPRiL: 419118

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 386.35 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 386.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.7
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.91
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 60.12
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: 7.94
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.42
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.02
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.14
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: -4.64
Rat (Acute): 1.93
Rat (Chronic Oral): 3.67
Fathead Minnow: 4.15
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 473.52
Hydration Free Energy: -14.39
Log(D) at pH=7.4: 0.05
Log(P): -1.22
Log S: -2.46
Log(Vapor Pressure): -10.5
Melting Point: 161.83
pKa Acid: 5.58
pKa Basic: 2.95

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9534
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9474
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9436
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9273
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9106
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9074
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8969
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8841
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	4	0.8818
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8696
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8672
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8665
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8629
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8518
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8482
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.8387
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.8349
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8312
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8253
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8184
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8121
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8118
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8114
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7951
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	4	0.7884
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7837
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7692
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	4	0.7684
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7647
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7631
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7615
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7614
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7609
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7598
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7567
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7543
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7502
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7476
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7427
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7399
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7386
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7366
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7364
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7356
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7354
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7314
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	2	0.7304
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7290
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7280
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7271
NAD-dependent protein deacetylase sirtuin-3, mitochondrial	Q9NTG7	SIR3_HUMAN	Homo sapiens	4	0.7269
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7267
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7265
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7265
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7242
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7235
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7220
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7214
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7183
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7159
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7142
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7139
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7124
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7106
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7100
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7085
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7050
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7049
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7026
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7024
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7015
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7011
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7007

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