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Beta-D-glucopyranosyl 4-O-beta-D-glucopyranosylbenzoate

Family: Plantae - Cruciferae-Brassicaceea
Kingdom: Plantae
Class: Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)c2ccc(cc2)C2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C19H26O12/c20-5-9-11(22)13(24)15(26)17(29-9)7-1-3-8(4-2-7)18(28)31-19-16(27)14(25)12(23)10(6-21)30-19/h1-4,9-17,19-27H,5-6H2/t9-,10-,11-,12-,13+,14+,15-,16-,17?,19+/m1/s1
InChIKey	FVKIBVYKSWGGPY-JEFSMQFLSA-N
Formula	C₁₉H₂₆O₁₂
HBA	12
HBD	8
MW	446.41
Rotatable Bonds	5
TPSA	206.6
LogP	-3.84
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.63
Exact Mass	446.14
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Moricandia arvensis	Cruciferae-Brassicaceea	Plantae	180540

Showing of synonyms

Braham H, Mighri Z, et al. (2005). Antioxidant phenolic glycosides from Moricandia arvensis. Journal of Natural Products,2005,68(4),517-522. [View]

Pubchem: 162835225

Nmrshiftdb2: 70057289

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)c2ccc(cc2)C3CCCCO3

Level: 2

Mol. Weight: 446.41 g/mol

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 446.41 g/mol

SMILES: c1ccccc1C2CCCCO2

Level: 1

Mol. Weight: 446.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 446.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.41 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.1
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.3
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.59
Plasma Protein Binding: 66.67
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: 4.7
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.64
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.2
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 3.74
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: -42.97
Rat (Acute): 2.12
Rat (Chronic Oral): 4.18
Fathead Minnow: 3.41
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 536.44
Hydration Free Energy: -7.77
Log(D) at pH=7.4: -1.87
Log(P): -2.79
Log S: -1.28
Log(Vapor Pressure): -17.67
Melting Point: 204.29
pKa Acid: 4.34
pKa Basic: 4.87

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8982
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8982
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.8825
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.8825
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8739
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8739
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8680
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8680
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8630
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8630
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8452
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8452
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8452
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8452
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8354
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8354
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8147
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8147
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.8042
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.8042
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8012
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8012
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7885
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7885
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7879
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7879
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7856
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7856
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7797
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7797
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7783
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7783
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7733
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7733
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7730
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7730
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7678
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7678
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7629
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7629
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7563
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7563
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7531
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7531
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7439
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7439
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7274
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7274
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7226
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7226
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7205
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7205
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7139
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7139
Strictosidine-O-beta-D-glucosidase	Q8GU20	SG1_RAUSE	Rauvolfia serpentina	4	0.7105
Strictosidine-O-beta-D-glucosidase	Q8GU20	SG1_RAUSE	Rauvolfia serpentina	4	0.7105

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