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1-O-p-hydroxybenzoyl-beta-D-glucopyranoside

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

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C13H16O8/c14-5-8-9(16)10(17)11(18)13(20-8)21-12(19)6-1-3-7(15)4-2-6/h1-4,8-11,13-18H,5H2/t8-,9-,10+,11-,13+/m1/s1
InChIKey	XWTGDGASXRARSP-HMUNZLOLSA-N
Formula	C₁₃H₁₆O₈
HBA	8
HBD	5
MW	300.26
Rotatable Bonds	3
TPSA	136.68
LogP	-1.65
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	300.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tabebuia argentea	Bignoniaceae	Plantae	3350745
2	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]
De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]

Pubchem: 14132342

Cas: 25545-07-7

Zinc: ZINC000013507869

Chebi: 145301

Nmrshiftdb2: 60024843

Metabolights: MTBLC145301

Chembl: CHEMBL482044

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 300.26 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 300.26 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.26 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -5.41
Human Oral Bioavailability 20%: 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: -1.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.4
Plasma Protein Binding: 55.18
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: 7.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.08
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.91
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 3.65
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: -1.46
Rat (Acute): 1.88
Rat (Chronic Oral): 3.35
Fathead Minnow: 3.81
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: 421.28
Hydration Free Energy: -15.28
Log(D) at pH=7.4: -0.73
Log(P): -0.78
Log S: -1.5
Log(Vapor Pressure): -10.18
Melting Point: 166.2
pKa Acid: 5.12
pKa Basic: 4.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8917
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8917
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8753
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8753
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8675
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8675
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8657
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8657
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8368
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8368
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8315
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8315
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8251
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8251
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8231
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8231
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8170
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8170
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8111
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8111
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7988
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7988
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7967
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7967
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7964
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7964
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7892
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7892
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7875
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7875
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	4	0.7871
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	4	0.7871
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7840
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7840
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7779
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7779
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7669
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7669
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7645
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7645
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7625
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7625
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7545
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7545
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7516
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7516
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7515
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7515
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7504
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7504
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7477
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7477
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7475
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7475
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7460
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7460
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7460
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7460
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7456
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7456
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7376
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7376
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7358
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7358
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7355
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7355
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7354
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7354
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7341
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7341
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7335
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7335
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7284
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7284
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7281
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7281
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7254
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7254
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7254
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7254
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7223
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7223
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7194
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7194
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7181
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7181
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7179
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7179
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7173
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7173
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7169
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7169
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7166
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7166
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7162
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7162
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7150
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7150
Glucose-1-phosphate thymidylyltransferase	P26393	RMLA_SALTY	Salmonella typhimurium	3	0.7133
Glucose-1-phosphate thymidylyltransferase	P26393	RMLA_SALTY	Salmonella typhimurium	3	0.7133
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.7118
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.7118
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7111
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7111
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7111
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7111
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7100
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7100
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7094
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7094
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	3	0.7080
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	3	0.7080
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7070
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7070
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7066
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7066
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7046
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7046
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7042
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7042
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7041
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7041
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7034
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7034
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7029
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7029
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7018
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7018
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7014
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7014

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