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4-hydroxybenzyl beta-D-glucopyranoside

Family: Plantae - Cucurbitaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	OC[C@H]1O[C@@H](OCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C13H18O7/c14-5-9-10(16)11(17)12(18)13(20-9)19-6-7-1-3-8(15)4-2-7/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChIKey	WGBHVCJJFIVFAL-UJPOAAIJSA-N
Formula	C₁₃H₁₈O₇
HBA	7
HBD	5
MW	286.28
Rotatable Bonds	4
TPSA	119.61
LogP	-1.29
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	286.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrullus colocynthis	Cucurbitaceae	Plantae	252529

Showing of synonyms

Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]

Pubchem: 49871127

Zinc: ZINC000013514680

Nmrshiftdb2: 60024064

Chembl: CHEMBL3609099

No compound-protein relationship available.

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 286.28 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 286.28 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 286.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.43
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.240
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.630
Plasma Protein Binding: 54.33
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: 7.690
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.480
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.010
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.740
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: -1.460
Rat (Acute): 1.810
Rat (Chronic Oral): 3.310
Fathead Minnow: 3.640
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: 410.560
Hydration Free Energy: -19.350
Log(D) at pH=7.4: -0.460
Log(P): -1.31
Log S: -1.19
Log(Vapor Pressure): -10.67
Melting Point: 169.31
pKa Acid: 7.35
pKa Basic: 4.05

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9364
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9026
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8992
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8939
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8870
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8831
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8719
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8712
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8690
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8646
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8595
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8590
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8588
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8579
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8561
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8542
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8507
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8268
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	4	0.8253
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8213
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8183
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.8161
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8132
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.8118
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8082
tRNA(Phe) (4-demethylwyosine(37)-C(7)) aminocarboxypropyltransferase	O58523	TYW2_PYRHO	Pyrococcus horikoshii	3	0.7993
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7986
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7952
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7936
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7916
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7845
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7822
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7813
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7698
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7692
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7691
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7673
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7584
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7529
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7524
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7489
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7472
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7439
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7435
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7433
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7411
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.7383
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7360
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7349
Beta-glucosidase	Q8T0W7	Q8T0W7_9NEOP	Neotermes koshunensis	3	0.7341
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7336
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7328
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7292
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7292
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7280
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7280
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7270
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7268
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7266
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7255
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7246
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	4	0.7241
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7232
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7230
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7212
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7201
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7197
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7196
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	4	0.7193
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7171
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7169
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7160
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7157
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7157
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7152
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7147
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7135
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7086
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7079
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7055
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7047
Raucaffricine-O-beta-D-glucosidase	Q9SPP9	RG1_RAUSE	Rauvolfia serpentina	3	0.7046
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7043
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7043
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7039
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7032
Methionine--tRNA ligase	P00959	SYM_ECOLI	Escherichia coli	3	0.7028
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7013
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7006
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7005
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7004

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