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Phloroglucinol-1-O-beta-D-glucopyranoside

Family: Plantae - Celastraceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C12H16O8/c13-4-8-9(16)10(17)11(18)12(20-8)19-7-2-5(14)1-6(15)3-7/h1-3,8-18H,4H2/t8-,9-,10+,11-,12-/m1/s1
InChIKey	WXTPOHDTGNYFSB-RMPHRYRLSA-N
Formula	C₁₂H₁₆O₈
HBA	8
HBD	6
MW	288.25
Rotatable Bonds	3
TPSA	139.84
LogP	-1.72
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	288.08
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Maytenus senegalensis	Celastraceae	Plantae	256095

Showing of synonyms

Hussein G, Miyashiro H, et al. (1999). Inhibitory effects of Sudanese plant extracts on HIV-1 replication and HIV-1 protease. Phytotherapy Research,1999,13(1),31-36. [View] [PubMed]

Pubchem: 476785

Cas: 28217-60-9

Gnps: CCMSLIB00005467718

Zinc: ZINC000006524447

Nmrshiftdb2: 60026760

CPRiL: 103041

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 288.25 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 288.25 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 288.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.79
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.150
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.56

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.490
Plasma Protein Binding: 53.26
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: 11.170
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.500
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.740
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.550
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: -1.280
Rat (Acute): 1.640
Rat (Chronic Oral): 3.640
Fathead Minnow: 3.490
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: 449.960
Hydration Free Energy: -17.390
Log(D) at pH=7.4: -1.170
Log(P): -1.81
Log S: -1.43
Log(Vapor Pressure): -10.56
Melting Point: 181.39
pKa Acid: 6.34
pKa Basic: 5.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9256
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9256
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8977
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8977
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8681
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8681
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8444
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8444
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8199
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8199
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8195
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8195
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8182
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8182
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8139
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8139
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8088
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8088
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8060
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8060
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7992
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7992
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7977
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7977
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7851
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7851
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7847
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7847
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7837
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7837
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7771
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7771
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7766
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7766
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7698
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7698
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7592
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7592
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7501
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7501
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7470
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7470
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7442
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7442
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7415
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7415
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7407
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7407
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7350
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7350
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7346
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7346
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7345
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7345
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7344
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7344
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7338
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7338
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7280
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7280
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	3	0.7219
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	3	0.7219
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7211
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7211
Adenylosuccinate synthetase, chloroplastic	Q96529	PURA_ARATH	Arabidopsis thaliana	4	0.7206
Adenylosuccinate synthetase, chloroplastic	Q96529	PURA_ARATH	Arabidopsis thaliana	4	0.7206
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7132
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7132
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7116
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7116
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7107
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7107
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7022
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7022

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