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2,3',4,5',6-pentahydroxybenzophenone 4-O-beta-D-glucopyranoside

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Benzophenone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2)O)C(=O)c2cc(O)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C19H20O11/c20-6-13-16(26)17(27)18(28)19(30-13)29-10-4-11(23)14(12(24)5-10)15(25)7-1-8(21)3-9(22)2-7/h1-5,13,16-24,26-28H,6H2/t13-,16-,17+,18-,19-/m1/s1
InChIKey	SILOTFUKVQVHLR-LQDZTQBFSA-N
Formula	C₁₉H₂₀O₁₁
HBA	11
HBD	8
MW	424.36
Rotatable Bonds	5
TPSA	197.37
LogP	-1.08
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	424.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum humifusum	Hypericaceae	Plantae	626746

Showing of synonyms

Rouis Z, Abid N, et al. (2013). Benzophenone glycosides from Hypericum humifusum ssp. austral. Journal of Natural Products,2013,76(5),979-982. [View] [PubMed]

Pubchem: 71712664

Zinc: ZINC000205748565

Nmrshiftdb2: 70071270

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)c2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 424.36 g/mol

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 424.36 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 424.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 424.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.74
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.870
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.580
Plasma Protein Binding: 66.33
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: 12.830
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.700
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.680
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.420
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: -18.970
Rat (Acute): 2.290
Rat (Chronic Oral): 4.150
Fathead Minnow: 3.590
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: 602.830
Hydration Free Energy: -12.050
Log(D) at pH=7.4: -0.670
Log(P): -0.58
Log S: -3.16
Log(Vapor Pressure): -11.83
Melting Point: 192.13
pKa Acid: 4.78
pKa Basic: 7.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9250
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9250
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.9190
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.9190
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9125
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9125
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8952
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8952
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8841
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8841
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8773
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8773
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8563
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8563
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8479
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8479
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8475
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8475
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8378
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8378
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8353
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8353
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8274
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8274
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8238
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8238
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8220
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8220
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8134
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8134
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8007
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8007
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7936
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7936
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7915
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7915
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7868
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7868
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7796
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7796
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7723
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7723
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7704
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7704
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7693
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7693
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7665
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7665
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7596
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7596
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7583
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7583
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7577
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7577
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7567
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7567
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	3	0.7490
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	3	0.7490
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7443
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7443
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7386
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7386
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7355
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7355
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7351
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7351
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7241
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7241
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7228
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7228
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7225
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7225
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7197
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7197
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7194
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7194
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7186
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7186
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7183
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7183
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7175
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7175
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7132
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7132
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7130
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7130
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7123
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7123
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7116
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7116
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7080
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7080
Aurora kinase B-A	Q6DE08	AUKBA_XENLA	Xenopus laevis	3	0.7057
Aurora kinase B-A	Q6DE08	AUKBA_XENLA	Xenopus laevis	3	0.7057
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7057
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7057
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7054
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7054
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7052
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7052
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7041
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7041
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7036
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7036
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7027
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7027
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7021
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7021
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7020
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7020
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7019
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7019
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7010
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7010
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7002
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7002

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