2,3',4,5',6-pentahydroxybenzophenone 4-O-(6''-benzoyl)-beta-D-glucopyranoside - Compound Card

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

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

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzophenone Glycoside
Canonical Smiles Oc1cc(O)cc(c1)C(=O)c1c(O)cc(cc1O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C26H24O12/c27-14-6-13(7-15(28)8-14)21(31)20-17(29)9-16(10-18(20)30)37-26-24(34)23(33)22(32)19(38-26)11-36-25(35)12-4-2-1-3-5-12/h1-10,19,22-24,26-30,32-34H,11H2/t19-,22-,23+,24-,26-/m1/s1
InChIKey KMLCBJWFZDXLFN-BFEIJTHESA-N
Formula C26H24O12
HBA 12
HBD 7
MW 528.47
Rotatable Bonds 7
TPSA 203.44
LogP 0.78
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 528.13
Number of Lipinski Rule Violations 3
# 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: 71712663
Nmrshiftdb2: 70071269

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2ccc(cc2)OC(O3)CCCC3COC(=O)c4ccccc4

Level: 3

Mol. Weight: 528.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 528.47 g/mol

Structure

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

Level: 2

Mol. Weight: 528.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 528.47 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 528.47 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 528.47 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 528.47 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 528.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.41
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
77.23
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
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
10.43
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.77
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
-1209.8
Rat (Acute)
2.43
Rat (Chronic Oral)
3.9
Fathead Minnow
4.82
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
601.2
Hydration Free Energy
-3.17
Log(D) at pH=7.4
1.46
Log(P)
1.82
Log S
-5.29
Log(Vapor Pressure)
-10.31
Melting Point
199.06
pKa Acid
5.89
pKa Basic
4.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9599
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9599
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9222
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9222
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9108
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9108
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9018
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9018
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8782
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8782
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8746
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8746
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8701
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8701
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8688
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8688
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8630
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8630
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8625
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8625
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8604
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8604
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8501
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8501
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8484
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8484
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8472
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8472
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8467
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8467
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8385
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8385
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8376
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8376
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8348
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8348
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8259
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8259
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8257
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8257
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8143
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8143
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8142
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8142
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.8068
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.8068
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8034
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8034
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8032
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8032
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7767
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7767
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7749
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7749
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7711
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7711
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7683
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7683
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7659
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7659
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7653
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7653
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7642
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7642
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7588
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7588
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7587
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7587
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7569
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7569
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7554
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7554
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7516
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7516
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7514
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7514
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7513
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7513
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7480
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7480
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7430
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7430
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7420
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7420
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7415
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7415
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7377
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7377
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7369
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7369
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 2 0.7361
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 2 0.7361
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7354
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7354
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7350
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7350
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7343
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7343
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7326
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7326
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7317
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7317
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7290
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7290
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7289
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7289
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7282
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7282
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7253
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7253
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7251
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7251
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7244
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7244
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7236
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7236
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7236
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7236
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7233
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7233
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7225
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7225
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7206
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7206
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7199
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7199
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7190
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7190
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7178
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7178
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7167
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7167
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7165
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7165
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7150
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7150
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7146
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7146
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7127
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7127
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7126
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7126
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7116
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7116
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7105
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7105
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7099
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7099
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7088
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7088
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7061
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7061
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7037
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7037
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7025
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7025
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7017
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7017
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7014
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7014
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7003
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7003

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