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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzophenone Glycoside
Canonical Smiles OC[C@H]1OC(Cc2cc(C)c(c(c2)O)C(=O)c2cc(O)cc(c2)O)[C@@H]([C@H]([C@@H]1OC(=O)c1ccccc1)O)O
InChI InChI=1S/C28H28O10/c1-14-7-15(8-20(32)23(14)24(33)17-10-18(30)12-19(31)11-17)9-21-25(34)26(35)27(22(13-29)37-21)38-28(36)16-5-3-2-4-6-16/h2-8,10-12,21-22,25-27,29-32,34-35H,9,13H2,1H3/t21?,22-,25+,26-,27-/m1/s1
InChIKey QRHKNTQBIRFSIV-FHOXIRBYSA-N
Formula C28H28O10
HBA 10
HBD 6
MW 524.52
Rotatable Bonds 7
TPSA 173.98
LogP 1.59
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 524.17
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: 163020467
Nmrshiftdb2: 70071271

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2ccc(cc2)CC3CCC(CO3)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1C(=O)OC(CO2)CCC2Cc3ccccc3

Level: 2

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccc(cc2)CC3CCCCO3

Level: 2

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 524.52 g/mol

Structure

SMILES: O1CCCCC1Cc2ccccc2

Level: 1

Mol. Weight: 524.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 524.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.070
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
85.79
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.860
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.590
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
-1237.060
Rat (Acute)
2.390
Rat (Chronic Oral)
3.790
Fathead Minnow
5.700
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
553.380
Hydration Free Energy
-3.060
Log(D) at pH=7.4
2.160
Log(P)
2.49
Log S
-5.05
Log(Vapor Pressure)
-10.19
Melting Point
195.6
pKa Acid
6.0
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9163
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9163
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9097
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9097
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8946
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8946
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8924
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8924
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8749
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8749
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8716
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8716
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8527
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8527
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8488
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8488
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8462
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8462
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8415
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8415
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8289
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8289
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8276
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8276
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8258
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8258
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8162
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8162
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8154
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8154
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8078
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8078
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8070
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8070
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8029
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8029
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8006
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8006
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7991
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7991
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7984
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7984
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7942
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7942
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7936
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7936
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7828
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7828
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7772
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7772
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7749
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7749
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7741
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7741
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7694
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7694
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7687
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7687
Thymidylate kinase Q8I4S1 Q8I4S1_PLAF7 Plasmodium falciparum 4 0.7686
Thymidylate kinase Q8I4S1 Q8I4S1_PLAF7 Plasmodium falciparum 4 0.7686
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7659
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7659
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7612
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7612
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7570
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7570
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7562
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7562
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7546
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7546
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7536
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7536
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7527
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7527
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7478
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7478
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7467
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7467
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7465
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7465
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7459
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7459
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7452
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7452
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7436
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7436
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7376
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7376
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7375
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7375
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7365
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7365
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7355
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7355
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7348
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7321
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7321
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7292
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7292
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7287
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7287
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7271
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7271
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7263
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7263
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7262
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7262
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7230
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7230
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7215
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7215
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7204
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7204
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7197
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7197
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7195
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7195
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7167
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7167
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7165
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7165
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7154
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7154
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7136
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7136
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7132
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7132
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7125
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7125
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7121
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7121
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7119
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7119
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7109
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7109
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7100
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7100
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7100
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7100
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7079
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7079
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7073
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7073
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7057
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7057
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7038
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7038
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7017
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7017
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7017
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7017
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7004
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7004

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