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

2,3',4,5',6-pentahydroxybenzophenone 2-O-(4''-acetyl)-beta-D-xylopyranoside

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2,3',4,5',6-pentahydroxybenzophenone 2-O-(4''-acetyl)-beta-D-xylopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzophenone Glycoside
Canonical Smiles CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)Oc1cc(O)cc(c1C(=O)c1cc(O)cc(c1)O)O
InChI InChI=1S/C20H20O11/c1-8(21)30-15-7-29-20(19(28)18(15)27)31-14-6-12(24)5-13(25)16(14)17(26)9-2-10(22)4-11(23)3-9/h2-6,15,18-20,22-25,27-28H,7H2,1H3/t15-,18+,19-,20+/m1/s1
InChIKey IFQTWVGHIGUIEQ-NMLACTOBSA-N
Formula C20H20O11
HBA 11
HBD 6
MW 436.37
Rotatable Bonds 5
TPSA 183.21
LogP 0.13
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 436.1
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: 42603669
Nmrshiftdb2: 60079757

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 436.37 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 436.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.35
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
68.1
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.68
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.03
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.96
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.28
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
-25.65
Rat (Acute)
2.31
Rat (Chronic Oral)
3.62
Fathead Minnow
3.89
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
555.68
Hydration Free Energy
-9.44
Log(D) at pH=7.4
0.54
Log(P)
0.69
Log S
-4.48
Log(Vapor Pressure)
-9.49
Melting Point
188.65
pKa Acid
6.15
pKa Basic
4.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8774
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8774
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8105
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8105
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8096
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8096
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8084
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8084
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7988
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7988
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7980
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7980
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7853
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7853
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7718
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7718
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7705
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7705
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7465
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7465
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7387
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7387
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7295
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7295
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 4 0.7270
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 4 0.7270
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7269
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7269
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7267
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7267
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7192
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7192
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7170
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7170
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7127
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7127
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7116
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7116
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7037
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7037
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7033
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7033
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7022
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7022

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