2,3',4,5',6-pentahydroxybenzophenone 2-O-alpha-L-arabinopyranoside - Compound Card

2,3',4,5',6-pentahydroxybenzophenone 2-O-alpha-L-arabinopyranoside

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2,3',4,5',6-pentahydroxybenzophenone 2-O-alpha-L-arabinopyranoside

Structure
Zoomed Structure
  • Family: Hypericaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzophenone Glycoside
Canonical Smiles Oc1cc(O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)c(c(c1)O)C(=O)c1cc(O)cc(c1)O
InChI InChI=1S/C18H18O10/c19-8-1-7(2-9(20)3-8)15(24)14-11(22)4-10(21)5-13(14)28-18-17(26)16(25)12(23)6-27-18/h1-5,12,16-23,25-26H,6H2/t12-,16-,17+,18-/m0/s1
InChIKey JYUMFQAYFIHMCL-BIMQEMHKSA-N
Formula C18H18O10
HBA 10
HBD 7
MW 394.33
Rotatable Bonds 4
TPSA 177.14
LogP -0.44
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 394.09
Number of Lipinski Rule Violations 1
# 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: 71712666
Nmrshiftdb2: 70071268

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 282.34 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 182.22 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 178.23 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
68.64
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.48
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
-6.52
Rat (Acute)
2.28
Rat (Chronic Oral)
3.95
Fathead Minnow
3.78
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
580.88
Hydration Free Energy
-12.75
Log(D) at pH=7.4
-0.23
Log(P)
-0.08
Log S
-2.83
Log(Vapor Pressure)
-10.42
Melting Point
181.69
pKa Acid
5.06
pKa Basic
6.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9294
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9294
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9081
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8822
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8822
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8657
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8657
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7835
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7835
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7831
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7831
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7800
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7800
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7717
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7717
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7541
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7541
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7419
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7419
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7401
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7401
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7394
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7394
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7370
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7370
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7352
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7352
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7318
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7318
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7296
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7296
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7253
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7253
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7218
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7218
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7198
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7198
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7128
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7128
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7105
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7105
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7067
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7067
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7045
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7045

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