Maltol 3-O-[6-O-benzoyl]-beta-D-glucopyranoside - Compound Card

Maltol 3-O-[6-O-benzoyl]-beta-D-glucopyranoside

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Maltol 3-O-[6-O-benzoyl]-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O[C@@H]1C(COCC(=O)c2ccccc2)O[C@H]([C@H](C1O)O)Oc1c(C)occc1=O
InChI InChI=1S/C20H22O9/c1-11-19(13(21)7-8-27-11)29-20-18(25)17(24)16(23)15(28-20)10-26-9-14(22)12-5-3-2-4-6-12/h2-8,15-18,20,23-25H,9-10H2,1H3/t15?,16-,17?,18+,20+/m1/s1
InChIKey BWUODXRXWQHUNT-PVSAOXIISA-N
Formula C20H22O9
HBA 9
HBD 3
MW 406.39
Rotatable Bonds 7
TPSA 135.66
LogP 0.03
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 406.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Silene arenarioides Caryophyllaceae Plantae 1937741

Showing of synonyms

  • Golea L, Benkhaled M, et al. (2017). Phytochemical components and biological activities of Silene arenarioides Desf.. Natural product research, 2017, 31(23), 2801-2805. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)COCC2CCCC(O2)Oc3c(=O)ccoc3

Level: 2

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1ccccc1C(=O)COCC2CCCCO2

Level: 1

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1occc(=O)c1OC2CCCCO2

Level: 1

Mol. Weight: 406.39 g/mol

Structure

SMILES: O=c1ccocc1

Level: 0

Mol. Weight: 406.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 406.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.08
Plasma Protein Binding
73.19
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
4.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.43
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
-16.01
Rat (Acute)
2.88
Rat (Chronic Oral)
3.34
Fathead Minnow
4.12
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
454.64
Hydration Free Energy
-9.13
Log(D) at pH=7.4
0.37
Log(P)
-0.64
Log S
-1.95
Log(Vapor Pressure)
-10.13
Melting Point
179.12
pKa Acid
5.4
pKa Basic
3.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9426
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9162
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8766
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8650
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8358
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.8326
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8293
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8229
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.8054
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.8051
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8046
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8014
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7982
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7950
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7901
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7894
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7892
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7846
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7785
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7743
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7683
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7652
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7613
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7611
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7607
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7479
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7449
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7438
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7437
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7436
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7406
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7405
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7404
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7384
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7363
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7358
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7351
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7328
Methionine--tRNA ligase P00959 SYM_ECOLI Escherichia coli 3 0.7321
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7300
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7282
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7263
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7186
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7123
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7100
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7097
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7059
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7052
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7039
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7017
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7017
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7016
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7004

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