Benzoic acid, p-(beta-D-glucopyranosyloxy)-methyl ester - Compound Card

Benzoic acid, p-(beta-D-glucopyranosyloxy)-methyl ester

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Benzoic acid, p-(beta-D-glucopyranosyloxy)-methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Benzenoid
Canonical Smiles OCC1OC(Oc2ccc(cc2)C(=O)OC)C(C(C1O)O)O
InChI InChI=1S/C14H18O8/c1-20-13(19)7-2-4-8(5-3-7)21-14-12(18)11(17)10(16)9(6-15)22-14/h2-5,9-12,14-18H,6H2,1H3
InChIKey IZEJPIRXGMAQFL-UHFFFAOYSA-N
Formula C14H18O8
HBA 8
HBD 4
MW 314.29
Rotatable Bonds 4
TPSA 125.68
LogP -1.35
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 314.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Mohamed T.A, Abd El Aty A.A, et al. (2021). New antimicrobial metabolites from the medicinal herb Artemisia herba-Alba. Natural product research, 2021, 35(12), 1959-1967. [View] [PubMed]
Pubchem: 56667665

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 314.29 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 314.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.29
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
-1.45
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
5.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.06
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.38
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.4
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
2.08
Rat (Acute)
1.86
Rat (Chronic Oral)
3.44
Fathead Minnow
3.98
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
402.9
Hydration Free Energy
-15.85
Log(D) at pH=7.4
-0.11
Log(P)
-0.21
Log S
-1.49
Log(Vapor Pressure)
-8.88
Melting Point
164.99
pKa Acid
6.38
pKa Basic
2.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9225
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9082
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8685
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8549
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8545
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8334
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8309
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8168
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.8075
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8048
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8048
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8045
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8008
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7992
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7942
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7850
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7845
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7811
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7772
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7740
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7731
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7643
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7601
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7568
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7566
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7553
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7396
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7381
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7355
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7325
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7322
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7294
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7245
Galactoside O-acetyltransferase P07464 THGA_ECOLI Escherichia coli 4 0.7239
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7210
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7210
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7209
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7208
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7205
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7180
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7177
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7162
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7153
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7126
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7098
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7089
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 3 0.7081
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7068
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7068
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7057
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7038
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 2 0.7021
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7017
DNA adenine methylase P0AEE8 DMA_ECOLI Escherichia coli 4 0.7003

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