4-(beta-D-glucopyranosyloxy)benzaldehyde - Compound Card

4-(beta-D-glucopyranosyloxy)benzaldehyde

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4-(beta-D-glucopyranosyloxy)benzaldehyde

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@H]1O[C@@H](Oc2ccc(cc2)C=O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11+,12-,13-/m1/s1
InChIKey OLZAGZCCJJBKNZ-UJPOAAIJSA-N
Formula C13H16O7
HBA 7
HBD 4
MW 284.26
Rotatable Bonds 4
TPSA 116.45
LogP -1.32
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 284.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrullus colocynthis Cucurbitaceae Plantae 252529

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]
Pubchem: 7573800
Nmrshiftdb2: 60030127
Bindingdb: 50245886
CPRiL: 891
Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 284.26 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 284.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 284.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.420
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
46.94
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
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
4.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.210
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.440
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.090
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
-1.730
Rat (Acute)
1.930
Rat (Chronic Oral)
2.960
Fathead Minnow
3.650
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
400.610
Hydration Free Energy
-18.480
Log(D) at pH=7.4
-0.570
Log(P)
-1.08
Log S
-1.1
Log(Vapor Pressure)
-10.96
Melting Point
170.15
pKa Acid
6.46
pKa Basic
3.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8701
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8644
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8603
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8435
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8355
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8263
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8242
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8208
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8201
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8140
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8095
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.8053
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8049
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8047
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.8034
Galactoside O-acetyltransferase P07464 THGA_ECOLI Escherichia coli 4 0.8007
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7888
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7842
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7819
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7809
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7786
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7752
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7722
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7690
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7662
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7658
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7581
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7550
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7488
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7465
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7443
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7415
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7404
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7352
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7333
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7330
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7316
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7284
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7270
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7266
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7261
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7249
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7243
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7224
Alpha-aminoadipic semialdehyde dehydrogenase P49419 AL7A1_HUMAN Homo sapiens 3 0.7209
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7201
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7190
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7178
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7151
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7147
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7141
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7136
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7119
Retinal dehydrogenase 2 O94788 AL1A2_HUMAN Homo sapiens 3 0.7105
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7103
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7094
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7078
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7078
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7059
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7021
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7018
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7001

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