1-O-caffeoyl-beta-D-glucopyranoside - Compound Card

1-O-caffeoyl-beta-D-glucopyranoside

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1-O-caffeoyl-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Potamogetonaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(23-10)24-11(19)4-2-7-1-3-8(17)9(18)5-7/h1-5,10,12-18,20-22H,6H2/b4-2+/t10-,12-,13+,14-,15+/m1/s1
InChIKey WQSDYZZEIBAPIN-VBQORRLJSA-N
Formula C15H18O9
HBA 9
HBD 6
MW 342.3
Rotatable Bonds 4
TPSA 156.91
LogP -1.55
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 342.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Moricandia arvensis Cruciferae-Brassicaceea Plantae 180540
2 Potamogeton perfoliatus Potamogetonaceae Plantae 55320

Showing of synonyms

  • Rezq S, Mahmoud M.F, et al. (2021). Anti-Inflammatory, Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study. Molecules, 2021, 26(16), 4826. [View] [PubMed]
  • Braham H, Mighri Z, et al. (2005). Antioxidant phenolic glycosides from Moricandia arvensis. Journal of Natural Products,2005,68(4),517-522. [View]
Pubchem: 5281761
Kegg Ligand: C10433
Chebi: 614
Nmrshiftdb2: 60026766
Metabolights: MTBLC614

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 342.3 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 342.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 342.3 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
56.46
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
11.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.19
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.46
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
-0.87
Rat (Acute)
1.91
Rat (Chronic Oral)
3.55
Fathead Minnow
4.09
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
501.69
Hydration Free Energy
-18.48
Log(D) at pH=7.4
-0.51
Log(P)
-1.06
Log S
-1.56
Log(Vapor Pressure)
-12.83
Melting Point
164.88
pKa Acid
5.44
pKa Basic
6.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9269
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9269
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9141
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9141
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9136
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9136
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9023
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9023
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8946
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8946
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8851
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8851
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8799
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8799
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8650
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8650
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8614
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8614
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8430
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8430
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8410
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8410
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8365
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8365
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8257
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8257
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8210
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8210
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8172
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8172
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8168
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8168
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7942
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7942
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7926
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7926
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7917
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7917
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7882
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7882
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7841
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7841
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7814
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7814
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7779
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7779
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7771
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7771
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7717
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7717
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7669
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7669
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7632
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7632
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7618
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7618
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7568
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7568
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7549
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7549
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7496
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7496
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7460
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7460
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7407
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7407
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7402
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7402
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7368
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7368
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7323
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7323
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7319
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7319
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7313
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7313
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7307
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7307
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7253
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7253
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7221
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7221
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7210
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7210
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7210
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7210
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7208
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7208
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7180
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7180
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7169
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7169
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7164
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7164
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7163
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7163
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7146
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7146
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7145
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7145
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7141
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7141
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7137
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7137
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7120
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7120
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7114
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7114
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7102
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7095
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7095
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7090
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7090
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7088
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7088
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7066
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7066
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7042
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7042
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7030
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7030
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7022
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7022
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7019
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7019
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7014
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7014
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7003
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7003
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7001
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7001

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