Sinapic acid - Compound Card

Sinapic acid

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Sinapic acid

Structure
Zoomed Structure
  • Family: Plantae - Amaranthaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Gallic Acid Derivative
Canonical Smiles COc1cc(/C=C/C(=O)O)cc(c1O)OC
InChI InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
InChIKey PCMORTLOPMLEFB-ONEGZZNKSA-N
Formula C11H12O5
HBA 4
HBD 2
MW 224.21
Rotatable Bonds 4
TPSA 75.99
LogP 1.51
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 224.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Limoniastrum guyonianum Plumbaginaceae Plantae 114145
2 Achyranthes aspera Amaranthaceae Plantae 240005

Showing of synonyms

  • Ndhlala AR, Ghebrehiwot HM, et al. (2015). Antimicrobial, anthelmintic activities and characterisation of functional phenolic acids of Achyranthes aspera linn.: a medicinal plant used for the treatment of wounds and Ringworm in East Africa.. Frontiers in pharmacology,2015,6,274. [View] [PubMed]
  • Trabelsi N, Oueslati S, et al. (2013). Phenolic contents and biological activities of Limoniastrum guyonianum fractions obtained by Centrifugal Partition Chromatography. Industrial Crops and Products,2013,49,740-746. [View]
Pubchem: 637775
Kegg Ligand: C00482
Chebi: 15714
Nmrshiftdb2: 20035521
Metabolights: MTBLC15714
Drugbank: DB08587
Pdb Ligand: SXX
Bindingdb: 50341142
CPRiL: 63027
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 224.21 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
24.46
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
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
10.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.630
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.040
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.530
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
3.200
Rat (Acute)
1.780
Rat (Chronic Oral)
2.680
Fathead Minnow
3.980
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
332.740
Hydration Free Energy
-11.350
Log(D) at pH=7.4
-0.970
Log(P)
1.28
Log S
-2.64
Log(Vapor Pressure)
-6.42
Melting Point
190.95
pKa Acid
5.04
pKa Basic
3.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9456
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9456
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9404
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9404
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.9373
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.9373
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9352
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9352
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9274
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9274
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9211
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9211
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 3 0.9171
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 3 0.9171
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9166
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9166
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9071
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9071
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8894
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8894
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8664
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8664
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8591
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8591
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8461
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8461
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 4 0.8439
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 4 0.8439
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.8353
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.8353
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8236
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8236
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8226
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8226
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8190
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8190
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 4 0.8174
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 4 0.8174
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.8075
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.8075
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8039
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8039
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.8021
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.8021
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 4 0.7924
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 4 0.7924
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7895
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7895
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7835
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7835
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7812
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7812
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7787
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7787
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7749
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7749
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7741
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7741
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7730
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7730
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.7684
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.7684
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7651
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7651
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7638
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7638
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7637
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7637
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7615
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7615
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7611
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7611
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7595
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7595
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7583
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7583
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7554
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7554
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7538
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7538
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7473
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7473
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 4 0.7468
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 4 0.7468
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7438
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7438
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7436
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7436
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7417
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7417
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7397
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7397
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7391
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7391
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7381
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7381
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7326
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7326
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7303
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7303
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7295
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7295
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7291
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7291
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7287
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7287
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7259
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7259
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7241
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7241
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7204
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7204
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7193
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7193
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7145
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7145
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7141
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7141
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7125
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7125
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7105
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7105
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7100
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7100
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7089
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7089
Serine/threonine-protein kinase RIO1 Q9BRS2 RIOK1_HUMAN Homo sapiens 3 0.7071
Serine/threonine-protein kinase RIO1 Q9BRS2 RIOK1_HUMAN Homo sapiens 3 0.7071
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7064
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7064
Bifunctional protein GAL10 P04397 GAL10_YEAST Saccharomyces cerevisiae 4 0.7051
Bifunctional protein GAL10 P04397 GAL10_YEAST Saccharomyces cerevisiae 4 0.7051
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7047
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7047
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7040
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7040
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7036
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7036

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