2-(4-carboxy-3-methoxystyryl)-2-methoxysuccinic acid - Compound Card

2-(4-carboxy-3-methoxystyryl)-2-methoxysuccinic acid

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2-(4-carboxy-3-methoxystyryl)-2-methoxysuccinic acid

Structure
Zoomed Structure
  • Family: Rosaceae
  • Kingdom: Plantae
  • Class: Monoaromatic
Canonical Smiles COc1cc(ccc1C(=O)O)/C=C/C(C(=O)O)(CC(=O)O)OC
InChI InChI=1S/C15H16O8/c1-22-11-7-9(3-4-10(11)13(18)19)5-6-15(23-2,14(20)21)8-12(16)17/h3-7H,8H2,1-2H3,(H,16,17)(H,18,19)(H,20,21)/b6-5+
InChIKey SMWPODZFOYKZAS-AATRIKPKSA-N
Formula C15H16O8
HBA 5
HBD 3
MW 324.29
Rotatable Bonds 8
TPSA 130.36
LogP 1.35
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 324.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sanguisorba minor Rosaceae Plantae 137456

Showing of synonyms

  • Ayoub NA (2003). Unique phenolic carboxylic acids from Sanguisorba minor. Phytochemistry,2003,63(4),433-436. [View] [PubMed]
Pubchem: 101251749

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.500
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.330
Plasma Protein Binding
30.13
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
-0.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.750
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
5.540
Rat (Acute)
2.050
Rat (Chronic Oral)
3.510
Fathead Minnow
4.050
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
359.570
Hydration Free Energy
-8.310
Log(D) at pH=7.4
-5.000
Log(P)
1.74
Log S
-2.68
Log(Vapor Pressure)
-10.1
Melting Point
170.41
pKa Acid
4.95
pKa Basic
5.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9454
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9454
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9431
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9431
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.9081
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.9081
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.8983
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.8983
Nitrogen regulatory protein P-II O66513 GLNB_AQUAE Aquifex aeolicus 3 0.8854
Nitrogen regulatory protein P-II O66513 GLNB_AQUAE Aquifex aeolicus 3 0.8854
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8702
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8702
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8583
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8583
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8571
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8571
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 3 0.8510
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 3 0.8510
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.8503
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.8503
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8480
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8480
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 3 0.8241
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 3 0.8241
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8172
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8172
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 3 0.8128
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 3 0.8128
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8077
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8077
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.8059
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.8059
D-3-phosphoglycerate dehydrogenase P9WNX3 SERA_MYCTU Mycobacterium tuberculosis 3 0.8028
D-3-phosphoglycerate dehydrogenase P9WNX3 SERA_MYCTU Mycobacterium tuberculosis 3 0.8028
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.7931
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.7931
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7923
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7923
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7866
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7866
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7864
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7864
Nitrogen regulatory protein P-II Q9L422 Q9L422_NOSS1 Nostoc sp 3 0.7837
Nitrogen regulatory protein P-II Q9L422 Q9L422_NOSS1 Nostoc sp 3 0.7837
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7812
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7812
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 4 0.7802
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 4 0.7802
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7786
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7786
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7736
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7736
MutT/nudix family protein O33199 O33199_MYCTO Mycobacterium tuberculosis 4 0.7710
MutT/nudix family protein O33199 O33199_MYCTO Mycobacterium tuberculosis 4 0.7710
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 3 0.7635
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 3 0.7635
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7599
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7599
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7596
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7596
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7593
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7593
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7531
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7531
Nucleoside diphosphate kinase, cytosolic P22887 NDKC_DICDI Dictyostelium discoideum 3 0.7511
Nucleoside diphosphate kinase, cytosolic P22887 NDKC_DICDI Dictyostelium discoideum 3 0.7511
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7502
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7502
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7497
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7497
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7472
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7472
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7445
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7445
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7437
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7437
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 3 0.7435
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 3 0.7435
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7412
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7412
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7397
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7397
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7394
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7394
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7377
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7377
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7360
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7360
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7352
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7352
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7332
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7332
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7296
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7296
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7288
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7288
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7287
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7287
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7287
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7287
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7258
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7258
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7254
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7254
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7239
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7239
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7219
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7219
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7217
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7217
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7215
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7215
Serine/threonine-protein kinase PLK Q4KMI8 Q4KMI8_DANRE Danio rerio 3 0.7201
Serine/threonine-protein kinase PLK Q4KMI8 Q4KMI8_DANRE Danio rerio 3 0.7201
DNA polymerase I, thermostable P19821 DPO1_THEAQ Thermus aquaticus 4 0.7190
DNA polymerase I, thermostable P19821 DPO1_THEAQ Thermus aquaticus 4 0.7190
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7177
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7177
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7173
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7173
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7171
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7171
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7162
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7162
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7159
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7159
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7145
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7145
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7140
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7140
Glycerol kinase P0A6F3 GLPK_ECOLI Escherichia coli 4 0.7132
Glycerol kinase P0A6F3 GLPK_ECOLI Escherichia coli 4 0.7132
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7126
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7126
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7121
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7121
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7116
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7116
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7111
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7111
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 3 0.7110
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 3 0.7110
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7105
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7105
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7101
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7101
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7082
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7082
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7081
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7081
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7073
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7073
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 2 0.7059
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 2 0.7059
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7058
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7058
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7050
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7050
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7042
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7042
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7041
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7041
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 3 0.7024
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 3 0.7024
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7016
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7016
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7000
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7000

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