Trans-cinnamic acid - Compound Card

Trans-cinnamic acid

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Trans-cinnamic acid

Structure
Zoomed Structure
  • Family: Plantae - Amaranthaceae
  • Kingdom: Plantae, Animalia
  • Class: Monoaromatic
    • Subclass: Cinnamic Acid Derivative
Canonical Smiles OC(=O)/C=C/c1ccccc1
InChI InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChIKey WBYWAXJHAXSJNI-VOTSOKGWSA-N
Formula C9H8O2
HBA 1
HBD 1
MW 148.16
Rotatable Bonds 2
TPSA 37.3
LogP 1.78
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 148.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anastatica hierochuntica Cruciferae-Brassicaceea Plantae 663965
2 Apis mellifica Apidae Animalia 7460
3 Coriandrum sativum Apiaceae Plantae 4047
4 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]
  • Msaada K, Ben Jemia M, et al. (2014). Antioxidant activity of methanolic extracts from three coriander (Coriandrum sativum L.) fruit varieties. Arabian Journal of Chemistry,2014, in press. [View]
  • Boufadi YM, Soubhye J, et al. (2014). Characterization and antioxidant properties of six Algerian propolis extracts: ethyl acetate extracts inhibit myeloperoxidase activity. International Journal of Molecular Sciences,2014,15(2),2327-2345. [View] [PubMed]
  • Nakashima S, Matsuda H, et al. (2010). Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic and Medicinal Chemistry,2010,18(6),2337-2345. [View] [PubMed]
Pubchem: 444539
Kegg Ligand: C10438
Chebi: 35697
Nmrshiftdb2: 10113810
Metabolights: MTBLC35697
Drugbank: DB18313
Pdb Ligand: TCA
Bindingdb: 16430
CPRiL: 14536
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 148.16 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.77
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
48.5
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
4.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.1
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.36
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.34
Micronucleos
Safe
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
2.42
Rat (Acute)
1.84
Rat (Chronic Oral)
2.34
Fathead Minnow
3.96
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
287.63
Hydration Free Energy
-5.68
Log(D) at pH=7.4
-0.54
Log(P)
2.21
Log S
-2.85
Log(Vapor Pressure)
-3.19
Melting Point
172.9
pKa Acid
4.04
pKa Basic
-0.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.8031
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.8031
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7676
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7676
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7653
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7653
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7603
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7603
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7595
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7595
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7530
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7530
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7476
Major NAD(P)H-flavin oxidoreductase P46072 FRA1_ALIFS Aliivibrio fischeri 2 0.7476
Major NAD(P)H-flavin oxidoreductase P46072 FRA1_ALIFS Aliivibrio fischeri 2 0.7476
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7476
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7443
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7443
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7420
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7420
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7416
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7416
Tryptophan synthase beta chain 1 Q8U093 TRPB1_PYRFU Pyrococcus furiosus 3 0.7359
Tryptophan synthase beta chain 1 Q8U093 TRPB1_PYRFU Pyrococcus furiosus 3 0.7359
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7328
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7328
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7299
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7299
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7292
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7292
ATP-dependent helicase/nuclease subunit A P23478 ADDA_BACSU Bacillus subtilis 2 0.7280
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7280
ATP-dependent helicase/nuclease subunit A P23478 ADDA_BACSU Bacillus subtilis 2 0.7280
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7280
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7272
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7272
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7237
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7237
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7222
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7222
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 2 0.7215
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 2 0.7215
mRNA cleavage and polyadenylation factor CLP1 Q08685 CLP1_YEAST Saccharomyces cerevisiae 2 0.7201
mRNA cleavage and polyadenylation factor CLP1 Q08685 CLP1_YEAST Saccharomyces cerevisiae 2 0.7201
Acetylornithine/succinyldiaminopimelate aminotransferase P40732 ARGD_SALTY Salmonella typhimurium 2 0.7190
Acetylornithine/succinyldiaminopimelate aminotransferase P40732 ARGD_SALTY Salmonella typhimurium 2 0.7190
3-dehydroquinate dehydratase Q48255 AROQ_HELPY Helicobacter pylori 3 0.7181
3-dehydroquinate dehydratase Q48255 AROQ_HELPY Helicobacter pylori 3 0.7181
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 2 0.7175
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7175
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 2 0.7175
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7175
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7171
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7171
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7165
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7165
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7158
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7158
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7154
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7154
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7148
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7148
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7137
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7137
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7130
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7130
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7111
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7111
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7103
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7103
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 2 0.7097
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 2 0.7097
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7092
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7092
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 2 0.7087
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 2 0.7087
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7080
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7080
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7032
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7032
Uncharacterized ACR, COG1565 superfamily Q2T1U7 Q2T1U7_BURTA Burkholderia thailandensis 2 0.7031
Uncharacterized ACR, COG1565 superfamily Q2T1U7 Q2T1U7_BURTA Burkholderia thailandensis 2 0.7031
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7023
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7023
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7018
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7018
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7013
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7013
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7004
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7004

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