2-cyanocinnamic acid



Compound IDCDAMM00308
Common name2-cyanocinnamic acid
IUPAC name(E)-3-(2-cyanophenyl)prop-2-enoic acid
Molecular formulaC10H7NO2

Experimental data

Retention time11.619
Adduct[M+H]+
Actual mz174.055
Theoretical mz174.055
Error0.31
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.08

Identifiers and class information

Inchi keyHQVOPXGNHGTKOD-UHFFFAOYSA-N
SmilesN#CC=1C=CC=CC1C=CC(=O)O
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Plant source

  • Pedalium murex L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)4
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)173.171
    Computed dipole moment(dipole)6.726
    Total solvent accessible surface area (SASA)397.08
    Hydrophobic component of SASA (FOSA)16.441
    Hydrophilic component of SASA (FISA)180.866
    Pie component of the SASA (PISA)199.773
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)623.909
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)3.5
    Free energy of solvation of dipole (dip^2/V)0.0725189
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0088143
    Globularity descriptor (glob)0.889271
    Predicted polarizability in cubic angstroms (QPpolrz)18.154
    Predicted hexadecane/gas partition coefficient (QPlogPC16)6.837
    Predicted octanol/gas partition coefficient (QPlogPoct)10.144
    Predicted water/gas partition coefficient (QPlogPw)7.293
    Predicted octanol/water partition coefficient (QPlogPo/w)1.229
    Predicted aqueous solubility (QPlogS)-2.339
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.777
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.469
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)48.345
    Predicted brain/blood partition coefficient (QPlogBB)-1.202
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)23.808
    Predicted skin permeability, log Kp (QPlogKp)-3.765
    PM3 calculated ionization potential (IP(ev))9.997
    PM3 calculated electron affinity (EA(eV))1.37
    Number of likely metabolic reactions (#metab)0
    Prediction of binding to human serum albumin (QPlogKhsa)-0.64
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)64.286
    Solvent-accessible surface area of fluorine atoms (SAFluorine)0
    Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
    Van der Waals surface area (PSA)77.395
    Number of nitrogen and oxygen atoms (#NandO)3
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
    P23280CA6Carbonic anhydrase VIT06569SEA
    P27338MAOBMonoamine oxidase BT83011SEA
    P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SEA
    P03372ESR1Estrogen receptor alphaT02506SEA
    Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P43116PTGER2Prostanoid EP2 receptorT38529SEA
    P35408PTGER4Prostanoid EP4 receptorT18876SEA
    P43115PTGER3Prostanoid EP3 receptorT85467SEA
    Q03405PLAURUrokinase plasminogen activator surface receptorT74363SEA
    P02768ALBSerum albuminT63068SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
    T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
    T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
    T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
    T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
    T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
    T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
    T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
    T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
    T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
    T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
    T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
    T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
    T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
    T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
    T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
    T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
    T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
    T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
    T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
    T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
    T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
    T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
    T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
    T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
    T74363DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q03405PLAUR
    T74363DI0404Thrombocytosis[ICD-11: 3B63]Q03405PLAUR
    T63068DI0029Aneurysm/dissection[ICD-11: BD50]P02768ALB
    T63068DI0059Bowel habit change[ICD-11: ME05]P02768ALB
    T63068DI0077Cholelithiasis[ICD-11: DC11]P02768ALB
    T63068DI0202Inborn energy metabolism error[ICD-11: 5C53]P02768ALB
    T63068DI0218Irritable bowel syndrome[ICD-11: DD91]P02768ALB
    T63068DI0343Preprocedural examination[ICD-11: QA0B]P02768ALB
    T63068DI0366Rheumatoid arthritis[ICD-11: FA20]P02768ALB
    T63068DI0370Schizophrenia[ICD-11: 6A20]P02768ALB
    T63068DI0420Unspecific body region injury[ICD-11: ND56]P02768ALB

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