4-O-Cinnamoylquinic acid



Compound IDCDAMM00954
Common name4-O-Cinnamoylquinic acid
IUPAC name1,3,5-trihydroxy-4-(3-phenylprop-2-enoyloxy)cyclohexane-1-carboxylic acid
Molecular formulaC16H18O7

Experimental data

Retention time0.45
Adduct[M+Na]+
Actual mz345.093
Theoretical mz345.094
Error2.95
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.3082

Identifiers and class information

Inchi keyCLDAKARZYFIUGC-VOTSOKGWNA-N
SmilesO=C(OC1C(O)CC(O)(C(=O)O)CC1O)C=CC=2C=CC=CC2
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)322.314
Computed dipole moment(dipole)4.685
Total solvent accessible surface area (SASA)576.499
Hydrophobic component of SASA (FOSA)120.876
Hydrophilic component of SASA (FISA)232.339
Pie component of the SASA (PISA)223.284
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1005.97
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)8.15
Free energy of solvation of dipole (dip^2/V)0.0218207
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0282741
Globularity descriptor (glob)0.842213
Predicted polarizability in cubic angstroms (QPpolrz)31.1
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.66
Predicted octanol/gas partition coefficient (QPlogPoct)20.947
Predicted water/gas partition coefficient (QPlogPw)16.327
Predicted octanol/water partition coefficient (QPlogPo/w)1.113
Predicted aqueous solubility (QPlogS)-2.792
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.885
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.342
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)15.712
Predicted brain/blood partition coefficient (QPlogBB)-2.102
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.065
Predicted skin permeability, log Kp (QPlogKp)-4.247
PM3 calculated ionization potential (IP(ev))9.421
PM3 calculated electron affinity (EA(eV))0.732
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.655
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)54.871
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)142.622
Number of nitrogen and oxygen atoms (#NandO)7
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P23280CA6Carbonic anhydrase VIT06569SEA
P27338MAOBMonoamine oxidase BT83011SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P45983MAPK8c-Jun N-terminal kinase 1T40097SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction and SEA
P09467FBP1Fructose-1,6-bisphosphataseT83391SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SEA
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction
Q99685MGLLMonoglyceride lipaseT18664SwissTargetPrediction
O15111CHUKInhibitor of NF-kappa-B kinase (IKK)T78429SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9Y3Q0NAALAD2NAALADase IIT70036SwissTargetPrediction
P13569CFTRCystic fibrosis transmembrane conductance regulatorT55654SwissTargetPrediction
P53396ACLYATP-citrate synthaseT52189SwissTargetPrediction
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
O75884RBBP9Putative hydrolase RBBP9T12084SEA
Q01064PDE1BPhosphodiesterase 1BT77613SwissTargetPrediction
O43826SLC37A4Glucose-6-phosphate translocaseT47306SwissTargetPrediction and SEA
Q9P0U3SENP1Sentrin-specific protease 1T96435SEA
P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
P55011SLC12A2Na-K-Cl cotransporterT85581SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T40097DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45983MAPK8
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T83391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P09467FBP1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
T78429DI0250Mature B-cell lymphoma[ICD-11: 2A85]O15111CHUK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T55654DI0110Cystic fibrosis[ICD-11: CA25]P13569CFTR
T55654DI0217Intrathoracic organs injury[ICD-11: NB32]P13569CFTR
T55654DI0435Viral intestinal infection[ICD-11: 1A2Z]P13569CFTR
T52189DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P53396ACLY
T17852DI0025Alzheimer disease[ICD-11: 8A20]O76083PDE9A
T17852DI0115Dementia[ICD-11: 6D80-6D8Z]O76083PDE9A
T17852DI0165Genitourinary disease[ICD-11: GA0Z-GC8Z]O76083PDE9A
T17852DI0175Heart failure[ICD-11: BD10-BD1Z]O76083PDE9A
T17852DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O76083PDE9A
T17852DI0331Parkinsonism[ICD-11: 8A00]O76083PDE9A
T17852DI0370Schizophrenia[ICD-11: 6A20]O76083PDE9A
T17852DI0381Sickle-cell disorder[ICD-11: 3A51]O76083PDE9A
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T77613DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q01064PDE1B
T85581DI0175Heart failure[ICD-11: BD10-BD1Z]P55011SLC12A2

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