4,5-di-p-cis-coumaroylquinic acid



Compound IDCDAMM02030
Common name4,5-di-p-cis-coumaroylquinic acid
IUPAC name1,3-dihydroxy-4,5-bis[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexane-1-carboxylic acid
Molecular formulaC25H24O10

Experimental data

Retention time11.99
Adduct[M+K]+
Actual mz523.098
Theoretical mz523.1
Error4.7
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9146

Identifiers and class information

Inchi keyNRDKGYVJVVIBTH-BRKZRULUSA-N
SmilesO=C(OC1CC(O)(C(=O)O)CC(O)C1OC(=O)C=CC2=CC=C(O)C=C2)C=CC3=CC=C(O)C=C3
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)13
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)484.459
Computed dipole moment(dipole)8.591
Total solvent accessible surface area (SASA)800.313
Hydrophobic component of SASA (FOSA)129.768
Hydrophilic component of SASA (FISA)309.528
Pie component of the SASA (PISA)361.017
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1452.36
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)9.95
Free energy of solvation of dipole (dip^2/V)0.0508163
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0278002
Globularity descriptor (glob)0.774977
Predicted polarizability in cubic angstroms (QPpolrz)47.07
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.739
Predicted octanol/gas partition coefficient (QPlogPoct)29.653
Predicted water/gas partition coefficient (QPlogPw)20.462
Predicted octanol/water partition coefficient (QPlogPo/w)2.455
Predicted aqueous solubility (QPlogS)-4.828
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.533
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.087
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.912
Predicted brain/blood partition coefficient (QPlogBB)-3.656
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.143
Predicted skin permeability, log Kp (QPlogKp)-4.704
PM3 calculated ionization potential (IP(ev))9.005
PM3 calculated electron affinity (EA(eV))0.712
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.259
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)49.626
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)196.909
Number of nitrogen and oxygen atoms (#NandO)10
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
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
P15144ANPEPAminopeptidase NT67272SwissTargetPrediction
P09960LTA4HLeukotriene A4 hydrolaseT03691SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
Q9H3R0KDM4CLysine-specific demethylase 4CT73863SwissTargetPrediction
O75164KDM4ALysine-specific demethylase 4AT18904SwissTargetPrediction
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P45983MAPK8c-Jun N-terminal kinase 1T40097SwissTargetPrediction
P15090FABP4Fatty acid binding protein adipocyteT07217SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P10827THRAThyroid hormone receptor alphaT79591SwissTargetPrediction
P10828THRBThyroid hormone receptor beta-1T98933SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P13497BMP1Bone morphogenetic protein 1T53350SwissTargetPrediction
P42575CASP2Caspase-2T09128SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
Q99685MGLLMonoglyceride lipaseT18664SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
P16581SELESelectin ET72835SwissTargetPrediction
P29466CASP1Caspase-1T98269SwissTargetPrediction
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
Q9BYF1ACE2Angiotensin-converting enzyme 2T27889SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
Q9ULW8PADI3Protein-arginine deiminase type-3T36612SwissTargetPrediction
Q9UM07PADI4Protein-arginine deiminase type-4T50429SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
Q99558MAP3K14Mitogen-activated protein kinase kinase kinase 14T95736SwissTargetPrediction
P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P55210CASP7Caspase-7T72252SwissTargetPrediction
Q92793CREBBPCREB-binding protein/p53T03634SwissTargetPrediction
P10619CTSALysosomal protective proteinT37154SwissTargetPrediction
P16109SELPP-selectinT10965SwissTargetPrediction
P14151SELLLeukocyte adhesion molecule-1T60526SwissTargetPrediction
P55212CASP6Caspase-6T20600SwissTargetPrediction
Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SwissTargetPrediction
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
P28074PSMB5Proteasome Macropain subunit MB1T49031SwissTargetPrediction
P14679TYRTyrosinaseT97035SwissTargetPrediction
P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction
P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
P16885PLCG2Phospholipase C-gamma-2T93922SEA
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
O75173ADAMTS4ADAMTS4T79570SwissTargetPrediction
Q01064PDE1BPhosphodiesterase 1BT77613SwissTargetPrediction
O43826SLC37A4Glucose-6-phosphate translocaseT47306SwissTargetPrediction and SEA
Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
T67272DI0351Psoriasis[ICD-11: EA90]P15144ANPEP
T03691DI0012Acute myeloid leukaemia[ICD-11: 2A60]P09960LTA4H
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
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
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
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T31204DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P41595HTR2B
T31204DI0117Depression[ICD-11: 6A70-6A7Z]P41595HTR2B
T31204DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P41595HTR2B
T31204DI0354Psychotic disorder[ICD-11: 6A20-6A25]P41595HTR2B
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T40097DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45983MAPK8
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T79591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10827THRA
T79591DI0197Hypo-thyroidism[ICD-11: 5A00]P10827THRA
T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T72835DI0012Acute myeloid leukaemia[ICD-11: 2A60]P16581SELE
T72835DI0037Asthma[ICD-11: CA23]P16581SELE
T72835DI0039Atopic eczema[ICD-11: EA80]P16581SELE
T72835DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P16581SELE
T72835DI0088Circulatory system disease[ICD-11: BE2Z]P16581SELE
T72835DI0190Hypertension[ICD-11: BA00-BA04]P16581SELE
T72835DI0351Psoriasis[ICD-11: EA90]P16581SELE
T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T27889DI0009Acute diabete complication[ICD-11: 5A2Y]Q9BYF1ACE2
T27889DI0217Intrathoracic organs injury[ICD-11: NB32]Q9BYF1ACE2
T27889DI0356Pulmonary hypertension[ICD-11: BB01]Q9BYF1ACE2
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
T03634DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q92793CREBBP
T03634DI0346Prostate cancer[ICD-11: 2C82]Q92793CREBBP
T03634DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92793CREBBP
T03634DI0399Systemic sclerosis[ICD-11: 4A42]Q92793CREBBP
T37154DI0009Acute diabete complication[ICD-11: 5A2Y]P10619CTSA
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
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
T77613DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q01064PDE1B

Copyright © 2025