Dicaffeoylquinic acid



Compound IDCDAMM01149
Common nameDicaffeoylquinic acid
IUPAC name3,5-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
Molecular formulaC25H24O12

Experimental data

Retention time0.25
Adduct[2M+Na]+
Actual mz1055.23
Theoretical mz1055.24
Error14.42
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8946

Identifiers and class information

Inchi keyKRZBCHWVBQOTNZ-PSEXTPKNSA-N
SmilesO=C(OC1CC(O)(C(=O)O)CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1O)C=CC3=CC=C(O)C(O)=C3
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)5
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)15
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)516.457
Computed dipole moment(dipole)4.097
Total solvent accessible surface area (SASA)822.45
Hydrophobic component of SASA (FOSA)129.968
Hydrophilic component of SASA (FISA)410.209
Pie component of the SASA (PISA)282.273
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1485.31
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)11.45
Free energy of solvation of dipole (dip^2/V)0.0113012
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0368337
Globularity descriptor (glob)0.765481
Predicted polarizability in cubic angstroms (QPpolrz)46.352
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.719
Predicted octanol/gas partition coefficient (QPlogPoct)32.844
Predicted water/gas partition coefficient (QPlogPw)24.63
Predicted octanol/water partition coefficient (QPlogPo/w)0.951
Predicted aqueous solubility (QPlogS)-4.236
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.417
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.865
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.323
Predicted brain/blood partition coefficient (QPlogBB)-5.008
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.106
Predicted skin permeability, log Kp (QPlogKp)-6.645
PM3 calculated ionization potential (IP(ev))8.753
PM3 calculated electron affinity (EA(eV))0.776
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.627
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)239.414
Number of nitrogen and oxygen atoms (#NandO)12
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction and SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction and SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
Q06124PTPN11Protein-tyrosine phosphatase 2CT13057SEA
P10276RARARetinoic acid receptor alphaT94085SEA
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P67775PPP2CASerine/threonine protein phosphatase 2A, catalytic subunit, alpha isoformT40491SwissTargetPrediction
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P13631RARGRetinoic acid receptor gammaT82146SEA
P10826RARBRetinoic acid receptor betaT61657SEA
Q01064PDE1BPhosphodiesterase 1BT77613SwissTargetPrediction
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SwissTargetPrediction and SEA
Q15466NR0B2Nuclear receptor subfamily 0 group B member 2T89859SEA
P10809HSPD1Mitochondrial matrix protein P1T11283SEA

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
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
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
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T13057DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06124PTPN11
T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T40491DI0268Molluscum contagiosum[ICD-11: 1E76]P67775PPP2CA
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
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
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T82146DI0005Acne vulgaris[ICD-11: ED80]P13631RARG
T82146DI0012Acute myeloid leukaemia[ICD-11: 2A60]P13631RARG
T82146DI0225Kaposi sarcoma[ICD-11: 2B57]P13631RARG
T82146DI0277Muscle calcification/ossification[ICD-11: FB31]P13631RARG
T82146DI0351Psoriasis[ICD-11: EA90]P13631RARG
T61657DI0225Kaposi sarcoma[ICD-11: 2B57]P10826RARB
T77613DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q01064PDE1B
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1

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