Chlorogenic acid



Compound IDCDAMM00438
Common nameChlorogenic acid
IUPAC name3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Molecular formulaC16H18O9

Experimental data

Retention time14.35
Adduct[M+H]+
Actual mz355.099
Theoretical mz355.102
Error10.63
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.6592

Identifiers and class information

Inchi keyCWVRJTMFETXNAD-JUHZACGLSA-N
SmilesO=C(O)C1(O)CC(O)C(O)C(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1
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)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)354.313
Computed dipole moment(dipole)8.116
Total solvent accessible surface area (SASA)590.658
Hydrophobic component of SASA (FOSA)126.858
Hydrophilic component of SASA (FISA)315.584
Pie component of the SASA (PISA)148.216
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1042.16
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)9.65
Free energy of solvation of dipole (dip^2/V)0.0632101
Index of cohesive interaction in solids (ACxDN^.5/SA)0.040019
Globularity descriptor (glob)0.841624
Predicted polarizability in cubic angstroms (QPpolrz)30.548
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.52
Predicted octanol/gas partition coefficient (QPlogPoct)25.272
Predicted water/gas partition coefficient (QPlogPw)20.382
Predicted octanol/water partition coefficient (QPlogPo/w)-0.124
Predicted aqueous solubility (QPlogS)-2.32
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.853
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.994
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.552
Predicted brain/blood partition coefficient (QPlogBB)-3.009
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.991
Predicted skin permeability, log Kp (QPlogKp)-5.853
PM3 calculated ionization potential (IP(ev))9.1
PM3 calculated electron affinity (EA(eV))0.923
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.897
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)20.539
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)185.436
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction and SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q06124PTPN11Protein-tyrosine phosphatase 2CT13057SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
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
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
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
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
T13057DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06124PTPN11
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
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
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1

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