Caffeic acid



Compound IDCDAMM00785
Common nameCaffeic acid
IUPAC name3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Molecular formulaC9H8O4

Experimental data

Retention time0.28
Adduct[2M+Na]+
Actual mz383.071
Theoretical mz383.073
Error5.53
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1265

Identifiers and class information

Inchi keyQAIPRVGONGVQAS-RQOWECAXSA-N
SmilesO=C(O)C=CC1=CC=C(O)C(O)=C1
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

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)5
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)180.16
Computed dipole moment(dipole)6.439
Total solvent accessible surface area (SASA)390.034
Hydrophobic component of SASA (FOSA)23.691
Hydrophilic component of SASA (FISA)216.706
Pie component of the SASA (PISA)149.637
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)609.812
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.0679829
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0155427
Globularity descriptor (glob)0.891648
Predicted polarizability in cubic angstroms (QPpolrz)16.469
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.059
Predicted octanol/gas partition coefficient (QPlogPoct)12.468
Predicted water/gas partition coefficient (QPlogPw)9.888
Predicted octanol/water partition coefficient (QPlogPo/w)0.55
Predicted aqueous solubility (QPlogS)-1.311
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.843
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.191
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)22.104
Predicted brain/blood partition coefficient (QPlogBB)-1.555
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)10.218
Predicted skin permeability, log Kp (QPlogKp)-4.506
PM3 calculated ionization potential (IP(ev))9.043
PM3 calculated electron affinity (EA(eV))0.912
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)-0.802
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)54.229
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)95.859
Number of nitrogen and oxygen atoms (#NandO)4
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
P00533EGFREpidermal growth factor receptor erbB1T59328SEA
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SEA
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SEA
P21397MAOAMonoamine oxidase AT83875SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction and SEA
P16083NQO2Quinone reductase 2T75498SEA
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction and SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
P27338MAOBMonoamine oxidase BT83011SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction and SEA
P07101THTyrosine 3-hydroxylaseT62390SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction and SEA
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction and SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction and SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
Q06124PTPN11Protein-tyrosine phosphatase 2CT13057SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P10276RARARetinoic acid receptor alphaT94085SEA
P05186ALPLAlkaline phosphatase, tissue-nonspecific isozymeT09538SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
P08263GSTA1Glutathione S-transferase A1T17221SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P43115PTGER3Prostanoid EP3 receptorT85467SEA
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P10696ALPGAlkaline phosphatase placental-likeT35565SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
P37840SNCAAlpha-synucleinT03644SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P13631RARGRetinoic acid receptor gammaT82146SEA
P10826RARBRetinoic acid receptor betaT61657SEA
Q02779MAP3K10Mitogen-activated protein kinase kinase kinase 10T89323SEA
Q96RR4CAMKK2CaM-kinase kinase betaT82262SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
P24593IGFBP5Insulin-like growth factor binding protein 5T17008SEA
P24592IGFBP6Insulin-like growth factor binding protein 6T61800SEA
P18065IGFBP2Insulin-like growth factor binding protein 2T64268SEA
P08833IGFBP1Insulin-like growth factor binding protein 1T15048SEA
Q15466NR0B2Nuclear receptor subfamily 0 group B member 2T89859SEA
P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
P28476GABRR2GABA(A) receptor rho2T90682SEA
P10809HSPD1Mitochondrial matrix protein P1T11283SEA
P01100FOSProto-oncogene c-FosT28025SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T34429DI0101Corneal disease[ICD-11: 9A76-9A78]P36544CHRNA7
T34429DI0370Schizophrenia[ICD-11: 6A20]P36544CHRNA7
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
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
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
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
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
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
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T62390DI0019Adrenomedullary hyperfunction[ICD-11: 5A75]P07101TH
T62390DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P07101TH
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
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
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
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
T13057DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06124PTPN11
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
T09538DI0164Genetic prion disease[ICD-11: 8E02]P05186ALPL
T09538DI0330Parasitic infection[ICD-11: 1D0Y-1G2Z]P05186ALPL
T11451DI0095Colorectal cancer[ICD-11: 2B91]Q9NR96TLR9
T11451DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q9NR96TLR9
T11451DI0252Melanoma[ICD-11: 2C30]Q9NR96TLR9
T11451DI0346Prostate cancer[ICD-11: 2C82]Q9NR96TLR9
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
T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
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
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T03644DI0025Alzheimer disease[ICD-11: 8A20]P37840SNCA
T03644DI0044Autonomic nervous system disorder[ICD-11: 8D87]P37840SNCA
T03644DI0331Parkinsonism[ICD-11: 8A00]P37840SNCA
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
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1

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