(2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid



Compound IDCDAMM01039
Common name(2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid
IUPAC name3-(2,4-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
Score6.8343

Identifiers and class information

Inchi keyHGEFWFBFQKWVMY-DUXPYHPUSA-N
SmilesO=C(O)C=CC1=CC=C(O)C=C1O
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)9.154
Total solvent accessible surface area (SASA)386.785
Hydrophobic component of SASA (FOSA)19.497
Hydrophilic component of SASA (FISA)215.091
Pie component of the SASA (PISA)152.197
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)606.29
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.138223
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0156733
Globularity descriptor (glob)0.895672
Predicted polarizability in cubic angstroms (QPpolrz)16.353
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.064
Predicted octanol/gas partition coefficient (QPlogPoct)13.395
Predicted water/gas partition coefficient (QPlogPw)9.887
Predicted octanol/water partition coefficient (QPlogPo/w)0.547
Predicted aqueous solubility (QPlogS)-1.262
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.843
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.138
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)22.898
Predicted brain/blood partition coefficient (QPlogBB)-1.525
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)10.615
Predicted skin permeability, log Kp (QPlogKp)-4.467
PM3 calculated ionization potential (IP(ev))9.117
PM3 calculated electron affinity (EA(eV))0.753
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)-0.806
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)54.485
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)95.043
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
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SEA
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
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
P80404ABATGamma-amino-N-butyrate transaminaseT59045SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction and SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q9HC97GPR35G-protein coupled receptor 35T56143SEA
P11474ESRRAEstrogen-related receptor alphaT72841SEA
O95718ESRRBEstrogen-related receptor betaT42025SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P49759CLK1Dual specificty protein kinase CLK1T46685SEA
Q9Y463DYRK1BDual specificity tyrosine-phosphorylation-regulated kinase 1BT82720SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P43115PTGER3Prostanoid EP3 receptorT85467SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
O60344ECE2Endothelin-converting enzyme 2T16799SEA
P08236GUSBBeta-glucuronidaseT96413SEA
P14679TYRTyrosinaseT97035SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q9HBW0LPAR2Lysophosphatidic acid receptor Edg-4T39380SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q15120PDK3Pyruvate dehydrogenase kinase isoform 3T99029SEA
Q9UBY5LPAR3Lysophosphatidic acid receptor Edg-7T95923SEA
Q15466NR0B2Nuclear receptor subfamily 0 group B member 2T89859SEA
P51649ALDH5A1Succinate semialdehyde dehydrogenaseT13259SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
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
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
T59045DI0060Brain cancer[ICD-11: 2A00]P80404ABAT
T59045DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P80404ABAT
T59045DI0135Epileptic encephalopathy[ICD-11: 8A62]P80404ABAT
T59045DI0266Mineral deficiency[ICD-11: 5B5K]P80404ABAT
T59045DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P80404ABAT
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
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
T72841DI0366Rheumatoid arthritis[ICD-11: FA20]P11474ESRRA
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
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
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T96413DI0242Lysosomal disease[ICD-11: 5C56]P08236GUSB
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T95923DI0146Fibrosis[ICD-11: GA14-GC01]Q9UBY5LPAR3
T95923DI0399Systemic sclerosis[ICD-11: 4A42]Q9UBY5LPAR3
T13259DI0122Diagnostic imaging[ICD-11: N.A.]P51649ALDH5A1
T13259DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P51649ALDH5A1

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