3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid



Compound IDCDAMM00813
Common name3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
IUPAC name3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Molecular formulaC10H10O5

Experimental data

Retention time14.7
Adduct[M+H]+
Actual mz211.061
Theoretical mz211.06
Error3.43
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.6328

Identifiers and class information

Inchi keyYFXWTVLDSKSYLW-NSCUHMNNSA-N
SmilesO=C(O)C=CC1=CC(O)=C(O)C(OC)=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)6
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)210.186
Computed dipole moment(dipole)3.27
Total solvent accessible surface area (SASA)429.152
Hydrophobic component of SASA (FOSA)116.31
Hydrophilic component of SASA (FISA)215.536
Pie component of the SASA (PISA)97.306
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)688.917
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)4.25
Free energy of solvation of dipole (dip^2/V)0.0155202
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0171529
Globularity descriptor (glob)0.87902
Predicted polarizability in cubic angstroms (QPpolrz)18.493
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.422
Predicted octanol/gas partition coefficient (QPlogPoct)12.714
Predicted water/gas partition coefficient (QPlogPw)10.136
Predicted octanol/water partition coefficient (QPlogPo/w)0.719
Predicted aqueous solubility (QPlogS)-1.657
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.166
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.146
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)22.676
Predicted brain/blood partition coefficient (QPlogBB)-1.658
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)10.504
Predicted skin permeability, log Kp (QPlogKp)-4.573
PM3 calculated ionization potential (IP(ev))8.962
PM3 calculated electron affinity (EA(eV))0.924
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.745
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)55.417
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)102.986
Number of nitrogen and oxygen atoms (#NandO)5
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 and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction and SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SEA
P15121AKR1B1Aldose reductaseT26623SEA
P05164MPOMyeloperoxidaseT23471SEA
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
O14684PTGESProstaglandin E synthaseT02562SEA
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P05121SERPINE1Plasminogen activator inhibitor-1T15556SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
Q06124PTPN11Protein-tyrosine phosphatase 2CT13057SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P43115PTGER3Prostanoid EP3 receptorT85467SEA
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P41586ADCYAP1R1Pituitary adenylate cyclase-activating polypeptide type I receptorT92185SEA
Q15466NR0B2Nuclear receptor subfamily 0 group B member 2T89859SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9NR20DYRK4Dual-specificity tyrosine-phosphorylation regulated kinase 4T20542SEA

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
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
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
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
T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
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
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
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
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
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
T76914DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P22001KCNA3
T76914DI0351Psoriasis[ICD-11: EA90]P22001KCNA3
T76914DI0352Psoriatic arthritis[ICD-11: FA21]P22001KCNA3
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
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T92185DI0264Migraine[ICD-11: 8A80]P41586ADCYAP1R1

Copyright © 2025