3,4-Methylenedioxybenzoic acid



Compound IDCDAMM00797
Common name3,4-Methylenedioxybenzoic acid
IUPAC name1,3-benzodioxole-5-carboxylic acid
Molecular formulaC8H6O4

Experimental data

Retention time15.73
Adduct[M+H]+
Actual mz167.036
Theoretical mz167.034
Error7.93
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.3383

Identifiers and class information

Inchi keyVDVJGIYXDVPQLP-UHFFFAOYSA-N
SmilesO=C(O)C1=CC=C2OCOC2=C1
SuperclassOrganoheterocyclic compounds
ClassBenzodioxoles

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)1
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)166.133
Computed dipole moment(dipole)5.516
Total solvent accessible surface area (SASA)312.406
Hydrophobic component of SASA (FOSA)72.6
Hydrophilic component of SASA (FISA)105.626
Pie component of the SASA (PISA)134.18
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)497.14
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.0612009
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0112034
Globularity descriptor (glob)0.971474
Predicted polarizability in cubic angstroms (QPpolrz)14.381
Predicted hexadecane/gas partition coefficient (QPlogPC16)5.343
Predicted octanol/gas partition coefficient (QPlogPoct)8.435
Predicted water/gas partition coefficient (QPlogPw)6.794
Predicted octanol/water partition coefficient (QPlogPo/w)0.973
Predicted aqueous solubility (QPlogS)-0.86
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.763
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-0.826
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)249.949
Predicted brain/blood partition coefficient (QPlogBB)-0.243
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)140.584
Predicted skin permeability, log Kp (QPlogKp)-2.897
PM3 calculated ionization potential (IP(ev))9.462
PM3 calculated electron affinity (EA(eV))0.764
Number of likely metabolic reactions (#metab)0
Prediction of binding to human serum albumin (QPlogKhsa)-0.777
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)75.559
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)68.418
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)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P20309CHRM3Muscarinic acetylcholine receptor M3T67684SEA
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
P02766TTRTransthyretinT86462SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P31213SRD5A2Steroid 5-alpha-reductase 2T71390SwissTargetPrediction and SEA
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction and SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P27338MAOBMonoamine oxidase BT83011SEA
Q96RJ0TAAR1Trace amine-associated receptor 1 (by homology)T99524SEA
P05164MPOMyeloperoxidaseT23471SEA
Q99705MCHR1Melanin-concentrating hormone receptor 1T09572SEA
Q9H3R0KDM4CLysine-specific demethylase 4CT73863SEA
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
P14920DAOD-amino-acid oxidaseT33124SwissTargetPrediction
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
O75164KDM4ALysine-specific demethylase 4AT18904SEA
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
O15229KMOKynurenine 3-monooxygenaseT50973SEA
O00519FAAHAnandamide amidohydrolaseT11754SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
P08575PTPRCLeukocyte common antigenT43115SEA
P09467FBP1Fructose-1,6-bisphosphataseT83391SwissTargetPrediction
Q9Y4C1KDM3ALysine-specific demethylase 3AT25362SEA
Q9HC97GPR35G-protein coupled receptor 35T56143SEA
P21731TBXA2RThromboxane A2 receptorT76198SEA
P27695APEX1DNA-(apurinic or apyrimidinic site) lyaseT13348SwissTargetPrediction and SEA
P13497BMP1Bone morphogenetic protein 1T53350SEA
Q15722LTB4RLeukotriene B4 receptor 1T59626SEA
Q99685MGLLMonoglyceride lipaseT18664SEA
P10276RARARetinoic acid receptor alphaT94085SEA
O96017CHEK2Serine/threonine-protein kinase Chk2T28713SEA
P41229KDM5CLysine-specific demethylase 5CT85540SEA
P36897TGFBR1TGF-beta receptor type IT53389SEA
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SEA
P43115PTGER3Prostanoid EP3 receptorT85467SEA
Q9Y2K7KDM2ALysine-specific demethylase 2AT71949SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
O43174CYP26A1Cytochrome P450 26A1T84634SEA
P19793RXRARetinoid X receptor alpha (by homology)T13726SEA
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SEA
O76074PDE5APhosphodiesterase 5AT07663SEA
P53350PLK1Serine/threonine-protein kinase PLK1T40694SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
P01130LDLRLDL receptorT94692SEA
Q92630DYRK2Dual-specificity tyrosine-phosphorylation regulated kinase 2T39486SEA
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
P28702RXRBRetinoid X receptor betaT60077SEA
P13631RARGRetinoic acid receptor gammaT82146SEA
P48443RXRGRetinoid X receptor gammaT46456SEA
P10826RARBRetinoic acid receptor betaT61657SEA
P22736NR4A1Nuclear receptor subfamily 4 group A member 1T41119SEA
P41235HNF4AHepatocyte nuclear factor 4-alphaT15514SEA
P14618PKMPyruvate kinase isozymes M1/M2T65889SEA
O43353RIPK2Serine/threonine-protein kinase RIPK2T92463SEA
P04792HSPB1Heat shock protein beta-1T39921SEA
P36896ACVR1BActivin receptor type-1BT47594SEA
Q99527GPER1G-protein coupled estrogen receptor 1T65236SEA
Q13304GPR17Uracil nucleotide/cysteinyl leukotriene receptorT33902SwissTargetPrediction
Q9UPY5SLC7A11Cystine/glutamate transporterT11615SEA
P24557TBXAS1Thromboxane-A synthaseT78356SEA
P13674P4HA1Prolyl 4-hydroxylasesubunit alpha-1T61729SEA
P49019HCAR3Hydroxycarboxylic acid receptor 3T00890SEA
O43175PHGDHPhosphoglycerate dehydrogenaseT15139SEA
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
Q9UBS0RPS6KB2Ribosomal protein S6 kinase beta-2T42760SEA
P51843NR0B1Orphan nuclear receptor DAX-1T23191SEA
Q7RTX1TAS1R1Taste receptorT41263SEA
P43354NR4A2Orphan nuclear receptor NURR1T67163SEA
Q96LD8SENP8Deneddylase-1T13928SEA
Q9NPC1LTB4R2Leukotriene B4 receptor 2T30563SEA
Q16873LTC4SLeukotriene C4 synthaseT72881SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T67684DI0037Asthma[ICD-11: CA23]P20309CHRM3
T67684DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P20309CHRM3
T67684DI0154Functional bladder disorder[ICD-11: GC50]P20309CHRM3
T67684DI0166Glaucoma[ICD-11: 9C61]P20309CHRM3
T67684DI0293Nausea/vomiting[ICD-11: MD90]P20309CHRM3
T67684DI0333Peptic ulcer[ICD-11: DA61]P20309CHRM3
T67684DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P20309CHRM3
T67684DI0371Sebaceous gland disorder[ICD-11: ED91]P20309CHRM3
T67684DI0382Sjogren syndrome[ICD-11: 4A43]P20309CHRM3
T67684DI0411Tonus and reflex abnormality[ICD-11: MB47]P20309CHRM3
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
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
T71390DI0348Prostate hyperplasia[ICD-11: GA90]P31213SRD5A2
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
T99524DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q96RJ0TAAR1
T99524DI0149Focal/segmental autonomic disorder[ICD-11: 8D8A]Q96RJ0TAAR1
T99524DI0290Narcolepsy[ICD-11: 7A20]Q96RJ0TAAR1
T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
T09572DI0308Obesity[ICD-11: 5B80-5B81]Q99705MCHR1
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T33124DI0038Ataxic disorder[ICD-11: 8A03]P14920DAO
T33124DI0370Schizophrenia[ICD-11: 6A20]P14920DAO
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
T43115DI0012Acute myeloid leukaemia[ICD-11: 2A60]P08575PTPRC
T43115DI0414Transplanted organ/tissue[ICD-11: QB63]P08575PTPRC
T83391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P09467FBP1
T76198DI0102Coronary atherosclerosis[ICD-11: BA52]P21731TBXA2R
T76198DI0121Diabetic foot ulcer[ICD-11: BD54]P21731TBXA2R
T76198DI0287Myocardial infarction[ICD-11: BA41-BA43]P21731TBXA2R
T76198DI0378Sexual dysfunction[ICD-11: HA00-HA01]P21731TBXA2R
T13348DI0365Retinopathy[ICD-11: 9B71]P27695APEX1
T13348DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P27695APEX1
T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
T28713DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O96017CHEK2
T53389DI0035Arterial occlusive disease[ICD-11: BD40]P36897TGFBR1
T53389DI0238Lung cancer[ICD-11: 2C25]P36897TGFBR1
T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T40694DI0012Acute myeloid leukaemia[ICD-11: 2A60]P53350PLK1
T40694DI0284Myelodysplastic syndrome[ICD-11: 2A37]P53350PLK1
T40694DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P53350PLK1
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T94692DI0238Lung cancer[ICD-11: 2C25]P01130LDLR
T64205DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P42224STAT1
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T60077DI0225Kaposi sarcoma[ICD-11: 2B57]P28702RXRB
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
T46456DI0225Kaposi sarcoma[ICD-11: 2B57]P48443RXRG
T46456DI0232Light sensitivity impairment[ICD-11: 9D45]P48443RXRG
T61657DI0225Kaposi sarcoma[ICD-11: 2B57]P10826RARB
T65889DI0361Renal cell carcinoma[ICD-11: 2C90]P14618PKM
T92463DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]O43353RIPK2
T92463DI0339Postoperative inflammation[ICD-11: 1A00-CA43]O43353RIPK2
T39921DI0037Asthma[ICD-11: CA23]P04792HSPB1
T65236DI0100Contraceptive management[ICD-11: QA21]Q99527GPER1
T11615DI0054Body-focused behaviour disorder[ICD-11: 6B25]Q9UPY5SLC7A11
T78356DI0030Angina pectoris[ICD-11: BA40]P24557TBXAS1
T61729DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P13674P4HA1
T61729DI0413Transplant rejection[ICD-11: NE84]P13674P4HA1
T00890DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P49019HCAR3
T00890DI0128Dyslipidemia[ICD-11: 5C80-5C81]P49019HCAR3
T00890DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P49019HCAR3
T00890DI0351Psoriasis[ICD-11: EA90]P49019HCAR3
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T42760DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q9UBS0RPS6KB2
T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1
T30563DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q9NPC1LTB4R2
T30563DI0361Renal cell carcinoma[ICD-11: 2C90]Q9NPC1LTB4R2

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