Dopaxanthin



Compound IDCDAMM01778
Common nameDopaxanthin
IUPAC name4-[2-[1-carboxy-2-(3,4-dihydroxyphenyl)ethyl]iminoethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid
Molecular formulaC18H18N2O8

Experimental data

Retention time9.57
Adduct[M+H]+
Actual mz391.108
Theoretical mz391.113
Error14.77
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.3174

Identifiers and class information

Inchi keyYSNPSKZBOQYUHH-AFUNOPLTSA-N
SmilesO=C(O)C1=CC(=CC=NC(C(=O)O)CC2=CC=C(O)C(O)=C2)CC(N1)C(=O)O
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)2
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)3
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)11
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)390.349
Computed dipole moment(dipole)13.109
Total solvent accessible surface area (SASA)567.9
Hydrophobic component of SASA (FOSA)125.035
Hydrophilic component of SASA (FISA)329.458
Pie component of the SASA (PISA)113.407
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1082.22
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)10
Free energy of solvation of dipole (dip^2/V)0.158794
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0431324
Globularity descriptor (glob)0.897644
Predicted polarizability in cubic angstroms (QPpolrz)31.176
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.919
Predicted octanol/gas partition coefficient (QPlogPoct)27.17
Predicted water/gas partition coefficient (QPlogPw)20.309
Predicted octanol/water partition coefficient (QPlogPo/w)0.999
Predicted aqueous solubility (QPlogS)-1.854
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.617
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)1.693
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.121
Predicted brain/blood partition coefficient (QPlogBB)-2.825
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.059
Predicted skin permeability, log Kp (QPlogKp)-6.136
PM3 calculated ionization potential (IP(ev))8.693
PM3 calculated electron affinity (EA(eV))1.116
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-1.104
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)3.414
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)214.553
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
Q14416GRM2Metabotropic glutamate receptor 2T62820SwissTargetPrediction
P07101THTyrosine 3-hydroxylaseT62390SEA
Q07075ENPEPAminopeptidase AT31956SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P08069IGF1RInsulin-like growth factor I receptorT48069SwissTargetPrediction
Q9HAN5TRP1Cationic trypsinogenT27602SwissTargetPrediction
P35916FLT4Vascular endothelial growth factor receptor 3T07303SwissTargetPrediction
Q02763TEKTyrosine-protein kinase TIE-2T92144SwissTargetPrediction
Q04760GLO1Glyoxalase IT88285SwissTargetPrediction
P98073TMPRSS15EnteropeptidaseT75772SwissTargetPrediction
P24593IGFBP5Insulin-like growth factor binding protein 5T17008SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
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
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T62820DI0025Alzheimer disease[ICD-11: 8A20]Q14416GRM2
T62820DI0051Bipolar disorder[ICD-11: 6A60]Q14416GRM2
T62820DI0116Dengue fever[ICD-11: 1D2Z]Q14416GRM2
T62820DI0117Depression[ICD-11: 6A70-6A7Z]Q14416GRM2
T62820DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]Q14416GRM2
T62820DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]Q14416GRM2
T62820DI0308Obesity[ICD-11: 5B80-5B81]Q14416GRM2
T62820DI0354Psychotic disorder[ICD-11: 6A20-6A25]Q14416GRM2
T62820DI0370Schizophrenia[ICD-11: 6A20]Q14416GRM2
T62390DI0019Adrenomedullary hyperfunction[ICD-11: 5A75]P07101TH
T62390DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P07101TH
T31956DI0190Hypertension[ICD-11: BA00-BA04]Q07075ENPEP
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T48069DI0276Multiple structural anomalies syndrome[ICD-11: LD2F]P08069IGF1R
T48069DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P08069IGF1R
T48069DI0408Thyrotoxicosis[ICD-11: 5A02]P08069IGF1R
T27602DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9HAN5TRP1
T27602DI0274Multiple myeloma[ICD-11: 2A83]Q9HAN5TRP1
T07303DI0361Renal cell carcinoma[ICD-11: 2C90]P35916FLT4
T92144DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q02763TEK
T92144DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]Q02763TEK
T92144DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q02763TEK
T92144DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q02763TEK
T92144DI0365Retinopathy[ICD-11: 9B71]Q02763TEK
T92144DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q02763TEK
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1

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