Dihydrofolic acid



Compound IDCDAMM01776
Common nameDihydrofolic acid
IUPAC name2-[[4-[(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Molecular formulaC19H21N7O6

Experimental data

Retention time5.09
Adduct[M+H]+
Actual mz444.167
Theoretical mz444.162
Error10.19
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.9966

Identifiers and class information

Inchi keyOZRNSSUDZOLUSN-LBPRGKRZSA-N
SmilesO=C(O)CCC(NC(=O)C1=CC=C(C=C1)NCC2=NC=3C(=O)NC(=NC3NC2)N)C(=O)O
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)7
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)2
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)10
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)443.418
Computed dipole moment(dipole)13.989
Total solvent accessible surface area (SASA)751.215
Hydrophobic component of SASA (FOSA)124.863
Hydrophilic component of SASA (FISA)447.33
Pie component of the SASA (PISA)179.023
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1305.36
Number of hydrogen bond donors (donorHB)8.25
Number of hydrogen bond acceptors (accptHB)11.75
Free energy of solvation of dipole (dip^2/V)0.149911
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0449263
Globularity descriptor (glob)0.768932
Predicted polarizability in cubic angstroms (QPpolrz)41.375
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.797
Predicted octanol/gas partition coefficient (QPlogPoct)35.131
Predicted water/gas partition coefficient (QPlogPw)27.238
Predicted octanol/water partition coefficient (QPlogPo/w)-0.247
Predicted aqueous solubility (QPlogS)-3.85
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.101
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.51
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.036
Predicted brain/blood partition coefficient (QPlogBB)-5.083
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.013
Predicted skin permeability, log Kp (QPlogKp)-8.173
PM3 calculated ionization potential (IP(ev))7.001
PM3 calculated electron affinity (EA(eV))0.522
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-1.059
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)249.748
Number of nitrogen and oxygen atoms (#NandO)13
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction and SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P00491PNPPurine nucleoside phosphorylaseT78198SEA
O43174CYP26A1Cytochrome P450 26A1T84634SEA
Q9H244P2RY12Purinergic receptor P2Y12 (by homology)T46937SEA
Q9Y3Q0NAALAD2NAALADase IIT70036SEA
Q92820GGHGamma-glutamyl hydrolaseT71646SEA
P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction and SEA
Q13526PIN1Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1T16308SEA
P22102GARTGAR transformylaseT72042SwissTargetPrediction and SEA
Q99707MTRMethionine synthaseT21661SEA
P15328FOLR1Folate receptor alphaT83386SEA
P14207FOLR2Folate receptor betaT82297SEA
Q96NT5SLC46A1Proton-coupled folate transporterT19229SEA
P01275GCGGlucagonT44919SEA
Q04609FOLH1Glutamate carboxypeptidase IIT97071SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
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
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T46937DI0287Myocardial infarction[ICD-11: BA41-BA43]Q9H244P2RY12
T46937DI0405Thrombosis[ICD-11: DB61-GB90]Q9H244P2RY12
T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
T16308DI0238Lung cancer[ICD-11: 2C25]Q13526PIN1
T72042DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P22102GART
T83386DI0243Malaria[ICD-11: 1F40-1F45]P15328FOLR1
T83386DI0321Ovarian cancer[ICD-11: 2C73]P15328FOLR1
T19229DI0150Folate deficiency anaemia[ICD-11: 3A02]Q96NT5SLC46A1
T19229DI0231Leukaemia[ICD-11: 2A60-2B33]Q96NT5SLC46A1
T19229DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q96NT5SLC46A1
T44919DI0009Acute diabete complication[ICD-11: 5A2Y]P01275GCG
T44919DI0120Diabetes mellitus[ICD-11: 5A10]P01275GCG
T44919DI0308Obesity[ICD-11: 5B80-5B81]P01275GCG
T44919DI0331Parkinsonism[ICD-11: 8A00]P01275GCG
T44919DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P01275GCG
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1

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