Dihydrofolic Acid

Identification

Name
Dihydrofolic Acid
Accession Number
DB02015  (EXPT01190)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-165989
Categories
Not Available
UNII
KXP0KNM559
CAS number
4033-27-6
Weight
Average: 443.4133
Monoisotopic: 443.155331439
Chemical Formula
C19H21N7O6
InChI Key
OZRNSSUDZOLUSN-LBPRGKRZSA-N
InChI
InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1
IUPAC Name
(2S)-2-[(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
SMILES
NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableEscherichia coli (strain K12)
UPutative pteridine reductase 2Not AvailableTrypanosoma cruzi
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001056
KEGG Compound
C00415
PubChem Compound
98792
PubChem Substance
46508318
ChemSpider
89228
BindingDB
18044
ChEBI
15633
ChEMBL
CHEMBL46294
HET
DHF
PDB Entries
1lcb / 1mxh / 1rf7 / 1tys / 2rk1 / 3dl5 / 3dl6 / 3frd / 4dpd / 4ez8
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.125 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.1ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)3.68ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area207.6 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.19 m3·mol-1ChemAxon
Polarizability44.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.705
Blood Brain Barrier-0.5071
Caco-2 permeable-0.8281
P-glycoprotein substrateSubstrate0.7761
P-glycoprotein inhibitor INon-inhibitor0.9644
P-glycoprotein inhibitor IINon-inhibitor0.9913
Renal organic cation transporterNon-inhibitor0.7889
CYP450 2C9 substrateNon-substrate0.7716
CYP450 2D6 substrateNon-substrate0.7893
CYP450 3A4 substrateNon-substrate0.6094
CYP450 1A2 substrateNon-inhibitor0.8946
CYP450 2C9 inhibitorNon-inhibitor0.9234
CYP450 2D6 inhibitorNon-inhibitor0.9149
CYP450 2C19 inhibitorNon-inhibitor0.9179
CYP450 3A4 inhibitorNon-inhibitor0.9163
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9818
Ames testNon AMES toxic0.7655
CarcinogenicityNon-carcinogens0.9417
BiodegradationNot ready biodegradable0.9719
Rat acute toxicity2.5993 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9649
hERG inhibition (predictor II)Non-inhibitor0.5959
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0322900000-3bd8be8b6fc531102b49
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0952200000-3a44b5c375b9b981244f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1930000000-71775fd6210c3e719dc1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0113900000-62b9c33c60c2e2fd46c6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xv-1349500000-3d3bae7b4497b96fc55d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9441000000-c0339a106358ca6d7221

Taxonomy

Description
This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Glutamic acid and derivatives
Alternative Parents
Hippuric acids / N-acyl-alpha amino acids / Pterins and derivatives / Aminobenzamides / Benzoyl derivatives / Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Hydroxypyrimidines / Dicarboxylic acids and derivatives
show 11 more
Substituents
Glutamic acid or derivatives / Hippuric acid or derivatives / Hippuric acid / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Pterin / Aminobenzamide / Aminobenzoic acid or derivatives / Pteridine / Benzamide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dihydrofolic acids (CHEBI:15633)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
folA
Uniprot ID
P0ABQ4
Uniprot Name
Dihydrofolate reductase
Molecular Weight
17999.21 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Not Available
Gene Name
ptr2
Uniprot ID
Q8I814
Uniprot Name
Putative pteridine reductase 2
Molecular Weight
29204.015 Da

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:10