5,10-Methylene-6-Hydrofolic Acid

Identification

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Name
5,10-Methylene-6-Hydrofolic Acid
Accession Number
DB02301  (EXPT03070)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 455.424
Monoisotopic: 455.155331439
Chemical Formula
C20H21N7O6
InChI Key
BHJAPJNOACHPNI-CHWSQXEVSA-N
InChI
InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,7,12-13H,5-6,8-9H2,(H,23,30)(H,28,29)(H,32,33)(H3,21,24,25,31)/t12-,13-/m1/s1
IUPAC Name
(2R)-2-({4-[(6aS)-3-amino-1-oxo-1H,4H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
SMILES
NC1=NC(=O)C2=C(N1)N=C[C@@H]1CN(CN21)C1=CC=C(C=C1)C(=O)N[C@H](CCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
UFolylpolyglutamate synthaseNot AvailableLactobacillus casei
UThymidylate synthaseNot AvailableLactobacillus casei
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6323520
PubChem Substance
46505084
ChemSpider
4883459
HET
TMF
PDB Entries
1bjg / 1jbw / 1lce

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 Solubility0.335 mg/mLALOGPS
logP-0.78ALOGPS
logP-2.9ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)5.19ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area190.02 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity123.22 m3·mol-1ChemAxon
Polarizability44.33 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8396
Blood Brain Barrier+0.5847
Caco-2 permeable-0.8243
P-glycoprotein substrateSubstrate0.8286
P-glycoprotein inhibitor INon-inhibitor0.8892
P-glycoprotein inhibitor IINon-inhibitor0.9682
Renal organic cation transporterNon-inhibitor0.7227
CYP450 2C9 substrateNon-substrate0.8124
CYP450 2D6 substrateNon-substrate0.7915
CYP450 3A4 substrateSubstrate0.5078
CYP450 1A2 substrateNon-inhibitor0.7859
CYP450 2C9 inhibitorNon-inhibitor0.8954
CYP450 2D6 inhibitorNon-inhibitor0.8861
CYP450 2C19 inhibitorNon-inhibitor0.8759
CYP450 3A4 inhibitorNon-inhibitor0.838
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9791
Ames testNon AMES toxic0.6335
CarcinogenicityNon-carcinogens0.8988
BiodegradationNot ready biodegradable0.9708
Rat acute toxicity2.5384 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9343
hERG inhibition (predictor II)Non-inhibitor0.5339
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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
N-acyl-alpha amino acids / Hippuric acids / Pterins and derivatives / Phenylimidazolidines / Imidazopyrazines / Aniline and substituted anilines / Benzoyl derivatives / Dialkylarylamines / Pyrimidones / Aminopyrimidines and derivatives
show 14 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 / Phenylimidazolidine / Pteridine / Benzamide / Benzoic acid or derivatives
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 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
Lactobacillus casei
Pharmacological action
Unknown
General Function
Tetrahydrofolylpolyglutamate synthase activity
Specific Function
Conversion of folates to polyglutamate derivatives. It prefers 5,10-methylenetetrahydrofolate, rather than 10-formyltetrahydrofolate as folate substrate.
Gene Name
fgs
Uniprot ID
P15925
Uniprot Name
Folylpolyglutamate synthase
Molecular Weight
46588.815 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
Lactobacillus casei
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis.
Gene Name
thyA
Uniprot ID
P00469
Uniprot Name
Thymidylate synthase
Molecular Weight
36579.235 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]

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 17:18