(6R)-Folinic acid

Identification

Name
(6R)-Folinic acid
Accession Number
DB03256  (EXPT01470)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (6R,2'S)-Folinic acid
  • (6R)-Leucovorin
  • [6R]-5-formyl-5,6,7,8-tetrahydrofolate
  • L-Glutamic acid, N-[4-[[[(6R)-2-amino-5-formyl-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-
  • N-{[4-({[(6R)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid
External IDs
137643-04-0
Categories
Not Available
UNII
Not Available
CAS number
73951-54-9
Weight
Average: 473.4393
Monoisotopic: 473.165896125
Chemical Formula
C20H23N7O7
InChI Key
VVIAGPKUTFNRDU-OLZOCXBDSA-N
InChI
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13+/m1/s1
IUPAC Name
(2S)-2-{[4-({[(6R)-5-formyl-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
[H][[email protected]@](CCC(O)=O)(NC(=O)C1=CC=C(NC[[email protected]]2([H])CNC3=C(N2C=O)C(O)=NC(=N)N3)C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine hydroxymethyltransferaseNot AvailableGeobacillus kaustophilus (strain HTA426)
UAminomethyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UBifunctional polymyxin resistance protein ArnANot AvailableEscherichia coli (strain K12)
UFormimidoyltransferase-cyclodeaminaseNot AvailableHuman
UN,N-dimethylglycine oxidaseNot AvailableArthrobacter globiformis
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
PubChem Compound
135548
PubChem Substance
46506235
ChemSpider
119394
ChEMBL
CHEMBL1232801
HET
FON
PDB Entries
1kl2 / 1qd1 / 1vrq / 1xzq / 2bln / 3gee / 3geh / 4lxq / 4lxt / 4lxu
show 11 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 Solubility0.176 mg/mLALOGPS
logP-1.6ALOGPS
logP-4.2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)-3.2ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area216.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity137.48 m3·mol-1ChemAxon
Polarizability46.08 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5642
Blood Brain Barrier-0.7779
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7344
P-glycoprotein inhibitor INon-inhibitor0.918
P-glycoprotein inhibitor IINon-inhibitor0.984
Renal organic cation transporterNon-inhibitor0.8708
CYP450 2C9 substrateNon-substrate0.7887
CYP450 2D6 substrateNon-substrate0.814
CYP450 3A4 substrateNon-substrate0.5852
CYP450 1A2 substrateNon-inhibitor0.8748
CYP450 2C9 inhibitorNon-inhibitor0.9123
CYP450 2D6 inhibitorNon-inhibitor0.9326
CYP450 2C19 inhibitorNon-inhibitor0.8984
CYP450 3A4 inhibitorNon-inhibitor0.9475
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9292
Ames testNon AMES toxic0.7955
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable0.8534
Rat acute toxicity2.4254 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9283
hERG inhibition (predictor II)Non-inhibitor0.5331
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 / Aminobenzamides / Phenylalkylamines / Aniline and substituted anilines / Benzoyl derivatives / Secondary alkylarylamines / Hydroxypyrimidines / Dicarboxylic acids and derivatives
show 10 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 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Geobacillus kaustophilus (strain HTA426)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the reversible interconversion of serine and glycine with tetrahydrofolate (THF) serving as the one-carbon carrier. This reaction serves as the major source of one-carbon groups required ...
Gene Name
glyA
Uniprot ID
Q5KUI2
Uniprot Name
Serine hydroxymethyltransferase
Molecular Weight
45175.135 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
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name
gcvT
Uniprot ID
Q9WY54
Uniprot Name
Aminomethyltransferase
Molecular Weight
40332.235 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucuronate decarboxylase activity
Specific Function
Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-a...
Gene Name
arnA
Uniprot ID
P77398
Uniprot Name
Bifunctional polymyxin resistance protein ArnA
Molecular Weight
74288.175 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
Human
Pharmacological action
Unknown
General Function
Microtubule binding
Specific Function
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool.Binds and promotes bundling of vimentin...
Gene Name
FTCD
Uniprot ID
O95954
Uniprot Name
Formimidoyltransferase-cyclodeaminase
Molecular Weight
58925.93 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Catalyzes the oxidative demethylation of N,N-dimethylglycine to yield sarcosine, formaldehyde and hydrogen peroxide. The oxidation of dimethylglycine is coupled to the synthesis of 5,10-methylenete...
Gene Name
dmg
Uniprot ID
Q9AGP8
Uniprot Name
Dimethylglycine oxidase
Molecular Weight
89983.935 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:10