Levomefolate magnesiumProduct ingredient for Levomefolic acid

Name
Levomefolate magnesium
Drug Entry
Levomefolic acid

Levomefolic acid (INN) is the metabolite of folic acid (Vitamin B9) and it is a predominant active form of folate found in foods and in the blood circulation, accounting for 98% of folates in human plasma 8. It is transported across the membranes including the blood-brain barrier into various tissues where it plays an essential role in the DNA synthesis, cysteine cycle and regulation of homocysteine, where it methylates homocysteine and forms methionine and tetrahydrofolate (THF). Levomefolate is approved as a food additive and is designated a GRAS (generally regarded as safe) compound 13. It is available commercially as a crystalline form of the calcium salt (Metafolin(R)), which has the stability required for use as a supplement 8. Supplementation of levomefolic acid is desired over folic acid due to reduced potential for masking vitamin B12 deficiency symptoms.

Accession Number
DBSALT001534
Structure
Thumb
Synonyms
Not Available
UNII
1VZZ62R081
CAS Number
1429498-11-2
Weight
Average: 481.752
Monoisotopic: 481.15602319
Chemical Formula
C20H23MgN7O6
InChI Key
UNKHRTFYDNBUHK-QNTKWALQSA-L
InChI
InChI=1S/C20H25N7O6.Mg/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29;/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31);/q;+2/p-2/t12-,13-;/m0./s1
IUPAC Name
magnesium(2+) ion (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioate
SMILES
[Mg++].CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNC2=C1C(=O)N=C(N)N2
ChemSpider
32700282
Predicted Properties
PropertyValueSource
Water Solubility0.401 mg/mLALOGPS
logP1.4ALOGPS
logP-1.9ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)2.83ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area204.14 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity148.36 m3·mol-1ChemAxon
Polarizability45.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon