Levomefolic acid

Details

• Internal ID: 69c4ac25-45f2-48b7-95ae-a51311371296
• Taxonomy: Organoheterocyclic compounds > Pteridines and derivatives > Pterins and derivatives > Tetrahydrofolic acids and derivatives > Tetrahydrofolic acids
• IUPAC Name: (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
• SMILES (Canonical): CN1C(CNC2=C1C(=O)NC(=N2)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
• SMILES (Isomeric): CN1[C@H](CNC2=C1C(=O)NC(=N2)N)CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
• InChI: InChI=1S/C20H25N7O6/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)/t12-,13-/m0/s1
• InChI Key: ZNOVTXRBGFNYRX-STQMWFEESA-N
• Popularity: 1,166 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅N₇O₆
• Molecular Weight: 459.50 g/mol
• Exact Mass: 459.18663154 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• 31690-09-2
• Levomefolinic acid
• LMSR
• L-methylfolate
• Nutrifolin
• L-5-MTHF
• Acido levomefolico
• 5-methyl-(6s)-tetrahydrofolic acid
• Acide levomefolique
• 8S95DH25XC
• (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
• DTXSID00185583
• L-methyl folate
• (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
• acidum levomefolicum
• (2S)-2-((4-(((6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid
• (2S)-2-((4-(((6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino)benzoyl)amino)pentanedioic acid
• L-methyltetrahydrofolate
• RefChem:799024
• DTXCID40108074
• 5-methyltetrahydrofolate, (L-Glu)-(S)-
• N-(4-((((6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamate
• 5-mthf
• Deplin
• LEVOMEFOLATE
• (S)-2-(4-((((S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
• Levomefolicacid
• 5-Methyltetrahydrofolate
• L-5-Methyltetrahydrofolate
• (6S)-5-methyltetrahydrofolate
• 5- methyltetrahydrofolate
• MFCD00870135
• [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate
• N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
• Metafolin (TN)
• (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• N-[4-({[(6S)-2-AMINO-4-HYDROXY-5-METHYL-5,6,7,8-TETRAHYDROPTERIDIN-6-YL]METHYL}AMINO)BENZOYL]-L-GLUTAMIC ACID
• N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid
• THH
• L-5-Methyltetrahydrofolic acid
• Levomefolic acid [USAN]
• Levomefolinic acid [USAN]
• UNII-8S95DH25XC
• (6s)-5-methyltetrahydrofolic acid
• (S)-2-[4-[[[(S)-2-Amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl]amino]benzamido]pentanedioic Acid
• N-(4-((((6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid
• N-[4-({[(6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
• LEVOMEFOLATE [VANDF]
• SCHEMBL79586
• Levomefolic acid (USAN/INN)
• Levomefolic acid [USAN:INN]
• L-METHYLFOLATE [VANDF]
• LEVOMEFOLIC ACID [INN]
• CHEMBL1231574
• SCHEMBL12704423
• SCHEMBL14462652
• SCHEMBL30051011
• SCHEMBL31090431
• (6S)-5-MTHF
• CHEBI:136009
• LEVOMEFOLIC ACID [WHO-DD]
• ZNOVTXRBGFNYRX-STQMWFEESA-N
• BDBM50391007
• EBC-27152
• MFCD21363683
• MSK000416
• s6909
• AKOS016008744
• AKOS025402272
• AC-7460
• AS-0793
• DB11256
• FL24884
• NCGC00378841-01
• NCGC00485934-01
• HY-14781
• L-Glutamic acid, N-(4-(((2-amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-, (S)-
• SY420414
• L0335
• NS00014759
• (6s)-5-methyl-5,6,7,8-tetrahydrofolic acid
• C00440
• D09353
• (6S)-5-METHYLTETRAHYDROFOLATE [WHO-DD]
• EN300-19768229
• Q192553
• BRD-K28580965-238-01-3
• BRD-K28580965-238-02-1
• Levomefolic acid 100 microg/mL in Acetonitrile:Water
• (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioicacid
• (2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• L-GLUTAMIC ACID, N-(4-((((6S)-2-AMINO-3,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6- PTERIDINYL)METHYL)AMINO)BENZOYL)-
• L-Glutamic acid, N-[4-[[(2-amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-
• N-(4-((((6S)-2-AMINO-5-METHYL-4-OXO-1,4,5,6,7,8-HEXAHYDROPTERIDIN-6- YL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID
• N-{[4-({[(6S)-2-amino-4-hydroxy-5-methyl-5,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid
• N-{[4-({[(6S)-2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6578	65.78%
Caco-2	-	0.8478	84.78%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Nucleus	0.5077	50.77%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9322	93.22%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9809	98.09%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9447	94.47%
P-glycoprotein inhibitior	-	0.7989	79.89%
P-glycoprotein substrate	+	0.7669	76.69%
CYP3A4 substrate	+	0.6046	60.46%
CYP2C9 substrate	-	0.7931	79.31%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.9463	94.63%
CYP2C9 inhibition	-	0.8537	85.37%
CYP2C19 inhibition	-	0.8801	88.01%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.8546	85.46%
CYP2C8 inhibition	-	0.8443	84.43%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9698	96.98%
Skin irritation	-	0.7768	77.68%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7905	79.05%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8685	86.85%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9502	95.02%
Acute Oral Toxicity (c)	III	0.5837	58.37%
Estrogen receptor binding	-	0.5639	56.39%
Androgen receptor binding	+	0.5888	58.88%
Thyroid receptor binding	+	0.6613	66.13%
Glucocorticoid receptor binding	-	0.5595	55.95%
Aromatase binding	+	0.5468	54.68%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9085	90.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6567	65.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.79%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	97.89%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	93.66%	93.10%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.27%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.93%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.71%	90.71%
CHEMBL202	P00374	Dihydrofolate reductase	91.29%	89.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.25%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	85.65%	97.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.89%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.62%	96.90%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.56%	100.00%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	83.27%	93.00%
CHEMBL1829	O15379	Histone deacetylase 3	82.94%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.99%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.80%	93.99%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.66%	95.83%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135398561
• LOTUS: LTS0136104
• wikiData: Q192553