Ng-monomethyl-l-arginine

Details

• Internal ID: 8b437aa2-f714-4bb5-969d-7d6a083fb750
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Arginine and derivatives
• IUPAC Name: (2S)-2-amino-5-[(N'-methylcarbamimidoyl)amino]pentanoic acid
• InChI: InChI=1S/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11)/t5-/m0/s1
• InChI Key: NTNWOCRCBQPEKQ-YFKPBYRVSA-N
• Popularity: 5,315 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₆N₄O₂
• Molecular Weight: 188.23 g/mol
• Exact Mass: 188.12732577 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -1.29
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• L-NMMA
• 17035-90-4
• NG-Monomethyl-L-arginine
• N-Methylarginine
• NG-Methylarginine
• tilarginina
• omega-N-Monomethylarginine
• N(G)-Methylarginine
• L-NG-Monomethyl Arginine
• tilargininum
• N5-(Methylamidino)-L-ornithine
• (2S)-2-amino-5-[(N'-methylcarbamimidoyl)amino]pentanoic acid
• 27JT06E6GR
• (2S)-2-amino-5-((N'-methylcarbamimidoyl)amino)pentanoic acid
• RefChem:1092346
• (2S)-2-azaniumyl-5-((N'-methylcarbamimidoyl)amino)pentanoate
• Targinine
• L-Monomethylarginine
• N-Monomethyl-L-arginine
• omega-N-METHYLARGININE
• N(G)-Monomethyl-L-arginine
• Nomega-Monomethyl-L-arginine Acetate
• Tilarginine [INN]
• Ngamma-Monomethyl-L-arginine
• L-Targinine
• N(omega)-methyl-L-arginine
• N-omega-monomethyl-L-arginine
• (S)-2-Amino-5-(3-methylguanidino)pentanoic acid
• NG-Monomethyl-L-arginine acetate
• Nw-methyl-L-arginine
• N(5)-(methylamidino)-L-ornithine
• .omega.-n-methylarginine
• N(5)-(N-methylcarbamimidoyl)-L-ornithine
• (2S)-2-amino-5-(N'-methylcarbamimidamido)pentanoic acid
• CHEMBL256147
• N(5)-[imino(methylamino)methyl]-L-ornithine
• L-Arginine, 2
• (2S)-2-amino-5-[(N-methylcarbamimidoyl)amino]pentanoic acid
• N~5~-(N-methylcarbamimidoyl)-L-ornithine
• H-Arg(me)-OH
• Arginine, L-NG-Monomethyl
• targinina
• targininum
• CHEMBL1835117
• Targinine [BAN]
• NG-monomethyl-L-argine
• L-NG-Monomethylarginine
• H-Arg(Me)-OH acetate salt
• L-NMA
• L-NMMA;Tilarginine;Targinine
• NCGC00024780-01
• NCGC00024780-04
• UNII-27JT06E6GR
• DTXSID3040560
• N(sup G)-Monomethyl-L-arginine
• N(5)-(metilamidino)-L-ornitina
• N5-(N-methylcarbamimidoyl)-L-ornithine
• Tocris-0771
• 8-monomethyl l-arginine
• 2-Amino-5-(N''-methyl-guanidino)-pentanoic acid
• N5-[Imino(methylamino)methyl]-L-ornithine
• Spectrum3_001937
• Spectrum3_001957
• Lopac-M-7033
• n-omega-methyl-l-arginine
• N omega-methyl-L-arginine
• N|O-Monomethyl-L-arginine
• targinine (deprecated INN)
• N(G)-monomethyl L-arginine
• TILARGININE [MART.]
• Lopac0_000750
• BSPBio_003537
• BSPBio_003557
• NMMA, 2
• N(G)-mono-methyl-L-arginine
• L-N.gamma.-Monomethylarginine
• N-gamma-monomethyl-L-arginine
• SCHEMBL315843
• SCHEMBL349879
• NG-METHYLARGININE [MI]
• acide (2S)-2-amino-5-(3-methylguanidino)pentanoique
• orb1701519
• SCHEMBL1736031
• BDBM92900
• CHEBI:28229
• GTPL11467
• KBio3_002795
• KBio3_002876
• CHEBI:124959
• (2S)-2-amino-5-{[imino(methylamino)methyl]amino}pentanoic acid
• BDBM50230993
• BDBM50441055
• EBC-26165
• AKOS022181072
• Ornithine, N5-(methylamidino)-, L-
• CCG-204835
• DB11815
• N(sup 6)-(Methylamidino)-L-ornithine
• SDCCGSBI-0050728.P002
• NCGC00015698-01
• NCGC00024780-02
• NCGC00024780-03
• NCGC00024780-08
• NCGC00178003-01
• HY-18732
• CS-0014212
• NS00068533
• L-Ornithine, N5-(imino(methylamino)methyl)-
• C03884
• G78334
• (S)-2-Amino-5-(3-methylguanidino)pentanoicacid
• EN300-8092850
• (S)-2-amino-5-(2-methylguanidino)pentanoic acid
• BRD-K59506194-015-04-9
• (2S)-2-amino-5-(3-methylcarbamimidamido)pentanoic acid
• (R)-2-Amino-5-(N''-methyl-guanidino)-pentanoic acid
• (S)-2-Amino-5-(N''-methyl-guanidino)-pentanoic acid
• L-ORNITHINE, N(SUP 5)-(IMINO(METHYLAMINO)METHYL)-
• (2S)-2-AMINO-5-((METHYLCARBAMIMIDOYL)AMINO)PENTANOIC ACID

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9058	90.58%
Caco-2	-	0.6538	65.38%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Lysosomes	0.4790	47.90%
OATP2B1 inhibitior	-	0.8455	84.55%
OATP1B1 inhibitior	+	0.9606	96.06%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9458	94.58%
P-glycoprotein inhibitior	-	0.9862	98.62%
P-glycoprotein substrate	-	0.6460	64.60%
CYP3A4 substrate	-	0.6415	64.15%
CYP2C9 substrate	-	0.5960	59.60%
CYP2D6 substrate	-	0.7636	76.36%
CYP3A4 inhibition	-	0.8688	86.88%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9893	98.93%
CYP inhibitory promiscuity	-	0.9937	99.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6273	62.73%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9610	96.10%
Skin irritation	-	0.7738	77.38%
Skin corrosion	-	0.8101	81.01%
Ames mutagenesis	+	0.5230	52.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.6237	62.37%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8374	83.74%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7523	75.23%
Acute Oral Toxicity (c)	IV	0.4956	49.56%
Estrogen receptor binding	-	0.8172	81.72%
Androgen receptor binding	-	0.7667	76.67%
Thyroid receptor binding	-	0.6886	68.86%
Glucocorticoid receptor binding	-	0.8061	80.61%
Aromatase binding	-	0.7727	77.27%
PPAR gamma	-	0.7140	71.40%
Honey bee toxicity	-	0.9611	96.11%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	-	0.9747	97.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.68%	98.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.75%	92.29%
CHEMBL4040	P28482	MAP kinase ERK2	91.35%	83.82%
CHEMBL2514	O95665	Neurotensin receptor 2	89.17%	100.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	89.04%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.43%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.61%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.42%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.33%	91.11%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.20%	97.29%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.10%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.63%	94.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.97%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.18%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.71%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.90%	97.21%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	82.77%	94.01%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.35%	95.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.01%	98.75%
CHEMBL221	P23219	Cyclooxygenase-1	80.34%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 132862
• LOTUS: LTS0058526
• wikiData: Q99615184