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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:30:17 UTC
Update Date2020-02-26 21:43:35 UTC
HMDB IDHMDB0029416
Secondary Accession Numbers
  • HMDB29416
Metabolite Identification
Common NameL-Targinine
DescriptionL-Targinine, also known as L-NMMA or targinina, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Targinine is a very strong basic compound (based on its pKa). Outside of the human body, L-Targinine has been detected, but not quantified in, pulses. This could make L-targinine a potential biomarker for the consumption of these foods. L-Targinine has been investigated for the basic science, treatment, and diagnostic of Obesity, Type 2 Diabetes, Ocular Physiology, and Regional Blood Flow.
Structure
Data?1582753415
Synonyms
ValueSource
Acide (2S)-2-amino-5-(3-methylguanidino)pentanoiqueChEBI
L-MonomethylarginineChEBI
L-NMMAChEBI
N-Monomethyl-L-arginineChEBI
N(5)-(Methylamidino)-L-ornithineChEBI
N(5)-(Metilamidino)-L-ornitinaChEBI
N(g)-Monomethyl-L-arginineChEBI
Ngamma-monomethyl-L-arginineChEBI
Omega-N-methylarginineChEBI
Omega-N-monomethylarginineChEBI
TargininaChEBI
TarginineChEBI
TargininumChEBI
TilargininaChEBI
TilarginineChEBI
TilargininumChEBI
N(5)-(N-Methylcarbamimidoyl)-L-ornithineHMDB
N(5)-[Imino(methylamino)methyl]-L-ornithineHMDB
N(Omega)-methyl-L-arginineHMDB
N-Methyl-L-arginineHMDB
N-Omega-methyl-L-arginineHMDB
N-Omega-monomethyl-L-arginineHMDB
N5-(N-Methylcarbamimidoyl)-L-ornithineHMDB
NG-Monomethyl-L-argineHMDB
L NG Monomethyl arginineHMDB
NG Monomethyl L arginineHMDB
Omega N methylarginineHMDB
Arginine, L-NG-monomethylHMDB
N(g)-MethylarginineHMDB
N(g)-Monomethyl-D-arginineHMDB
N(g)-MonomethylarginineHMDB
N(Omega)-monomethyl-L-arginineHMDB
D-NMMAHMDB
L MonomethylarginineHMDB
L-NG-Monomethyl arginineHMDB
NG-Monomethyl-L-arginineHMDB
Chemical FormulaC7H16N4O2
Average Molecular Weight188.2275
Monoisotopic Molecular Weight188.127325776
IUPAC Name(2S)-2-amino-5-(3-methylcarbamimidamido)pentanoic acid
Traditional NameNG monomethyl L arginine
CAS Registry Number17035-90-4
SMILES
CNC(=N)NCCC[C@H](N)C(O)=O
InChI Identifier
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 KeyNTNWOCRCBQPEKQ-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentArginine and derivatives
Alternative Parents
Substituents
  • Arginine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.45 g/LALOGPS
logP-3.5ALOGPS
logP-2.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.48ChemAxon
pKa (Strongest Basic)12.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area111.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.7 m³·mol⁻¹ChemAxon
Polarizability20.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-9300000000-8a5d10c2c8d6cd8eae8eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9210000000-c205856837ac75413884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0076-1900000000-b304f22c29cac910afdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9800000000-e1e925df5f5a69746f04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-23540f46e00006c9651cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-87d59411066c5f0db9e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9700000000-a2bcbbf60caf5fc66643Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-0cc6ad3e3fb7ee0fb63dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11815
Phenol Explorer Compound IDNot Available
FooDB IDFDB000510
KNApSAcK IDNot Available
Chemspider ID117259
KEGG Compound IDC03884
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylarginine
METLIN IDNot Available
PubChem Compound132862
PDB IDNMM
ChEBI ID28229
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .