Show more...
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:49 UTC
Update Date2024-10-15 18:17:31 UTC
Metabolite IDMMDBc0000572
Metabolite Identification
Common NameSymmetric dimethylarginine
DescriptionSymmetric dimethylarginine, also known as N,n'-dimethylarginine or SDMA, is a L-arginine derivative having two methyl groups at the N(omega)- and N'(omega)-positions It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of guanidines, a non-proteinogenic L-alpha-amino acid, a L-arginine derivative and a dimethylarginine. It is a tautomer of a N(omega),N'(omega)-dimethyl-L-arginine zwitterion. It 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. Symmetric dimethylarginine is a drug. Outside of the human body, symmetric dimethylarginine has been detected, but not quantified in pulses. Symmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of Symmetric dimethylarginine occur in patients with vascular disease, especially suffering end-stage renal disease.
Structure
Synonyms
Molecular FormulaC8H18N4O2
Average Mass202.2541
Monoisotopic Mass202.14297584
IUPAC Name(2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid
Traditional NameN3, N4-dimethylarginine
CAS Registry NumberNot Available
SMILES
CN\C(NCCC[C@H](N)C(O)=O)=N/C
InChI Identifier
InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1
InChI KeyHVPFXCBJHIIJGS-LURJTMIESA-N