Showing Compound Card for Symmetric dimethylarginine (CDB006326)

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Record Information
Version1.0
Created at2020-09-11 15:49:11 UTC
Updated at2020-11-18 16:40:18 UTC
CannabisDB IDCDB006326
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSymmetric dimethylarginine
DescriptionSymmetric dimethylarginine, also known as N(g1),N(g2)-dimethylarginine or SDMA, 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 has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and pulses. This could make symmetric dimethylarginine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Symmetric dimethylarginine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoic acidChEBI
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoic acidChEBI
Guanidino-N(1),N(2)-dimethylarginineChEBI
N(g1),N(g2)-DimethylarginineChEBI
N,N'-dimethylarginineChEBI
N(3),N(4)-Dimethyl-L-arginineChEBI
N(3),N(4)-DimethylarginineChEBI
N5-((Methylamino)(methylimino)methyl)-L-ornithineChEBI
N(5)-(N,N'-dimethylamidino)-L-ornithineChEBI
N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithineChEBI
N(5)-[Bis(methylamino)methylene]-L-ornithineChEBI
N(g),N'(g)-dimethyl-L-arginineChEBI
N(g),N'(g)-dimethylarginineChEBI
SDMAChEBI
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoateGenerator
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoateGenerator
N5-(N,N'-dimethylamidino)-L-ornithineHMDB
N5-[Bis(methylamino)methylene]-L-ornithineHMDB
NG,N'G-dimethyl-L-arginineHMDB, MeSH
NG,N'G-dimethylarginineHMDB
NG,NG'-dimethylarginineHMDB
Omega-N(g),n'(g)-dimethylarginineMeSH, HMDB
SDMA arginineMeSH, HMDB
Chemical FormulaC8H18N4O2
Average Molecular Weight202.2541
Monoisotopic Molecular Weight202.14297584
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
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
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Imine
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
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
logP-2.9ALOGPS
logP-2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)12.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.18 m³·mol⁻¹ChemAxon
Polarizability22.22 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSymmetric dimethylarginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kfx-9600000000-f6c986d30ea287579a78Spectrum
Predicted GC-MSSymmetric dimethylarginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fkc-9720000000-0f297fd1183458956770Spectrum
Predicted GC-MSSymmetric dimethylarginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSymmetric dimethylarginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9600000000-a9cb6507d9fe3ffb39aa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-053r-3910000000-1a8526e47c9af75d4cc92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9400000000-777d41b210dd091439b42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1930000000-98ffa2f50a3e5ee90e102016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-8900000000-eccaa3c6c71a7aab8dd32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-fd3f3045e508262e68be2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3390000000-ec3717ed507fec5312022016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9520000000-06ed24b7ccb74ccd705b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9000000000-40bdb35b370bc3317a552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2190000000-1ff257e4be06b9702e652021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-b9dfe8a8d6f891dcecbf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-926c9fc48c09f40304992021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-1590000000-567e7d20ebbf052f8d392021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900000000-84e3189b175eab73e2c52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c8ec00d7abbc06aa7e4c2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0176 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0172 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0129 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0228 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0199 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.02512 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0003334
DrugBank IDDB02302
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000509
KNApSAcK IDC00052415
Chemspider ID147942
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6891
PubChem Compound169148
PDB IDNot Available
ChEBI ID25682
References
General ReferencesNot Available