(2S)-2-amino-5-{[bis(methylamino)methylidene]amino}pentanoic acid; bis(4-[(E)-2-(4-hydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid)

• ChemBase ID: 133807
• Molecular Formular: C32H38N8O10S2
• Molecular Mass: 758.82172
• Monoisotopic Mass: 758.21523146
• SMILES: CNC(=NCCC[C@H](N)C(=O)O)NC.c1c(ccc(c1)O)/N=N/c1ccc(cc1)S(=O)(=O)O.c1c(ccc(c1)O)/N=N/c1ccc(cc1)S(=O)(=O)O
• Canonical SMILES: Oc1ccc(cc1)/N=N/c1ccc(cc1)S(=O)(=O)O.Oc1ccc(cc1)/N=N/c1ccc(cc1)S(=O)(=O)O.CNC(=NCCC[C@@H](C(=O)O)N)NC
• InChI: InChI=1S/2C12H10N2O4S.C8H18N4O2/c2*15-11-5-1-9(2-6-11)13-14-10-3-7-12(8-4-10)19(16,17)18;1-10-8(11-2)12-5-3-4-6(9)7(13)14/h2*1-8,15H,(H,16,17,18);6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/b2*14-13+;/t;;6-/m..0/s1
• InChIKey: HISUXCNNXYEHER-YJSASASGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-{[bis(methylamino)methylidene]amino}pentanoic acid; bis(4-[(E)-2-(4-hydroxyphenyl)diazen-1-yl]benzene-1-sulfonic acid)
• IUPAC Traditional name: (2S)-2-amino-5-{[bis(methylamino)methylidene]amino}pentanoic acid; bis(4-[(E)-2-(4-hydroxyphenyl)diazen-1-yl]benzenesulfonic acid)
• Synonyms: SDMA; NG,NG′-Dimethyl-L-arginine di(p-hydroxyazobenzene-p′-sulfonate) salt

Database IDs

• CAS Number: 30344-00-4(freebase)
• PubChem SID: 162228084
• PubChem CID: 71308719

CALCULATED PROPERTIES

• Acid pKa: -2.6949127
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.87956494
• LogD (pH = 7.4): 0.8398681
• Log P: 1.3733613
• Molar Refractivity: 72.9804 cm^3
• Polarizability: 26.806908 Å^3
• Polar Surface Area: 99.32 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99% (TLC)

DETAILS

Sigma Aldrich - D0390

Application
Plasma sym-dimethylarginine has been considered a marker of hepatic and renal dysfunction. A sensitive LC-MS method for identifying arginine, and both asym- and sym-dimethylarginine in plasma and urine samples has been developed.1