(2S)-2-amino-N-[(1S)-3-amino-1-carbamoylpropyl]-5-(3-nitrocarbamimidamido)pentanamide; bis(trifluoroacetic acid)

• ChemBase ID: 153179
• Molecular Formular: C14H24F6N8O8
• Molecular Mass: 546.3795792
• Monoisotopic Mass: 546.16212909
• SMILES: C(C[C@@H](C(=O)N[C@@H](CCN)C(=O)N)N)CNC(=N)N[N+](=O)[O-].C(=O)(C(F)(F)F)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCC[C@@H](C(=O)N)NC(=O)[C@H](CCCNC(=N)N[N+](=O)[O-])N
• InChI: InChI=1S/C10H22N8O4.2C2HF3O2/c11-4-3-7(8(13)19)16-9(20)6(12)2-1-5-15-10(14)17-18(21)22;2*3-2(4,5)1(6)7/h6-7H,1-5,11-12H2,(H2,13,19)(H,16,20)(H3,14,15,17);2*(H,6,7)/t6-,7-;;/m0../s1
• InChIKey: FUXDQBQLZUYRNL-JFYKYWLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-N-[(1S)-3-amino-1-carbamoylpropyl]-5-(3-nitrocarbamimidamido)pentanamide; bis(trifluoroacetic acid)
• IUPAC Traditional name: (2S)-2-amino-N-[(1S)-3-amino-1-carbamoylpropyl]-5-(3-nitrocarbamimidamido)pentanamide; bis(trifluoroacetic acid)
• Synonyms: (2S)-2-amino-N-[(1S)-3-amino-1-(aminocarbonyl)propyl]-5-[[amino(nitroamino)methyl]amino]-pentamide di(trifluoroacetate) salt; L-Nω-Nitroarginine-2,4-L-diaminobutyric amide di(trifluoroacetate) salt

Database IDs

• CAS Number: 244185-39-5
• MDL Number: MFCD05865237
• PubChem SID: 162247318
• PubChem CID: 49861985

CALCULATED PROPERTIES

• Acid pKa: 10.147286
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -9.284197
• LogD (pH = 7.4): -6.1737056
• Log P: -3.8742666
• Molar Refractivity: 88.0956 cm^3
• Polarizability: 29.662966 Å^3
• Polar Surface Area: 217.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C14H24N8O8F6

DETAILS

Sigma Aldrich - N3411

Biochem/physiol Actions
Potent and highly selective inhibitor of nNOS (neuronal nitric oxide synthase).