3-carbamoyl-1-{5-[({[(3,4-dihydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl)methoxy](hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1λ5-pyridin-1-ylium

• ChemBase ID: 155503
• Molecular Formular: C23H27N7O14P2
• Molecular Mass: 687.446502
• Monoisotopic Mass: 687.10912184
• SMILES: c1cn2cnc3c(c2n1)ncn3C1C(C(C(O1)COP(=O)(O)OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=O)N)O)O)O)O
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OCC2OC(C(C2O)O)[n+]2cccc(c2)C(=O)N)[O-])O)OC(C1O)n1cnc2c1ncn1c2ncc1
• InChI: InChI=1S/C23H27N7O14P2/c24-19(35)11-2-1-4-28(6-11)22-17(33)15(31)12(42-22)7-40-45(36,37)44-46(38,39)41-8-13-16(32)18(34)23(43-13)30-10-26-14-20-25-3-5-29(20)9-27-21(14)30/h1-6,9-10,12-13,15-18,22-23,31-34H,7-8H2,(H3-,24,35,36,37,38,39)
• InChIKey: JCDBQDNBEQHDHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoyl-1-{5-[({[(3,4-dihydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl)methoxy](hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-carbamoyl-1-[5-({[(3,4-dihydroxy-5-{imidazo[2,1-f]purin-3-yl}oxolan-2-yl)methoxy(hydroxy)phosphoryl phosphonato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: ε-NAD; 1,N6-Etheno NAD; 1,N6-Ethenonicotinamide adenine dinucleotide; Nicotinamide 1,N6-ethenoadenine dinucleotide

Database IDs

• CAS Number: 38806-38-1
• MDL Number: MFCD00063546
• PubChem SID: 24897579; 162249641
• PubChem CID: 57349623

CALCULATED PROPERTIES

• Acid pKa: 1.8613118
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -11.328179
• LogD (pH = 7.4): -11.659365
• Log P: -10.198208
• Molar Refractivity: 147.2714 cm^3
• Polarizability: 58.869633 Å^3
• Polar Surface Area: 299.48 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C23H27N7O14P2

DETAILS

Sigma Aldrich - N2630

Application
Nicotinamide 1,N6-ethenoadenine dinucleotide (ε-NAD) is an NAD fluorescent analog (fluorophore) that may be used to study ADP-ribosylation reactions and the structure/kinetics of NAD+ binding enzymes.
Other Notes
Analog of β-NAD