Record Information
Version2.0
Creation Date2012-10-10 12:22:43 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23222
Identification
Name:NMN
Description3-Carbamoyl-1-beta-D-ribofuranosyl pyridinium hydroxide-5'phosphate, inner salt. A nucleotide in which the nitrogenous base, nicotinamide, is in beta-N-glycosidic linkage with the C-1 position of D-ribose
Structure
Thumb
Synonyms:
  • β-nicotinamide mononucleotide
  • β-nicotinamide nucleotide
  • β-nicotinamide ribonucleotide
  • NicRN
  • NMN
Chemical Formula:C11H16N2O8P
Weight:Average: 335.2271
Monoisotopic: 335.06442701
InChI Key:DAYLJWODMCOQEW-TURQNECASA-O
InChI:InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/p+1/t7-,8-,9-,11-/m1/s1
CAS number:1094-61-7
IUPAC Name:1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1λ⁵-pyridin-1-ylium
Traditional IUPAC Name:1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1λ⁵-pyridin-1-ylium
SMILES:[H][C@]1(COP(O)(O)=O)O[C@@]([H])([N+]2=CC=CC(=C2)C(O)=N)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyridine nucleotides
Sub ClassNicotinamide nucleotides
Direct ParentNicotinamide nucleotides
Alternative Parents
Substituents
  • Nicotinamide-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Nicotinamide
  • Pyridine carboxylic acid or derivatives
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyridine
  • Pyridinium
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.53 g/LALOGPS
logP-1.5ALOGPS
logP-8.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)6.02ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.41 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.64 m³·mol⁻¹ChemAxon
Polarizability29.35 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
NAD salvagePW000830 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00tb-5902000000-fcee9746cbbfd4c7b910View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9321310000-a76824e42fa52329c65eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1009000000-5f50c20045d0b9493f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-5219000000-3b516421e6f26f4266eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9500000000-4760ef36c1253b7200ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2009000000-388bca4c5bcdaaf421c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9001000000-1dc8f508da2995c85814View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b190037f5b434f05678bView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16171
HMDB IDHMDB00229
Pubchem Compound ID14180
Kegg IDC00455
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNICOTINAMIDE_NUCLEOTIDE
EcoCyc IDNICOTINAMIDE_NUCLEOTIDE
Ligand ExpoNMN

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible adenylation of nicotinate mononucleotide (NaMN) to nicotinic acid adenine dinucleotide (NaAD)
Gene Name:
nadD
Uniprot ID:
P0A752
Molecular weight:
24528
Reactions
ATP + beta-nicotinate-D-ribonucleotide = diphosphate + deamido-NAD(+).
General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of E.coli in stationary growth phase
Gene Name:
surE
Uniprot ID:
P0A840
Molecular weight:
26900
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in catalytic activity
Specific function:
Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
Gene Name:
yjjG
Uniprot ID:
P0A8Y1
Molecular weight:
25300
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in DNA ligase (NAD+) activity
Specific function:
DNA ligase that catalyzes the formation of phosphodiester linkages between 5'-phosphoryl and 3'-hydroxyl groups in double-stranded DNA using NAD as a coenzyme and as the energy source for the reaction. It is essential for DNA replication and repair of damaged DNA
Gene Name:
ligA
Uniprot ID:
P15042
Molecular weight:
73605
Reactions
NAD(+) + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) = AMP + beta-nicotinamide D-ribonucleotide + (deoxyribonucleotide)(n+m).
General function:
Involved in DNA ligase (NAD+) activity
Specific function:
Catalyzes the formation of phosphodiester linkages between 5'-phosphoryl and 3'-hydroxyl groups in double-stranded DNA using NAD as a coenzyme and as the energy source for the reaction
Gene Name:
ligB
Uniprot ID:
P25772
Molecular weight:
63179
Reactions
NAD(+) + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) = AMP + beta-nicotinamide D-ribonucleotide + (deoxyribonucleotide)(n+m).
General function:
Involved in negative regulation of transcription, DNA-dependent
Specific function:
NadR is bifunctional; it interacts with pnuC at low internal NAD levels, permitting transport of NMN intact into the cell. As NAD levels increase within the cell, the affinity of nadR for the operator regions of nadA, nadB, and pncB increases, repressing the transcription of these genes
Gene Name:
nadR
Uniprot ID:
P27278
Molecular weight:
47346
Reactions
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+).
ATP + N-ribosylnicotinamide = ADP + nicotinamide ribonucleotide.
General function:
Involved in hydrolase activity
Specific function:
NAD(+) + H(2)O = AMP + NMN
Gene Name:
nudC
Uniprot ID:
P32664
Molecular weight:
29689
Reactions
NAD(+) + H(2)O = AMP + NMN.
General function:
pyridine nucleotide biosynthetic process
Specific function:
Has nicotinamidemononucleotide (NMN) aminohydrolase activity, not active on other substrates.
Gene Name:
pncC
Uniprot ID:
P0A6G3
Molecular weight:
17581
Reactions
Beta-nicotinamide D-ribonucleotide + H(2)O = beta-nicotinate D-ribonucleotide + NH(3)