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Human Metabolome Database Version 3.5

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Showing metabocard for Nicotinamide ribotide (HMDB00229)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:07 -0700
HMDB ID HMDB00229
Secondary Accession Numbers None
Metabolite Identification
Common Name Nicotinamide ribotide
Description Nicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Mammals predominantly use nicotinamide rather than nicotinic acid as a precursor for NAD biosynthesis. Instead of the deamidation to nicotinic acid, nicotinamide is directly converted to NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), which is a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction NMN + ATP <=> Nicotinamide adenine dinucleotide (NAD) + PPi, representing the final step in the biosynthesis of NAD. NAD is a molecule that plays a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis. Circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171 Link_out, 17983582 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium hydroxide inner salt
  2. 3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt
  3. 3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium hydroxide inner salt
  4. 3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt
  5. 3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  6. 3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt
  7. b-D-NMN
  8. b-NMN
  9. beta-delta-NMN
  10. beta-NMN
  11. Nicotinamide D-ribonucleotide
  12. Nicotinamide mononucleotide
  13. Nicotinamide ribonucleoside 5'-phosphate
  14. Nicotinamide ribonucleotide
  15. NMN
Chemical Formula C11H15N2O8P
Average Molecular Weight 334.2192
Monoisotopic Molecular Weight 334.056601978
IUPAC Name 3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1$l^{5}-pyridin-1-ylium
Traditional IUPAC Name nmn zwitterion
CAS Registry Number 1094-61-7
SMILES NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O
InChI Identifier 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)/t7-,8-,9-,11-/m1/s1
InChI Key DAYLJWODMCOQEW-TURQNECASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyridine Nucleotides
Sub Class Nicotinamide Nucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Organic Compounds
  • nicotinamide mononucleotide(ChEBI)
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Glycosyl Compound
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Primary Carboxylic Acid Amide
  • Pyridine
  • Pyridinium
  • Saccharide
  • Secondary Alcohol
Direct Parent Nicotinamide Nucleotides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.16 g/L ALOGPS
LogP -1.53 ALOGPS
LogP -6.2 ChemAxon
LogS -1.97 ALOGPS
pKa (strongest acidic) 1.21 ChemAxon
pKa (strongest basic) -2.2 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 166.25 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 70.59 ChemAxon
Polarizability 28.78 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Placenta
Pathways
Name SMPDB Link KEGG Link
Nicotinate and Nicotinamide Metabolism SMP00048 map00760 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
66.67 - 133.33 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
133.33 - 600 umol/mmol creatinine Adult (>18 years old) Both Sodium nitrate doses at 10 mg Not Available
Associated Disorders and Diseases
Disease References
Sodium nitrate consumption
  • Jansen EH, van den Berg RH, Boink AB, Hegger C, Meulenbelt J: A new physiological biomarker for nitrate exposure in humans. Toxicol Lett. 1995 May;77(1-3):265-9. Pubmed: 7618150 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021912
    KNApSAcK ID Not Available
    Chemspider ID 13553 Link_out
    KEGG Compound ID C00455 Link_out
    BioCyc ID NICOTINAMIDE_NUCLEOTIDE Link_out
    BiGG ID 35022 Link_out
    Wikipedia Link Not Available
    NuGOwiki Link HMDB00229 Link_out
    Metagene Link HMDB00229 Link_out
    METLIN ID 5238 Link_out
    PubChem Compound 14180 Link_out
    PDB ID Not Available
    ChEBI ID 16171 Link_out
    References
    Synthesis Reference Liu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides & Nucleotides (1994), 13(5), 1215-16.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
    2. Schuberth J: Volatile compounds detected in blood of drunk drivers by headspace/capillary gas chromatography/ion trap mass spectrometry. Biol Mass Spectrom. 1991 Nov;20(11):699-702. Pubmed: 1799580 Link_out
    3. Emanuelli M, Raffaelli N, Amici A, Balducci E, Natalini P, Ruggieri S, Magni G: The antitumor drug, 1,3-bis(2-chloroethyl)-1-nitroso-urea, inactivates human nicotinamide mononucleotide adenylyltransferase. Biochem Pharmacol. 1995 Feb 14;49(4):575-9. Pubmed: 7872964 Link_out
    4. Moriya F, Hashimoto Y: Postmortem production of ethanol and n-propanol in the brain of drowned persons. Am J Forensic Med Pathol. 2004 Jun;25(2):131-3. Pubmed: 15166764 Link_out
    Enzymes
    Name: Cytosolic 5'-nucleotidase 1B
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1B
    Uniprot ID: Q96P26 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytosolic 5'-nucleotidase 1A
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1A
    Uniprot ID: Q9BXI3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 5'(3')-deoxyribonucleotidase, cytosolic type
    Reactions:
      Gene Name: NT5C
      Uniprot ID: Q8TCD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, mitochondrial
      Reactions:
        Gene Name: NT5M
        Uniprot ID: Q9NPB1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
        Reactions:
        • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
        Gene Name: ENPP1
        Uniprot ID: P22413 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 3
        Reactions:
        • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
        Gene Name: ENPP3
        Uniprot ID: O14638 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Nicotinamide mononucleotide adenylyltransferase 1
        Reactions:
        • ATP + nicotinate ribonucleotide = diphosphate + deamido-NAD+ [RN:R03005]
        Gene Name: NMNAT1
        Uniprot ID: Q9HAN9 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Nicotinamide mononucleotide adenylyltransferase 3
        Reactions:
        • ATP + nicotinate ribonucleotide = diphosphate + deamido-NAD+ [RN:R03005]
        Gene Name: NMNAT3
        Uniprot ID: Q96T66 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Nicotinamide mononucleotide adenylyltransferase 2
        Reactions:
        • ATP + nicotinate ribonucleotide = diphosphate + deamido-NAD+ [RN:R03005]
        Gene Name: NMNAT2
        Uniprot ID: Q9BZQ4 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytosolic 5'-nucleotidase 3
        Reactions:
        • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
        Gene Name: NT5C3
        Uniprot ID: Q9H0P0 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Peroxisomal NADH pyrophosphatase NUDT12
        Reactions:
        • NAD+ + H2O = AMP + NMN [RN:R00103]
        Gene Name: NUDT12
        Uniprot ID: Q9BQG2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Nicotinamide phosphoribosyltransferase
        Reactions:
        • nicotinamide D-ribonucleotide + diphosphate = nicotinamide + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01271]
        Gene Name: NAMPT
        Uniprot ID: P43490 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA