Showing Compound Nicotinamide ribotide (FDB021912)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:02 UTC

Update date

2015-10-09 22:30:48 UTC

Primary ID

FDB021912

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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), 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, a molecule playing a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171, 17983582) [HMDB]

CAS Number

1094-61-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Search:

Synonym	Source
(6S)-Tetrahydrofolate	HMDB
(6S)-Tetrahydrofolic acid	HMDB
1,2-Diphenylethane-1,2-dione	HMDB
1,4 Butanediamine	HMDB
1,4 Diaminobutane	HMDB
1,4-Butanediamine	HMDB
1,4-Butanediammonium	HMDB
1,4-Butylenediamine	HMDB
1,4-DIAMINOBUTANE	HMDB
1,4-Tetramethylenediamine	HMDB

Showing 1 to 10 of 98 entries

Predicted Properties

Property	Value	Source
Water Solubility	4.16 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-6.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	166.25 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.59 m³·mol⁻¹	ChemAxon
Polarizability	28.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H15N2O8P

IUPAC name

3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium

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

Isomeric SMILES

NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O

Average Molecular Weight

334.2192

Monoisotopic Molecular Weight

334.056601978

Classification

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyridine nucleotides

Sub Class

Nicotinamide nucleotides

Direct Parent

Nicotinamide nucleotides

Alternative Parents

Substituents

Nicotinamide-nucleotide
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Monosaccharide phosphate
Nicotinamide
Pyridine carboxylic acid or derivatives
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyridinium
Pyridine
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
1,2-diol
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Azacycle
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic zwitterion
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nicotinamide mononucleotide (CHEBI:16171 )

Ontology

Physiological effect

Health effect:

Health condition:

Sodium nitrate consumption

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Nicotinamide ribotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-8902000000-75d46c23151f03298e05	Spectrum
Predicted GC-MS	Nicotinamide ribotide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-4920300000-f0eec1327b9e3e217fdd	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1931000000-5aa0e5ba467b6bdbb57f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dj-6920000000-4720b1b8ab108dc1b499	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00mk-8903000000-042bd96d57e63adafe44	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-3900000000-013c2f02e48342e61b5e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-3900000000-013c2f02e48342e61b5e	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1109000000-7e48df4297f6933ffc64	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-7419000000-c70e04daa2249a30318c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9600000000-ec07884c9a438ebdba5a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1009000000-623a45d318f08c622565	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9002000000-a9b586e58b5858c6d213	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0032-9000000000-3fde5442f77c9f4b54b3	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum