Back ثنائي نوكليوتيد الأدنين وأميد النيكوتين Arabic نیکوتین‌آمید آدنین دی‌نوکلئوتید AZB НАД Bulgarian Nikotinamid adenin dinukleotid BS Dinucleòtid de nicotinamida i adenina Catalan Nikotinamidadenindinukleotid Czech Deuniwcleotid Adenin Nicotinamid (NAD) Welsh Nikotinamidadenindinukleotid Danish Nicotinamidadenindinukleotid German NADH Esperanto

Nicotinamide adenine dinucleotide

"NAD(P)+" and "NAD(P)H" redirect here. For the phosphates (NADP+/NADPH), see Nicotinamide adenine dinucleotide phosphate.

Nicotinamide adenine dinucleotide
Skeletal formula of the oxidized form
Ball-and-stick model of the oxidized form
Names
Other names
Diphosphopyridine nucleotide (DPN+), Coenzyme I
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.169 Edit this at Wikidata
KEGG
RTECS number
  • UU3450000
UNII
  • InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1 checkY
    Key: BAWFJGJZGIEFAR-NNYOXOHSSA-N checkY
  • InChI=1/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
    Key: BAWFJGJZGIEFAR-NNYOXOHSBR
  • NAD+: O=C(N)c1ccc[n+](c1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP([O-])(=O)OP(=O)([O-])OC[C@H]5O[C@@H](n4cnc3c(ncnc34)N)[C@H](O)[C@@H]5O
  • NADH: O=C(N)C1CC=C[N](C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP([O-])(=O)OP(=O)([O-])OC[C@H]5O[C@@H](n4cnc3c(ncnc34)N)[C@H](O)[C@@H]5O
Properties
C21H28N7O14P2[1][2]
Molar mass 663.43 g/mol
Appearance White powder
Melting point 160 °C (320 °F; 433 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Not hazardous
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism.[3] Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other, nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen), respectively.

In cellular metabolism, NAD is involved in redox reactions, carrying electrons from one reaction to another, so it is found in two forms: NAD+ is an oxidizing agent, accepting electrons from other molecules and becoming reduced; with H+, this reaction forms NADH, which can be used as a reducing agent to donate electrons. These electron transfer reactions are the main function of NAD. It is also used in other cellular processes, most notably as a substrate of enzymes in adding or removing chemical groups to or from proteins, in posttranslational modifications. Because of the importance of these functions, the enzymes involved in NAD metabolism are targets for drug discovery.

In organisms, NAD can be synthesized from simple building-blocks (de novo) from either tryptophan or aspartic acid, each a case of an amino acid. Alternatively, more complex components of the coenzymes are taken up from nutritive compounds such as niacin; similar compounds are produced by reactions that break down the structure of NAD, providing a salvage pathway that recycles them back into their respective active form.

Some NAD is converted into the coenzyme nicotinamide adenine dinucleotide phosphate (NADP), whose chemistry largely parallels that of NAD, though its predominant role is as a coenzyme in anabolic metabolism.

In the name NAD+, the superscripted plus sign indicates the positive formal charge on one of its nitrogen atoms.

  1. ^ "NAD+ | C21H28N7O14P2 | ChemSpider". www.chemspider.com.
  2. ^ "Nicotinamide-Adenine-Dinucleotide". pubchem.ncbi.nlm.nih.gov.
  3. ^ Nelson, David L.; Cox, Michael M. (2005). Principles of Biochemistry (4th ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.

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