Nicotinamide adenine dinucleotide

Nicotinamide adenine dinucleotide

Names
Other names Diphosphopyridine nucleotide (DPN+), Coenzyme I
Identifiers
CAS Number	53-84-9 Y 53-59-8 (phosphate) Y 58-68-4 (NADH) Y
3D model (JSmol)	NAD+: Interactive image NADH: Interactive image
ChEBI	CHEBI:16908 N
ChEMBL	ChEMBL1628272 N
ChemSpider	5681 Y
DrugBank	DB00157 Y
ECHA InfoCard	100.000.169
IUPHAR/BPS	2451
KEGG	C00003 N
PubChem CID	925
RTECS number	UU3450000
UNII	0U46U6E8UK Y BY8P107XEP (phosphate) Y 4J24DQ0916 (NADH) Y
InChI 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 Y Key: BAWFJGJZGIEFAR-NNYOXOHSSA-N Y 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
SMILES 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
Chemical formula	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)	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 YN ?) Infobox references

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.