CHEBI:16908 - NADH

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ChEBI Name NADH
ChEBI ID CHEBI:16908
Definition A coenzyme found in all living cells; consists of two nucleotides joined through their 5'-phosphate groups, with one nucleotide containing an adenine base and the other containing nicotinamide.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44216, CHEBI:7423, CHEBI:13395, CHEBI:13396, CHEBI:21902
Supplier Information ChemicalBook:CB6875459, eMolecules:36366750, ZINC000008215403
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Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. 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 nicotinic acid; 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. A biological coenzyme that acts as an electron carrier in enzymatic reactions. NADP is a reducing agent in anabolic reactions like the Calvin cycle and lipid and nucleic acid syntheses. NADP exists in two forms: NADP+, the oxidized form, and NADPH, the reduced form. NADP is similar to nicotinamide adenine dinucleotide (NAD), but NADP has a phosphate group at the C-2′ position of the adenosyl.
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Formula C21H29N7O14P2
Net Charge 0
Average Mass 665.44126
Monoisotopic Mass 665.12477
InChI InChI=1S/C21H29N7O14P2/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/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKey BOPGDPNILDQYTO-NNYOXOHSSA-N
SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
(via NAD )
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via NAD(P) )
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ChEBI Ontology
Outgoing NADH (CHEBI:16908) has role cofactor (CHEBI:23357)
NADH (CHEBI:16908) has role fundamental metabolite (CHEBI:78675)
NADH (CHEBI:16908) is a NAD (CHEBI:13389)
NADH (CHEBI:16908) is a NAD(P)H (CHEBI:13392)
NADH (CHEBI:16908) is conjugate acid of NADH(2−) (CHEBI:57945)
Incoming (4S)-4-(2-propylisonicotinoyl)nicotinamide adenine dinucleotide (CHEBI:44608) has functional parent NADH (CHEBI:16908)
(S)-NADHX (CHEBI:44236) has functional parent NADH (CHEBI:16908)
(R)-NADHX (CHEBI:134125) has functional parent NADH (CHEBI:16908)
AcNADH (CHEBI:74521) has functional parent NADH (CHEBI:16908)
NADH(2−) (CHEBI:57945) is conjugate base of NADH (CHEBI:16908)
IUPAC Name
adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}
Synonyms Sources
1,4-DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE PDBeChem
DPNH KEGG COMPOUND
NADH KEGG COMPOUND
nicotinamide adenine dinucleotide (reduced) ChEBI
Reduced nicotinamide adenine dinucleotide KEGG COMPOUND
Manual Xrefs Databases
C00004 KEGG COMPOUND
C00019343 KNApSAcK
DB00157 DrugBank
HMDB0001487 HMDB
MOL000027 COMe
NAI PDBeChem
Nicotinamide_adenine_dinucleotide Wikipedia
View more database links
Registry Numbers Types Sources
544241 Gmelin Registry Number Gmelin
58-68-4 CAS Registry Number KEGG COMPOUND
58-68-4 CAS Registry Number ChemIDplus
79324 Beilstein Registry Number Beilstein
79324 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
26 July 2019