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MetaCyc Compound Class: NAD(P)H

Synonyms: β-NAD(P)H

Superclasses: a nucleic acid component a nucleotide a dinucleotide a dinucleotide electron carrier
a nucleic acid component a nucleotide a dinucleotide electron carrier
a nucleic acid component an oligonucleotide a dinucleotide a dinucleotide electron carrier
a redox electron carrier

Summary:
NAD(P)H is a class of compounds including the instances NADH and NADPH.

NAD(P)H compound structure

Instances:
NADH ,
NADPH

SMILES: C1(=C(CC=CN1C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O[R])C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5))C(N)=O)

Unification Links: ChEBI:13392

Reactions known to consume the compound:

1,4-dichlorobenzene degradation , 2,4,5-trichlorophenoxyacetate degradation , 2,4,6-trichlorophenol degradation , 3,4,6-trichlorocatechol degradation , 3,5-dichlorocatechol degradation , 3-chlorocatechol degradation I (ortho) , 3-chlorocatechol degradation II (ortho) , 4,5-dichlorocatechol degradation , 4-aminophenol degradation , 4-chlorocatechol degradation , 4-hydroxyacetophenone degradation , 4-sulfocatechol degradation , chlorosalicylate degradation , γ-hexachlorocyclohexane degradation , pentachlorophenol degradation , resorcinol degradation :
3-oxoadipate + NAD(P)+ ← 2-maleylacetate + NAD(P)H + H+

1,5-anhydrofructose degradation :
1,5-anhydro-D-mannitol + NAD(P)+ ← 1,5-anhydro-D-fructose + NAD(P)H + H+

2'-deoxymugineic acid phytosiderophore biosynthesis :
2'-deoxymugineate + NAD(P)+ ← 3''-deamino-3''-oxonicotianamine + NAD(P)H + H+

2-hydroxyphenazine biosynthesis :
phenazine-1-carboxylate + NAD(P)H + oxygen + H+ → 2-hydroxyphenazine-1-carboxylate + NAD(P)+ + H2O

2-nitrobenzoate degradation II :
anthranilate + NAD(P)H + oxygen + 3 H+ → catechol + CO2 + ammonium + NAD(P)+
2-hydroxylaminobenzoate + NAD(P)H + H+ → anthranilate + NAD(P)+ + H2O

4-nitrobenzoate degradation :
4-nitrobenzoate + 2 NAD(P)H + 2 H+ → 4-hydroxylaminobenzoate + 2 NAD(P)+ + H2O

4-nitrophenol degradation I :
3-oxoadipate + NAD(P)+ ← 2-maleylacetate + NAD(P)H + H+
4-nitrophenol + NAD(P)H + oxygen + H+ → 1,4-benzoquinone + nitrite + NAD(P)+ + H2O

4-nitrophenol degradation II :
3-oxoadipate + NAD(P)+ ← 2-maleylacetate + NAD(P)H + H+
4-nitrocatechol + NAD(P)H + oxygen → 2-hydroxy-1,4-benzoquinone + nitrite + NAD(P)+ + H2O + H+

ajmaline and sarpagine biosynthesis :
10-deoxysarpagine + NAD(P)H + oxygen + H+ → sarpagine + NAD(P)+ + H2O

alginate degradation :
(4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + NAD(P)H + H+ → 2-dehydro-3-deoxy-D-gluconate + NAD(P)+

alkane biosynthesis I :
a long-chain aldehyde + a holo-[acyl-carrier protein] + NAD(P)+ ← a long-chain acyl-[acp] + NAD(P)H + H+

alkylnitronates degradation , nitrate reduction V (assimilatory) :
ammonium + 3 NAD(P)+ + 2 H2O ← nitrite + 3 NAD(P)H + 5 H+

α-cyclopiazonate detoxification :
α-cyclopiazonate + NAD(P)H + H+ + oxygen → 2-oxocyclopiazonate + NAD(P)+ + H2O

anthranilate degradation I (aerobic) , indole-3-acetate degradation VIII (bacterial) :
anthranilate + NAD(P)H + oxygen + 3 H+ → catechol + CO2 + ammonium + NAD(P)+

anthranilate degradation II (aerobic) :
anthraniloyl-CoA + 2 NAD(P)H + oxygen + 2 H+ → 2-amino-5-oxocyclohex-1-enecarboxyl-CoA + 2 NAD(P)+ + H2O

arachidonate biosynthesis I (lower eukaryotes) , arachidonate biosynthesis III (metazoa) :
3-oxo-dihomo γ-linolenoyl-CoA + NAD(P)H + H+ → 3R-hydroxy-dihomo γ-linolenoyl-CoA + NAD(P)+

archaetidylserine and archaetidylethanolamine biosynthesis :
2,3-bis-O-phytanyl-sn-glycerol 1-phosphate + 8 NAD(P)+ ← 2,3-bis-O-(geranylgeranyl)-sn-glycerol 1-phosphate + 8 NAD(P)H + 8 H+

arsenate detoxification III (mycothiol) , mycothiol oxidation :
2 mycothiol + NAD(P)+ ← mycothione + NAD(P)H + H+

aspyridone A biosynthesis :
preaspyridone A + NAD(P)H + H+ + oxygen → 14-hydroxypreaspyridone A + NAD(P)+ + H2O
preaspyridone A + NAD(P)H + oxygen + H+ → aspyridone A + NAD(P)+ + 2 H2O
acetyl-CoA + 3 malonyl-CoA + a holo-[acyl-carrier protein] + 2 S-adenosyl-L-methionine + 4 NAD(P)H + 5 H+ → 4,6-dimethyl-3-oxooctanoyl-ACP + 2 S-adenosyl-L-homocysteine + 3 CO2 + 4 coenzyme A + 4 NAD(P)+ + 2 H2O

aurachin A, B, C and D biosynthesis :
aurachin C epoxide + NAD(P)H + H+ → aurachin B + NAD(P)+ + H2O

Reactions known to produce the compound:

(Z)-phenylmethanethial S-oxide biosynthesis :
phenylmethanesulfenate + NAD(P)+ → (Z)-phenylmethanethial S-oxide + NAD(P)H + H+

4-aminobutyrate degradation III :
succinate semialdehyde + NAD(P)+ + H2O → succinate + NAD(P)H + 2 H+

4-coumarate degradation (anaerobic) :
4-hydroxybenzaldehyde + NAD(P)+ + H2O → 4-hydroxybenzoate + NAD(P)H + 2 H+

abscisic acid biosynthesis shunt :
trans-abscisic alcohol + 2 NAD(P)+ + H2O → 2-trans-abscisate + 2 NAD(P)H + 3 H+
cis-abscisic alcohol + 2 NAD(P)+ + H2O → 2-cis-abscisate + 2 NAD(P)H + 3 H+

acrylate degradation :
3-oxopropanoate + coenzyme A + NAD(P)+ → acetyl-CoA + CO2 + NAD(P)H

allantoin degradation IV (anaerobic) :
S-ureidoglycolate + NAD(P)+ → oxalurate + NAD(P)H + H+

β-alanine biosynthesis I , β-alanine biosynthesis IV :
3-aminopropanal + NAD(P)+ + H2O → β-alanine + NAD(P)H + 2 H+

cholesterol biosynthesis I :
4α-carboxy-5α-cholesta-8,24-dien-3β-ol + NAD(P)+ → 5α-cholesta-8,24-dien-3-one + CO2 + NAD(P)H
4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NAD(P)+ → 3-dehydro-4-methylzymosterol + CO2 + NAD(P)H

cholesterol biosynthesis II (via 24,25-dihydrolanosterol) :
4α-carboxy-4β-methyl-5α-cholesta-8-en-3β-ol + NAD(P)+ → 4α-methyl-5α-cholesta-8-en-3-one + CO2 + NAD(P)H
4α-carboxy-5α-cholesta-8-en-3β-ol + NAD(P)+ → 5α-cholesta-8-en-3-one + CO2 + NAD(P)H

cholesterol biosynthesis III (via desmosterol) :
4α-carboxy-5α-cholesta-8,24-dien-3β-ol + NAD(P)+ → 5α-cholesta-8,24-dien-3-one + CO2 + NAD(P)H
4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol + NAD(P)+ → 3-dehydro-4-methylzymosterol + CO2 + NAD(P)H

dehydro-D-arabinono-1,4-lactone biosynthesis :
D-arabinofuranose + NAD(P)+ → D-arabinono-1,4-lactone + NAD(P)H + H+

ferulate and sinapate biosynthesis :
coniferaldehyde + NAD(P)+ + H2O → ferulate + NAD(P)H + 2 H+

fluorene degradation I :
9-fluorenol + NAD(P)+ → 9-fluorenone + NAD(P)H + H+

heterolactic fermentation :
D-gluconate 6-phosphate + NAD(P)+ → D-ribulose 5-phosphate + CO2 + NAD(P)H

homotaurine degradation :
3-sulfopropanal + NAD(P)+ + H2O → 3-sulfopropanoate + NAD(P)H + 2 H+

isopropylamine degradation :
L-alaninol + NAD(P)+ → L-2-aminopropionaldehyde + NAD(P)H + H+
L-2-aminopropionaldehyde + NAD(P)+ + H2O → L-alanine + NAD(P)H + 2 H+
propanal + NAD(P)+ + H2O → propanoate + NAD(P)H + 2 H+

kanamycin biosynthesis , paromamine biosynthesis I :
2-deoxy-scyllo-inosamine + NAD(P)+ → 3-amino-2,3-dideoxy-scyllo-inosose + NAD(P)H + H+

L-arabinose degradation III :
2,5-dioxopentanoate + NAD(P)+ + H2O → 2-oxoglutarate + NAD(P)H + 2 H+
L-arabinofuranose + NAD(P)+ → L-arabinono-1,4-lactone + NAD(P)H + H+

Reactions known to both consume and produce the compound:

5,6-dimethylbenzimidazole biosynthesis :
FMNH2 + NAD(P)+ ↔ FMN + NAD(P)H + 2 H+

allopregnanolone biosynthesis :
allopregnanolone + NAD(P)+ ↔ 5-α-pregnane-3,20-dione + NAD(P)H + H+

cholate degradation (bacteria, anaerobic) :
choloyl-CoA + NAD(P)+ ↔ 3-oxo-cholyl-CoA + NAD(P)H + H+

formaldehyde assimilation I (serine pathway) :
D-glycerate + NAD(P)+ ↔ hydroxypyruvate + NAD(P)H + H+

formaldehyde oxidation II (glutathione-dependent) :
S-hydroxymethylglutathione + NAD(P)+S-formylglutathione + NAD(P)H + H+

formaldehyde oxidation V (H4MPT pathway) :
5,10-methylene-tetrahydromethanopterin + NAD(P)+ ↔ 5,10-methenyltetrahydromethanopterin + NAD(P)H

GABA shunt , L-glutamate biosynthesis II , L-glutamate degradation X , L-ornithine de novo biosynthesis :
L-glutamate + NAD(P)+ + H2O ↔ 2-oxoglutarate + ammonium + NAD(P)H + H+

glycerol degradation to butanol , pyruvate fermentation to butanol I , pyruvate fermentation to butanol II :
butanal + coenzyme A + NAD(P)+ ↔ butanoyl-CoA + NAD(P)H + H+

hydrogen production VIII :
a plastoquinone + NAD(P)H + H+ ↔ a plastoquinol + NAD(P)+

imidazole-lactate degradation , L-histidine degradation IV :
imidazole-lactate + NAD(P)+ ↔ imidazole-pyruvate + NAD(P)H + H+

L-idonate degradation :
L-idonate + NAD(P)+ ↔ 5-dehydro-D-gluconate + NAD(P)H + H+
D-gluconate + NAD(P)+ ↔ 5-dehydro-D-gluconate + NAD(P)H + H+

L-ornithine degradation II (Stickland reaction) :
(2R,4S)-2, 4-diaminopentanoate + NAD(P)+ + H2O ↔ 2-amino-4-oxopentanoate + ammonium + NAD(P)H + H+

L-sorbose degradation :
keto-L-sorbose 1-phosphate + NAD(P)H + H+ ↔ D-sorbitol 6-phosphate + NAD(P)+

mannitol cycle :
D-mannitol 1-phosphate + NAD(P)+ ↔ β-D-fructofuranose 6-phosphate + NAD(P)H + H+

morphine biosynthesis :
morphine + NAD(P)+ ↔ morphinone + NAD(P)H + H+

Not in pathways:
D-glyceraldehyde 3-phosphate + NAD(P)+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NAD(P)H + H+
NAD(P)+ + H2NAD(P)H + H+
D-glucopyranose + NAD(P)+ ↔ D-glucono-1,5-lactone + NAD(P)H + H+
(2R)-3-sulfolactate + NAD(P)+ ↔ 3-sulfopyruvate + NAD(P)H + H+
(S)-malate + NAD(P)+ ↔ oxaloacetate + NAD(P)H + H+

In Reactions of unknown directionality:

Not in pathways:
16-α-hydroxysteroid + NAD(P)+ = 16-oxosteroid + NAD(P)H + H+
1-indanol + NAD(P)+ = indanone + NAD(P)H + H+
2 coenzyme A + NAD(P)+ = CoA-disulfide + NAD(P)H + H+
a protein dithiol + NAD(P)+ = a protein disulfide + NAD(P)H + H+
an n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
nitrous oxide + NAD(P)+ + H2O = 2 nitric oxide + NAD(P)H + H+
23,24-dihydrocucurbitacin B + NAD(P)+ = cucurbitacin B + NAD(P)H + H+
2-acetamidofluorene + NAD(P)+ + H2O = N-hydroxy-2-acetamidofluorene + NAD(P)H + H+
thiomorpholine-3-carboxylate + NAD(P)+ = 3,4-dehydrothiomorpholine-3-carboxylate + NAD(P)H + 2 H+
3-oxopropanoate + NAD(P)+ + H2O = malonate + NAD(P)H + 2 H+
D-glycerate + CO2 + NAD(P)+ = 2-hydroxy-3-oxosuccinate + NAD(P)H + 2 H+
estradiol-17α + NAD(P)+ = estrone + NAD(P)H + H+
D-mannonate + NAD(P)+ = D-mannuronate + NAD(P)H + H+
D-ribitol 5-phosphate + NAD(P)+ = D-ribulose 5-phosphate + NAD(P)H + H+
2 a reduced rubredoxin + NAD(P)+ + H+ = 2 an oxidized rubredoxin + NAD(P)H
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
nitrite + NAD(P)+ + H2O = nitrate + NAD(P)H + H+
(+)-thujan-3-ol + NAD(P)+ = (+)-thujan-3-one + NAD(P)H + H+
(20S)-17,20-dihydroxypregn-4-en-3-one + NAD(P)+ = 17-α-hydroxyprogesterone + NAD(P)H + H+
5-α-androstan-3α,17β-diol + NAD(P)+ = 5-α-dihydrotestosterone + NAD(P)H + H+
L-quinate + NAD(P)+ = 3-dehydroquinate + NAD(P)H + H+
squalene + NAD(P)+ + diphosphate = presqualene diphosphate + NAD(P)H + H+
3β-hydroxy-4β-methyl-5α-cholest-7-ene-4α-carboxylate + NAD(P)+ = 4α-methyl-5α-cholest-7-en-3-one + CO2 + NAD(P)H
a 3β-hydroxy-4α-carboxysteroid + NAD(P)+ = a 3-oxosteroid + CO2 + NAD(P)H

In Redox half-reactions:
NAD(P)+[in] + H+[in] + 2 e-[membrane]NAD(P)H[in]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: HMP-P synthase , UDP-galactopyranose mutase , flavin-dependent thymidylate synthase , flavin-dependent thymidylate synthase , (S)-2-hydroxypropylphosphonate epoxidase , GDP-D-mannose 4,6-dehydratase


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Fri May 22, 2015, BIOCYC14B.