NADPH (BioCAD00000014977)
Metabolite Card
Formula: C21H30N7O17P3 (745.0911)
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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
Synonyms [en]
NADPH; Reduced Nicotinamide Adenine Dinucleotide Phosphate; TPNH; reduced nicotinamide-adenine dinucleotide phosphate; Dihydronicotinamide-adenine dinucleotide phosphate; Reduced triphosphopyridine nucleotide
Last reviewed on 2024-06-28.
Cite this Page
NADPH. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000014977). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
NADPH is the reduced form of NADP+, and NADP+ is the oxidized form of NADPH. Nicotinamide adenine dinucleotide phosphate (NADP) is a coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled with a pyrophosphate linkage to 5'-phosphate adenosine 2',5'-bisphosphate. NADP serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). NADP is formed through the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage (Dorland, 27th ed). This extra phosphate is added by the enzyme NAD+ kinase and removed via NADP+ phosphatase. NADP is also known as TPN (triphosphopyridine nucleotide) and it is an important cofactor used in anabolic reactions in all forms of cellular life. Examples include the Calvin cycle, cholesterol synthesis, fatty acid elongation, and nucleic acid synthesis (Wikipedia).
DBLinks
- CAS Registry Number: 2646-71-1
- PubChem CID: 5884
- ChEBI: 16474
- HMDB: HMDB0000221
- LipidMaps:
- KEGG: C00005
- BioCyc:
- NCBI MeSH: NADP
- Wikipedia: Nicotinamide adenine dinucleotide phosphate
Other DBLinks
- CAS Registry Number: 2646-71-1
- CAS Registry Number: 53-57-6
- PubChem: 5884
- ChEBI: ChEBI:16474
- HMDB: HMDB0000221
- KEGG: C00005
- NCBI MeSH: NADP
- Wikipedia: Nicotinamide adenine dinucleotide phosphate
- DrugBank: DB02338
- RefMet: RM0157850
- MoNA: CCMSLIB00005721035
- MoNA: EMBL_MCF_2_0_HRMS_Library000276
- MoNA: HMDB0000221_ms_ms_361
- MoNA: HMDB0000221_ms_ms_362
- MoNA: HMDB0000221_ms_ms_363
- Metlin: METLIN_3691
- Coconut NaturalProduct: CNP0265401.1
- Coconut NaturalProduct: CNP0265401.2
- Coconut NaturalProduct: CNP0265401.3
- Coconut NaturalProduct: CNP0265401.5
Class / Ontology
- WishartLab ClassyFire: [(5'->5')-dinucleotides] (5'->5')-dinucleotides
- RefMet: [Nicotinamide dinucleotides] Nicotinamide dinucleotides
- ChEBI: [CHEBI:16474] NADPH
- Coconut NaturalProduct: [Purine nucleos(t)ides] Purine nucleos(t)ides
| ID | EC Number | Name |
|---|---|---|
| KEGG:R00105 | 2.7.1.86 | ATP:NADH 2'-phosphotransferase |
| KEGG:R00106 | 1.6.2.4 | NADPH:ferricytochrome oxidoreductase |
| KEGG:R00108 | 1.6.2.5 | NADPH:ferricytochrome-c2 oxidoreductase |
| KEGG:R00109 | 1.6.2.6 | NADPH:ferrileghemoglobin oxidoreductase |
| KEGG:R00111 | 1.14.13.39 | N-(omega)-hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming) |
| KEGG:R00112 | 1.6.1.1 | NADPH:NAD+ oxidoreductase |
| KEGG:R00113 | 1.11.1.2 | NADPH:hydrogen-peroxide oxidoreductase |
| KEGG:R00114 | 1.4.1.13 | L-glutamate:NADP+ oxidoreductase (transaminating) |
| KEGG:R00115 | 1.8.1.7 | glutathione:NADP+ oxidoreductase |
| KEGG:R00134 | 1.17.1.10 | formate:NADP+ oxidoreductase |
| KEGG:R00146 | 1.4.1.1 | alpha-amino acid:NADP+ oxidoreductase (deaminating) |
| KEGG:R00205 | 1.2.1.49 | 2-oxopropanal:NADP+ oxidoreductase |
| KEGG:R00210 | 1.2.1.51 | pyruvate:NADP+ 2-oxidoreductase (CoA-acetylating) |
| KEGG:R00216 | 1.1.1.40 | (S)-malate:NADP+ oxidoreductase(oxaloacetate-decarboxylating) |
| KEGG:R00248 | 1.4.1.3 | L-glutamate:NADP+ oxidoreductase (deaminating) |
| KEGG:R00264 | 1.2.1.3 | 2,5-dioxopentanoate:NADP+ 5-oxidoreductase |
| KEGG:R00265 | 1.2.1.52 | 2-oxoglutarate:NADP+ 2-oxidoreductase (CoA-succinylating) |
| KEGG:R00267 | 1.1.1.42 | isocitrate:NADP+ oxidoreductase (decarboxylating) |
| KEGG:R00282 | 1.6.99.1 | NADPH:acceptor oxidoreductase |
| KEGG:R00301 | 1.1.1.119 | D-glucose:NADP+ 1-oxidoreductase |
Taxonomy Source
- Escherichia coli [ncbi taxid: 562]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Escherichia coli [ncbi taxid: 562]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:LEISH_PWY3IU-99 | superpathway of central carbon metabolism |
| BioCyc:LEISH_TCA | TCA cycle |
| BioCyc:LEISH_GLUCONEO-PWY | gluconeogenesis I |
| BioCyc:LEISH_PWY3IU-235 | folate metabolism |
| BioCyc:LEISH_PWY3IU-1025 | trypanothione redox reactions |
| BioCyc:LEISH_SPHINGOLIPID-SYN-PWY | sphingolipid metabolism |
| BioCyc:LEISH_PWY-5080 | very long chain fatty acid biosynthesis |
| BioCyc:LEISH_PWY3IU-39 | oxaloacetate degradation to pyruvate |
| BioCyc:LEISH_PWY-5651 | tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde |
| BioCyc:TRYPANO_PWY-5651 | tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde |
| BioCyc:TRYPANO_ANARESP1-PWY | respiration (anaerobic) |
| BioCyc:TRYPANO_GLYCOLYSIS-TCA-GLYOX-BYPASS | superpathway of glycolysis, pyruvate dehydrogenase, TCA, and glyoxylate bypass |
| BioCyc:TRYPANO_PWY0-781 | aspartate superpathway |
| BioCyc:TRYPANO_PWY-724 | superpathway of lysine, threonine and methionine biosynthesis II |
| BioCyc:TRYPANO_PWY-3001 | isoleucine biosynthesis I |
| BioCyc:TRYPANO_PWY-922 | mevalonate pathway I |
| BioCyc:TRYPANO_PWY-3841 | formylTHF biosynthesis II |
| BioCyc:TRYPANO_RIBOSYN2-PWY | flavin biosynthesis I (bacteria and plants) |
| BioCyc:TRYPANO_PWY-4081 | glutathione redox reactions I |
| BioCyc:TRYPANO_ILEUSYN-PWY | isoleucine biosynthesis I (from threonine) |