MiMeDB: Showing metabocard for NADPH (MMDBc0029795)

Microbial

Human

Plant

Animal

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:41:56 UTC

Update Date

2024-04-30 19:42:01 UTC

Metabolite ID

MMDBc0029795

Metabolite Identification

Common Name

NADPH

Description

Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₁H₃₀N₇O₁₇P₃

Average Mass

745.4209

Monoisotopic Mass

745.091102105

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

53-57-6

SMILES

Not Available

InChI Identifier

InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1

InChI Key

ACFIXJIJDZMPPO-NCHANQSKSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

All Tissues
Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank
(3α,5β,7β,23R)-3,7,23-Trihydroxycholanic acid secondary bile acid biosynthesis (hdh operon)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) metabolism
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) metabolism
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) metabolism
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) metabolism

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018037	Hydrogen Ion	NADP	3-oxoacyl-[acyl-carrier-protein] reductase FabG	Reduction	PathBank	31602464
MMDBr0018038	NADP	Hydrogen Ion	Enoyl-[acyl-carrier-protein] reductase [NADH] FabI	Reduction	PathBank	31602464
MMDBr0018042	Hydrogen Ion	NADP	Enoyl-[acyl-carrier-protein] reductase [NADH] FabI	Reduction	PathBank	31602464
MMDBr0018080	NADPH	5,10-Methylene-THF	Bifunctional protein FolD		PathBank	31602464
MMDBr0018242	Sulfite	Hydrogen sulfide	Sulfite reductase [NADPH] hemoprotein beta-component	Reduction	PathBank	31602464
MMDBr0018308	Malic acid	Pyruvic acid	NADP-dependent malic enzyme		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	66	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human saliva; River trout ; Cattle ; Rat ; Turkey ; Sheep ; Dog ; Lion ; Chicken ; American dog tick ; Human supragingival plaque; Human mucosa	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	506	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish ; Goat feces; Sheep feces	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	639	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human saliva; River trout ; Cattle ; Rat ; Turkey ; Sheep ; Dog ; Lion ; Chicken ; American dog tick ; Human supragingival plaque; Human mucosa	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	57	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	171	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	3	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	136	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	39	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish ; Goat feces; Sheep feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	15	Human feces; Human ; Pig	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	10	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	20	Human feces; Human ; Goat	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	143	Human feces; Human saliva; Human supragingival plaque	Unknown
Bacteria/Eubacteria	Chlamydiae	10	Human ; Sheep ; Cat
Eukaryota/Fungi	Mucoromycota	2
Bacteria/Eubacteria	Cyanobacteria	35	Human
Bacteria	nah	5
Archaea/Archaea	Crenarchaeota	23	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	43	Human feces; Human	Metabolic reconstruction
Archaea/Archaea	nah	10
Bacteria/Eubacteria	Acidobacteria	3
Bacteria/Eubacteria	Aquificae	4
Bacteria/Eubacteria	Chlorobi	11
Bacteria/Eubacteria	Chloroflexi	10
Bacteria/Eubacteria	Deinococcus-thermus	5
Bacteria/Eubacteria	Dictyoglomi	2
Bacteria/Eubacteria	Thermotogae	10
Bacteria	Tenericutes	2	Human feces; Human ; Goat	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	16	Human feces
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Elusimicrobia	2
Bacteria/Eubacteria	Nitrospirae	1
Viruses/Bamfordvirae	Nucleocytoviricota	2
Viruses/Heunggongvirae	Uroviricota	5
Eukaryota/Fungi	Microsporidia	1
Viruses/Heunggongvirae	Peploviricota	4
Eukaryota/Fungi	Chytridiomycota	2
Bacteria	Deinococcus-thermus	1
Archaea/Archaea	Korarchaeota	1
Bacteria	Cyanobacteria	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	51.0	34.0	81.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human All tissues	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Birkmayer GJ, Birkmayer W: Stimulation of endogenous L-dopa biosynthesis--a new principle for the therapy of Parkinson's disease. The clinical effect of nicotinamide adenine dinucleotide (NADH) and nicotinamide adenine dinucleotidephosphate (NADPH). Acta Neurol Scand Suppl. 1989;126:183-7. doi: 10.1111/j.1600-0404.1989.tb01800.x. [PubMed:2618590 ]
Afanas'ev IB, Suslova TB, Cheremisina ZP, Abramova NE, Korkina LG: Study of antioxidant properties of metal aspartates. Analyst. 1995 Mar;120(3):859-62. doi: 10.1039/an9952000859. [PubMed:7741242 ]
Shindo Y, Witt E, Han D, Epstein W, Packer L: Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol. 1994 Jan;102(1):122-4. doi: 10.1111/1523-1747.ep12371744. [PubMed:8288904 ]
Lee AJ, Zhu BT: NADPH-dependent formation of polar and nonpolar estrogen metabolites following incubations of 17 beta-estradiol with human liver microsomes. Drug Metab Dispos. 2004 Aug;32(8):876-83. doi: 10.1124/dmd.32.8.876. [PubMed:15258114 ]
Karanam BV, Hop CE, Liu DQ, Wallace M, Dean D, Satoh H, Komuro M, Awano K, Vincent SH: In vitro metabolism of MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl) phenyl]methyl]benzamide], a peroxisome proliferator-activated receptor alpha/gamma agonist. I. Role of cytochrome P450, methyltransferases, flavin monooxygenases, and esterases. Drug Metab Dispos. 2004 Sep;32(9):1015-22. doi: 10.1124/dmd.104.000034. [PubMed:15319344 ]
Conley AJ, Pattison JC, Bird IM: Variations in adrenal androgen production among (nonhuman) primates. Semin Reprod Med. 2004 Nov;22(4):311-26. doi: 10.1055/s-2004-861548. [PubMed:15635499 ]
Iwata H, Tezuka Y, Kadota S, Hiratsuka A, Watabe T: Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. Drug Metab Pharmacokinet. 2005 Feb;20(1):34-45. doi: 10.2133/dmpk.20.34. [PubMed:15770073 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Lin CC, Wong BK, Burgey CS, Gibson CR, Singh R: In vitro metabolism of a thrombin inhibitor and quantitation of metabolically generated cyanide. J Pharm Biomed Anal. 2005 Oct 4;39(5):1014-20. doi: 10.1016/j.jpba.2005.05.028. Epub 2005 Jul 14. [PubMed:16023819 ]
Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. doi: 10.1124/dmd.105.004010. Epub 2005 Sep 23. [PubMed:16183782 ]
Soglia JR, Contillo LG, Kalgutkar AS, Zhao S, Hop CE, Boyd JG, Cole MJ: A semiquantitative method for the determination of reactive metabolite conjugate levels in vitro utilizing liquid chromatography-tandem mass spectrometry and novel quaternary ammonium glutathione analogues. Chem Res Toxicol. 2006 Mar;19(3):480-90. doi: 10.1021/tx050303c. [PubMed:16544956 ]

Showing metabocard for NADPH (MMDBc0029795)

MOL for #<Metabolite:0x00007efbec298e40>

3D MOL for #<Metabolite:0x00007efbec298e40>

3D SDF for #<Metabolite:0x00007efbec298e40>

3D-SDF for #<Metabolite:0x00007efbec298e40>

PDB for #<Metabolite:0x00007efbec298e40>

3D PDB for #<Metabolite:0x00007efbec298e40>

SMILES for #<Metabolite:0x00007efbec298e40>

INCHI for #<Metabolite:0x00007efbec298e40>

Structure for #<Metabolite:0x00007efbec298e40>

3D Structure for #<Metabolite:0x00007efbec298e40>