P. aeruginosa Metabolome Database: NADPH (PAMDB110539)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB110539

Identification

Name:

NADPH

Description:

Tetraanion of NADPH arising from deprotonation of the diphosphate and phosphate OH groups; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

reduced nicotinamide adenine dinucleotide phosphate
NADPH2
NADPH₂
dihydrotriphosphopyridine nucleotide
reduced dihydrotriphosphopyridine nucleotide
dihydronicotinamide adenine dinucleotide phosphate
dihydronicotinamide adenine dinucleotide phosphate reduced
reduced NADP
NADP-red
TPNH
dihydronicotinamide adenine dinucleotide-P
β-NADPH

Chemical Formula:

C₂₁H₂₆N₇O₁₇P₃

Average Molecular Weight:

741.39

Monoisotopic Molecular Weight:

745.0911021051

InChI Key:

ACFIXJIJDZMPPO-NNYOXOHSSA-J

InChI:

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)/p-4/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

CAS number:

53-57-6

IUPAC Name:

2'-O-phosphonatoadenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] diphosphate}

Traditional IUPAC Name:

[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid

SMILES:

C5(N(C1(OC(C(C1O)O)COP(OP(OCC4(C(C(C(N3(C2(=C(C(=NC=N2)N)N=C3)))O4)OP([O-])([O-])=O)O))([O-])=O)(=O)[O-]))C=C(CC=5)C(=O)N)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Nucleosides, nucleotides, and analogues

Sub Class

(5'->5')-dinucleotides

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside 2',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
N-substituted nicotinamide
Organic pyrophosphate
6-aminopurine
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Dihydropyridine
Monosaccharide
N-substituted imidazole
Imidolactam
Organic phosphoric acid derivative
Alkyl phosphate
Hydropyridine
Phosphoric acid ester
Pyrimidine
Primary aromatic amine
Oxolane
Heteroaromatic compound
Imidazole
Vinylogous amide
Azole
Secondary alcohol
Amino acid or derivatives
Primary carboxylic acid amide
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Enamine
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Carbonyl group
Organic oxide
Primary amine
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.45 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-7.5	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	4.92	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	364.15 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	153.87 m³·mol^-1	ChemAxon
Polarizability	60.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

More...

Pathways:

Androgen and Estrogen Metabolism pae00150
Arachidonic Acid Metabolism pae00590
Arginine and Proline Metabolism pae00330
Beta-Alanine Metabolism pae00410
Bile Acid Biosynthesis pae00120
Fatty Acid Elongation In Mitochondria pae00062
Folate Metabolism pae00670
Fructose and Mannose Degradation pae00051
Glutamate Metabolism pae00250
Glutathione Metabolism pae00480
Glycerolipid Metabolism pae00561
Histidine Metabolism pae00340
Lysine Degradation pae00310
Nicotinate and Nicotinamide Metabolism pae00760
Pentose Phosphate Pathway pae00030
Pterine Biosynthesis pae00790
Purine Metabolism pae00230
Pyrimidine Metabolism pae00240
Pyruvate Metabolism pae00620
Retinol Metabolism pae00830
Sphingolipid Metabolism pae00500
Steroid Biosynthesis pae00100
Steroidogenesis pae00140
Tryptophan Metabolism pae00380
Tyrosine Metabolism pae00350
Ubiquinone Biosynthesis pae00130

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-02tj-1838493720-b38b37650e8976905bb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0550-2694875730-0dc522520957880672cb	View in MoNA
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available

References

References:

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(1):18. [15882454 ]
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. [8288904 ]
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. [15770073 ]
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. [2618590 ]
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. [15258114 ]
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. Epub 2005 Sep 23. [16183782 ]
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-trifluoromet hyl) 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. [15319344 ]
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. [16544956 ]
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. [7741242 ]
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. Epub 2005 Jul 14. [16023819 ]
Conley AJ, Pattison JC, Bird IM: Variations in adrenal androgen production among (nonhuman) primates. Semin Reprod Med. 2004 Nov;22(4):311-26. [15635499 ]

Synthesis Reference:

Seelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Letters (1996), 37(9), 1377-80.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CAS	2646-71-1
ChEBI	57783
ChemSpider	10239199
HMDB	HMDB00221
IAF1260	33486
KEGG	C00005
MetaboLights	MTBLC57783
PubChem	15983949

NADPH (PAMDB110539)

Structure for NADPH (PAMDB110539)