P. aeruginosa Metabolome Database: NADPH (PAMDB000615)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000615

Identification

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 View Structure

Synonyms:

2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-delta-ribofuranosylnicotinamide
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-δ-ribofuranosylnicotinamide
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-β-δ-ribofuranosylnicotinamide
2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-delta-ribofuranosylnicotinamide
2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-δ-ribofuranosylnicotinamide
2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-β-δ-ribofuranosylnicotinamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-delta-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-δ-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-β-δ-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-delta-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-δ-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-β-δ-ribofuranosyl-3-pyridinecarboxamide
B-NADPH
b-Nicotinamide-adenine-dinucleotide-phosphate
B-Nicotinamide-adenine-dinucleotide-phosphorate
B-Nicotinamide-adenine-dinucleotide-phosphoric acid
Beta-NADPH
beta-Nicotinamide-adenine-dinucleotide-phosphate
Beta-Nicotinamide-adenine-dinucleotide-phosphorate
Beta-Nicotinamide-adenine-dinucleotide-phosphoric acid
Dihydrocodehydrogenase
Dihydrocodehydrogenase II
Dihydronicotinamide adenine dinucleotide phosphate
Dihydronicotinamide adenine dinucleotide phosphate reduced
Dihydronicotinamide adenine dinucleotide phosphoric acid
Dihydronicotinamide adenine dinucleotide phosphoric acid reduced
Dihydronicotinamide adenine dinucleotide-P
Dihydrotriphosphopyridine nucleotide
Dihydrotriphosphopyridine nucleotide reduced
NADP(H)
NADP-red
NADP-reduced
NADPH
NADPH+H+
NADPH2
NADPH₂
NADPH⁺H⁺
Nicotinamide adenine dinucleotide phosphate - reduced
Nicotinamide adenine dinucleotide phosphoric acid - reduced
Nicotinamide-adenine-dinucleotide-phosphate
Nicotinamide-adenine-dinucleotide-phosphorate
Nicotinamide-adenine-dinucleotide-phosphoric acid
Reduced Codehydrase
Reduced Codehydrase II
Reduced Coenzyme
Reduced Coenzyme II
Reduced Cozymase
Reduced Cozymase II
Reduced triphosphopyridine nucleotide
TPNH
Triphosphopyridine nucleotide reduced
β-NADPH
β-Nicotinamide-adenine-dinucleotide-phosphate
β-Nicotinamide-adenine-dinucleotide-phosphorate
β-Nicotinamide-adenine-dinucleotide-phosphoric acid

Chemical Formula:

C₂₁H₃₀N₇O₁₇P₃

Average Molecular Weight:

745.4209

Monoisotopic Molecular Weight:

745.091102105

InChI Key:

ACFIXJIJDZMPPO-NCHANQSKSA-N

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)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1

CAS number:

53-57-6

IUPAC Name:

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

Traditional IUPAC Name:

nadph

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=C(N)N=CN=C23)[C@H](O)[C@@H]1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 2',5'-bisphosphate
Nicotinamide-nucleotide
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
N-substituted nicotinamide
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Dihydropyridinecarboxylic acid derivative
Monoalkyl phosphate
Dihydropyridine
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Hydropyridine
Heteroaromatic compound
Oxolane
Imidazole
Azole
Tertiary amine
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Enamine
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NADP (CHEBI:16474 )
NAD(P)H (CHEBI:16474 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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	63.54 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:

Cytoplasm

Reactions:

More...

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Amino sugar and nucleotide sugar metabolism pae00520
Arginine and proline metabolism pae00330
Ascorbate and aldarate metabolism pae00053
Benzoate degradation via CoA ligation pae00632
Benzoate degradation via hydroxylation pae00362
Biosynthesis of unsaturated fatty acids pae01040
Biotin metabolism pae00780
Butanoate metabolism pae00650
Butirosin and neomycin biosynthesis pae00524
Caprolactam degradation pae00930
Carbon fixation in photosynthetic organisms pae00710
Citrate cycle (TCA cycle) pae00020
Cysteine and methionine metabolism pae00270
Fatty acid biosynthesis pae00061
Fatty acid metabolism pae00071
Folate biosynthesis pae00790
Fructose and mannose metabolism pae00051
Glutathione metabolism pae00480
Glycerolipid metabolism pae00561
Glycerophospholipid metabolism pae00564
Glycine, serine and threonine metabolism pae00260
Glycolysis / Gluconeogenesis pae00010
Glyoxylate and dicarboxylate metabolism pae00630
Lysine biosynthesis pae00300
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Monobactam biosynthesis pae00261
Nicotinate and nicotinamide metabolism pae00760
Nitrogen metabolism pae00910
One carbon pool by folate pae00670
Pantothenate and CoA biosynthesis pae00770
Pentose and glucuronate interconversions pae00040
Pentose phosphate pathway pae00030
Peptidoglycan biosynthesis pae00550
Phenylalanine metabolism pae00360
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Photosynthesis pae00195
Polyketide sugar unit biosynthesis pae00523
Porphyrin and chlorophyll metabolism pae00860
Purine metabolism pae00230
Pyrimidine metabolism pae00240
Pyruvate metabolism pae00620
Reductive carboxylate cycle (CO2 fixation) pae00720
Riboflavin metabolism pae00740
Selenoamino acid metabolism pae00450
Starch and sucrose metabolism pae00500
Streptomycin biosynthesis pae00521
Sulfur metabolism pae00920
Terpenoid backbone biosynthesis pae00900
Thiamine metabolism pae00730
Trinitrotoluene degradation pae00633
Tyrosine metabolism pae00350
Ubiquinone and other terpenoid-quinone biosynthesis pae00130
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0921103300-a94dc77e4683c53f1e1c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-5fcc7bc2ff00254e837a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0920000000-91a94a0d16f7db6907e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0036-6900111800-7f73a4ecf431645a13cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3901000000-b9bf964190caf0afebde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900000000-f6e201cd60ed9314f31a	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

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 (1

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16474
HMDB ID	HMDB00221
Pubchem Compound ID	5884
Kegg ID	C00005
ChemSpider ID	17215925
Wikipedia	NADPH
BioCyc ID	NADPH
EcoCyc ID	NADPH
Ligand Expo	NDP

NADPH (PAMDB000615)

Structure for NADPH (PAMDB000615)