Showing Compound NADPH (FDB021909)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:59 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021909

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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.) [HMDB]. NADPH is found in many foods, some of which are american pokeweed, rice, ginseng, and ostrich fern.

CAS Number

53-57-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide	HMDB
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide	HMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide	HMDB
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide	hmdb
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide	HMDB
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide	hmdb
Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide	HMDB
Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide	HMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide	HMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide	hmdb

Showing 1 to 10 of 49 entries

Predicted Properties

Property	Value	Source
Water Solubility	5.45 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-6.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	4	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	63.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C21H30N7O17P3

IUPAC name

{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-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

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

Isomeric 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

Average Molecular Weight

745.4209

Monoisotopic Molecular Weight

745.091102105

Classification

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

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
6-aminopurine
N-substituted nicotinamide
Organic pyrophosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Dihydropyridine
Aminopyrimidine
Organic phosphoric acid derivative
Pyrimidine
N-substituted imidazole
Hydropyridine
Alkyl phosphate
Phosphoric acid ester
Imidolactam
Monosaccharide
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Azole
Imidazole
Amino acid or derivatives
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
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

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

All tissues

Subcellular:

Biofluid and excreta:

Blood

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	NADPH, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-9421780200-89062ec4778392672634	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-02tj-1838493720-b38b37650e8976905bb0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0550-2694875730-0dc522520957880672cb	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0921104300-c1952197674952109d2c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-31adeef6c90e9070dfa4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0920000000-e29dcab04f59f9c7189c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0036-6900111800-ab3c73d03c4430e1b644	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-4901100000-96b551ade48c419935ed	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900000000-0898019fd8b891d5245e	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum

External Links

ChemSpider ID

17215925

ChEMBL ID

Not Available

KEGG Compound ID

C00005

Pubchem Compound ID

22833512

Pubchem Substance ID

Not Available

ChEBI ID

16474

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00221

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

33486

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

NADPH

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
2,4-dienoyl-CoA reductase, mitochondrial	DECR1	Q16698
3-hydroxy-3-methylglutaryl-coenzyme A reductase	HMGCR	P04035
3-ketodihydrosphingosine reductase	KDSR	Q06136
3-oxo-5-alpha-steroid 4-dehydrogenase 1	SRD5A1	P18405
3-oxo-5-alpha-steroid 4-dehydrogenase 2	SRD5A2	P31213
3-oxo-5-beta-steroid 4-dehydrogenase	AKR1D1	P51857
6-phosphogluconate dehydrogenase, decarboxylating	PGD	P52209
7-dehydrocholesterol reductase	DHCR7	Q9UBM7
Acyl-CoA synthetase family member 4	AASDH	Q4L235
Aflatoxin B1 aldehyde reductase member 2	AKR7A2	O43488

Showing 1 to 10 of 59 entries

Pathways

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Name	SMPDB Link	KEGG Link
Arachidonic Acid Metabolism	SMP00075	map00590
Ethanol Degradation	SMP00449	Not Available
Folate Metabolism	SMP00053	map00670
Glucose-Alanine Cycle	SMP00127	Not Available
Glutathione Metabolism	SMP00015	map00480
Glycerolipid Metabolism	SMP00039	map00561
Histidine Metabolism	SMP00044	map00340
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Plasmalogen Synthesis	SMP00479	Not Available
Pterine Biosynthesis	SMP00005	map00790