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Record Information
Version	2.0
Creation Date	2012-08-03 15:09:32 -0600
Update Date	2015-06-03 17:21:26 -0600
Secondary Accession Numbers	ECMDB21410
Identification
Name:	Nicotinamide hypoxanthine dinucleotide
Description	Nicotinamide hypoxanthine dinucleotide is a member of the chemical class known as Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa948ece4> Close
Synonyms:	Codehydrogenase I, deamino hydroxy analog Deamino DPN Deamino nicotinamide adenine dinucleotide Deamino-NAD Deaminocozymase Deaminodiphosphopyridine nucleotide Desamino-DPN Desamino-Nicotinamide-adenine dinucleotide Hypoxanthine-nicotinamide dinucleotide (VAN) NHD Nicotinamide-hypoxanthine dinucleotide (VAN)
Chemical Formula:	C21H27N6O15P2
Weight:	Average: 665.4178 Monoisotopic: 665.100962248
InChI Key:	DGVSIBCCYUVRNA-UHFFFAOYSA-O
InChI:	InChI=1S/C21H26N6O15P2/c22-17(32)9-2-1-3-26(4-9)20-15(30)13(28)10(40-20)5-38-43(34,35)42-44(36,37)39-6-11-14(29)16(31)21(41-11)27-8-25-12-18(27)23-7-24-19(12)33/h1-4,7-8,10-11,13-16,20-21,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)/p+1
CAS number:	1851-07-6
IUPAC Name:	1-{5-[({[({[3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-3-(C-hydroxycarbonimidoyl)-1λ⁵-pyridin-1-ylium
Traditional IUPAC Name:	1-(5-{[({[3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-3-(C-hydroxycarbonimidoyl)-1λ⁵-pyridin-1-ylium
SMILES:	OC1C(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)[N+]2=CC=CC(=C2)C(O)=N)OC(C1O)N1C=NC2=C1N=CN=C2O
Chemical Taxonomy
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	Purine nucleotide sugars Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Nicotinamide nucleotides Pentose phosphates Glycosylamines 6-oxopurines Hypoxanthines Monosaccharide phosphates Organic pyrophosphates Nicotinamides Pyrimidones Monoalkyl phosphates Pyridinium derivatives N-substituted imidazoles Heteroaromatic compounds Tetrahydrofurans Vinylogous amides Primary carboxylic acid amides Secondary alcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organic cations
Substituents	(5'->5')-dinucleotide Purine nucleotide sugar Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Nicotinamide-nucleotide Pyridine nucleotide Pentose-5-phosphate Pentose phosphate N-glycosyl compound Glycosyl compound Organic pyrophosphate 6-oxopurine Hypoxanthine Monosaccharide phosphate Pyridine carboxylic acid or derivatives Imidazopyrimidine Purine Nicotinamide Monoalkyl phosphate Pyrimidone Monosaccharide N-substituted imidazole Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Pyrimidine Pyridinium Pyridine Tetrahydrofuran Vinylogous amide Azole Imidazole Heteroaromatic compound Secondary alcohol Carboxamide group Primary carboxylic acid amide Organoheterocyclic compound Carboxylic acid derivative Oxacycle Azacycle Alcohol Organic nitrogen compound Hydrocarbon derivative Organonitrogen compound Organic oxide Organooxygen compound Organic oxygen compound Organopnictogen compound Organic cation Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 4.13 g/L ALOGPS logP -1.1 ALOGPS logP -10 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.86 ChemAxon pKa (Strongest Basic) 6.38 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 313.46 Ų ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 150.21 m³·mol⁻¹ ChemAxon Polarizability 57.68 ų 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:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 146± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0000009000-d8e02da56bcf122dbf7b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-0000009000-0fb3e89f513654a0630f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052g-7920202000-118ac68b1462e86cfeaf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-0000009000-bc382e77c9ea3f42024f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03xr-1100109000-9ac7fdd971dc1e342050 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-01rt-9300000000-100776e21c778772c23b View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 440334 Kegg ID C04423 ChemSpider ID 4326 Wikipedia ID Not Available BioCyc ID Not Available