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Record Information
Version	2.0
Creation Date	2012-10-10 12:20:18 -0600
Update Date	2015-06-03 17:26:04 -0600
Secondary Accession Numbers	ECMDB23170
Identification
Name:	(6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide
Description	(6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide is a substrate for the enzymes ATP-dependent NAD(P)H-hydrate dehydratase which catalyzes the reaction ATP + (6S)-6beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide = ADP + phosphate + NADH. This is an intermediate in NADH "repair".
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x31f059c> Close
Synonyms:	(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (2R,3S,4R,5R)-5-(2S)-5-carbamoyl-2-hydroxy-3,4-dihydro-2H-pyridin-1-yl-3,4-dihydroxyoxolan-2-ylmethyl hydrogen phosphate (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (2R,3S,4R,5R)-5-(2S)-5-carbamoyl-2-hydroxy-3,4-dihydro-2H-pyridin-1-yl-3,4-dihydroxyoxolan-2-ylmethyl hydrogen phosphoric acid (6S)-6-b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide (6S)-6-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide (6S)-6-β-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide (6S)-6b-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide (6S)-6beta-hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide (6S)-6β-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide (S)-NADHX 6b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide 6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide 6β-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide b-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotide BETA-6-HYDROXY-1,4,5,6-TETRHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE β-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotide
Chemical Formula:	C21H31N7O15P2
Weight:	Average: 683.4563 Monoisotopic: 683.135336381
InChI Key:	IDBZKGQRLBFUFQ-VPHRTNKSSA-N
InChI:	InChI=1S/C21H31N7O15P2/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(33)14(31)10(42-21)5-40-45(37,38)43-44(35,36)39-4-9-13(30)15(32)20(41-9)27-3-8(18(23)34)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-33H,1-2,4-5H2,(H2,23,34)(H,35,36)(H,37,38)(H2,22,24,25)/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1
CAS number:	Not Available
IUPAC Name:	[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-[(2S)-5-carbamoyl-2-hydroxy-1,2,3,4-tetrahydropyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Name:	(S)-nadhx
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=C(CC[C@]3([H])O)C(O)=N)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	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	Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Nicotinamide nucleotides Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Tetrahydropyridines Monoalkyl phosphates Imidolactams N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Vinylogous amides Secondary alcohols Primary carboxylic acid amides Amino acids and derivatives Oxacyclic compounds Alkanolamines Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines
Substituents	Purine nucleotide sugar Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Nicotinamide-nucleotide Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Imidazopyrimidine Purine Aminopyrimidine Monoalkyl phosphate Tetrahydropyridine Imidolactam Alkyl phosphate Hydropyridine Pyrimidine Monosaccharide N-substituted imidazole Organic phosphoric acid derivative Phosphoric acid ester Azole Vinylogous amide Tetrahydrofuran Imidazole Heteroaromatic compound Primary carboxylic acid amide Carboxamide group Secondary alcohol Amino acid or derivatives Organoheterocyclic compound Oxacycle Carboxylic acid derivative Azacycle Alkanolamine Organonitrogen compound Organooxygen compound Organic nitrogen compound Carbonyl group Organic oxygen compound Organopnictogen compound Alcohol Primary amine Amine Organic oxide Hydrocarbon derivative Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	hemiaminal (CHEBI:44236 ) tetrahydronicotinamide adenine dinucleotide (CHEBI:44236 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 6.26 g/L ALOGPS logP -1.9 ALOGPS logP -6.5 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.85 ChemAxon pKa (Strongest Basic) 4.01 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 337.85 Ų ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 144.05 m³·mol⁻¹ ChemAxon Polarizability 58.68 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:	ADP + (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide > Adenosine monophosphate + Inorganic phosphate + NADH ADP + (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide + (6S)-6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide phosphate <> Adenosine monophosphate + Phosphate + NADH + NADPH
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-017m-1211913000-25814eadfd52e71a50a2 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0920104000-1528abc2c0a942f49031 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900000000-d2229364feb237809db1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1900000000-c059fcd5287ebb902662 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-0900316000-b56bcca46a39880ba531 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-1900100000-fd7ebe873ef8a790e710 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a7l-3900000000-e65fb28b52244d9bf64b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00lu-0700009000-84c79a506933cd12dcfe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00lr-0613159000-d52e45cdb114fde72b48 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-0922100000-1592b6a3cfff1659a174 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03e9-0000009000-4a10771d72bd52ae30c5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-057i-6000069000-2683c91f3d01d3ae1e5c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0bvi-6915704000-3bb96fcd514c7f9b7fa8 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 44236 HMDB ID HMDB0059644 Pubchem Compound ID 440516 Kegg ID C04856 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available Ligand Expo NAX

Enzymes