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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 UTC
HMDB IDHMDB0059644
Secondary Accession Numbers
  • HMDB59644
Metabolite Identification
Common NameNADHX
DescriptionNADHX, also known as monohydroxytetrahydronicotinamide adenine dinucleotide, 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. NADHX is a very strong basic compound (based on its pKa). NADHX exists in all living organisms, ranging from bacteria to humans. Outside of the human body, NADHX has been detected, but not quantified in, several different foods, such as pineapples, fireweeds, silver lindens, mentha (mint), and broad beans. This could make NADHX a potential biomarker for the consumption of these foods. NADHX is a substrate for ATP-dependent NAD(P)H-hydrate dehydratase.
Structure
Data?1583342457
Synonyms
ValueSource
(6S)-6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotideChEBI
6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideChEBI
BETA-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotideChEBI
(6S)-6b-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotideGenerator
(6S)-6β-hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotideGenerator
6b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
6β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
b-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotideGenerator
β-6-hydroxy-1,4,5,6-tetrhydronicotinamide adenine dinucleotideGenerator
(S)-NADH-hydrateKEGG
(S)-NADHXKEGG
(6S)-6-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideKEGG
(S)-NADH-hydric acidGenerator
(6S)-6b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
(6S)-6Β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
(6S)-6-b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
(6S)-6-Β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotideGenerator
Monohydroxytetrahydronicotinamide adenine dinucleotideHMDB
NADHXHMDB
Chemical FormulaC21H31N7O15P2
Average Molecular Weight683.4563
Monoisotopic Molecular Weight683.135336381
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 Name(S)-nadhx
CAS Registry Number116561-22-9
SMILES
NC(=O)C1=CN([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)[C@@H](O)[C@H]2O)[C@@H](O)CC1
InChI Identifier
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
InChI KeyIDBZKGQRLBFUFQ-VPHRTNKSSA-N
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.26 g/LALOGPS
logP-1.9ALOGPS
logP-6.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area337.85 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity144.05 m³·mol⁻¹ChemAxon
Polarizability58.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-251.33730932474
DeepCCS[M+Na]+226.05230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NADHXNC(=O)C1=CN([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)[C@@H](O)[C@H]2O)[C@@H](O)CC15077.2Standard polar33892256
NADHXNC(=O)C1=CN([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)[C@@H](O)[C@H]2O)[C@@H](O)CC13717.7Standard non polar33892256
NADHXNC(=O)C1=CN([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)[C@@H](O)[C@H]2O)[C@@H](O)CC16046.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (Non-derivatized) - 70eV, Positivesplash10-017m-1211913000-25814eadfd52e71a50a22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADHX GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 10V, Positive-QTOFsplash10-000i-0920104000-1528abc2c0a942f490312015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 20V, Positive-QTOFsplash10-000i-0900000000-d2229364feb237809db12015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 40V, Positive-QTOFsplash10-000i-1900000000-c059fcd5287ebb9026622015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 10V, Negative-QTOFsplash10-001i-0900316000-b56bcca46a39880ba5312015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 20V, Negative-QTOFsplash10-001i-1900100000-fd7ebe873ef8a790e7102015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 40V, Negative-QTOFsplash10-0a7l-3900000000-e65fb28b52244d9bf64b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 10V, Positive-QTOFsplash10-00lu-0700009000-84c79a506933cd12dcfe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 20V, Positive-QTOFsplash10-00lr-0613159000-d52e45cdb114fde72b482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 40V, Positive-QTOFsplash10-000i-0922100000-1592b6a3cfff1659a1742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 10V, Negative-QTOFsplash10-03e9-0000009000-4a10771d72bd52ae30c52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 20V, Negative-QTOFsplash10-057i-6000069000-2683c91f3d01d3ae1e5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADHX 40V, Negative-QTOFsplash10-0bvi-6915704000-3bb96fcd514c7f9b7fa82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030173
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04856
BioCyc IDCPD-653
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440516
PDB IDNAX
ChEBI ID44236
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available