(S)-NADHX (PAMDB110706)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110706
Identification
Name: (S)-NADHX
Description:A doubly-charged nucleotide-sugar oxoanion obtained by deprotonation of the diphosphate OH groups of (S)-NADHX; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (6S)-6-β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide
Chemical Formula: C21H29N7O15P2
Average Molecular Weight: 683.135336383
Monoisotopic Molecular Weight: 683.135336383
InChI Key: IDBZKGQRLBFUFQ-VPHRTNKSSA-L
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)/p-2/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1
CAS number: Not Available
IUPAC Name:(6S)-1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carboximidic acid
Traditional IUPAC Name: (6S)-1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-5,6-dihydro-4H-pyridine-3-carboximidic acid
SMILES:C1(=C(CCC(O)N1C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5))C(N)=O)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine 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
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Tetrahydropyridine
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Imidolactam
  • N-substituted imidazole
  • Hydropyridine
  • Primary aromatic amine
  • Monosaccharide
  • Phosphoric acid ester
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Amino acid or derivatives
  • Primary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Alkanolamine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.26 mg/mLALOGPS
logP-1.9ALOGPS
logP-7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area338.84 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity154.98 m3·mol-1ChemAxon
Polarizability60.17 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920104000-1528abc2c0a942f49031View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d2229364feb237809db1View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-c059fcd5287ebb902662View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900316000-b56bcca46a39880ba531View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900100000-fd7ebe873ef8a790e710View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-3900000000-e65fb28b52244d9bf64bView in MoNA
    References
    References:
    • Marbaix AY, Noël G, Detroux AM, Vertommen D, Van Schaftingen E, Linster CL (2011)Extremely conserved ATP- or ADP-dependent enzymatic system for nicotinamide nucleotide repair. The Journal of biological chemistry 286, Pubmed: 21994945
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI64074
    HMDBHMDB59644
    KEGGC04856
    PubChem25203523