FADH2 (PAMDB110704)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110704
Identification
Name: FADH2
Description:The organophosphate oxoanion obtained by deprotonation of the diphosphate hydroxy groups of the reduced form of flavin adenine dinucleotide (FADH2).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • flavin adenine dinucleotide reduced
  • 1,5-dihydro-FAD
Chemical Formula: C27H33N9O15P2
Average Molecular Weight: 785.56
Monoisotopic Molecular Weight: 787.1727845218
InChI Key: YPZRHBJKEMOYQH-UYBVJOGSSA-L
InChI: InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/p-2/t14-,15+,16+,19-,20+,21+,26+/m0/s1
CAS number: 1910-41-4
IUPAC Name:adenosine 5'-(3-{D-ribo-5-[7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl]-2,3,4-trihydroxypentyl} diphosphate)
Traditional IUPAC Name: fadh(.)
SMILES:CC1(=C(C)C=C2(N(C3(NC(NC(=O)C(NC(=C1)2)=3)=O))CC(O)C(O)C(O)COP(OP([O-])(OCC6(C(O)C(O)C(N5(C=NC4(C(N)=NC=NC=45)))O6))=O)([O-])=O))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassFlavin nucleotides
Direct Parent Flavin nucleotides
Alternative Parents
Substituents
  • Flavin nucleotide
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Flavin
  • Pentose-5-phosphate
  • Pentose phosphate
  • Alkyldiarylamine
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pteridine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidone
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Benzenoid
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Pyrimidine
  • Vinylogous amide
  • Oxolane
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Urea
  • Lactam
  • Secondary amine
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen 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 Solubility2.65 mg/mLALOGPS
logP-0.93ALOGPS
logP-5.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area355.76 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity188.8 m3·mol-1ChemAxon
Polarizability72.42 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
D-gluconate + FAD + Hydrogen ion → 2-keto-D-gluconate + FADH2
isovaleryl-CoA + FAD + Hydrogen ion → 3-methylcrotonyl-CoA + FADH2
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0001200900-b0740b3d33d50996ccdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000m-0105900000-3abff26d5bb35f8527b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0931700000-73f360589a13230eea7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Zeller HD, Hille R, Jorns MS: Bacterial sarcosine oxidase: identification of novel substrates and a biradical reaction intermediate. Biochemistry. 1989 Jun 13;28(12):5145-54. [2475174 ]
  • Ramsey AJ, Alderfer JL, Jorns MS: Energy transduction during catalysis by Escherichia coli DNA photolyase. Biochemistry. 1992 Aug 11;31(31):7134-42. [1643047 ]
  • Ramsey AJ, Jorns MS: Effect of 5-deazaflavin on energy transduction during catalysis by Escherichia coli DNA photolyase. Biochemistry. 1992 Sep 15;31(36):8437-41. [1390627 ]
  • Jorns MS: DNA photorepair: chromophore composition and function in two classes of DNA photolyases. Biofactors. 1990 Oct;2(4):207-11. [2282137 ]
Synthesis Reference: Kavakli I Halil; Sancar Aziz Analysis of the role of intraprotein electron transfer in photoreactivation by DNA photolyase in vivo. Biochemistry (2004), 43(48), 15103-10.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS1910-41-4
ChEBI58307
HMDBHMDB01197
IAF1260132077
KEGGC01352
MetaboLightsMTBLC58307
PubChem25244872
Wikipediahttp://en.wikipedia.org/wiki/Flavin_adenine_dinucleotide