Record Information
Version1.0
Creation date2011-09-21 00:15:07 UTC
Update date2018-01-23 20:19:39 UTC
Primary IDFDB022511
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFAD
DescriptionFAD, also known as adeflavin or flamitajin b, belongs to the class of organic compounds 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. FAD is a strong basic compound (based on its pKa). FAD exists in all living species, ranging from bacteria to humans. FAD has been detected, but not quantified in, several different foods, such as shallots, mixed nuts, wild rices, common wheats, and romaine lettuces. This could make FAD a potential biomarker for the consumption of these foods.
CAS Number146-14-5
Structure
Thumb
Synonyms
SynonymSource
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavineChEBI
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]ChEBI
Flavin adenine dinucleotideChEBI
FLAVIN-adenine dinucleotideChEBI
Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosineChEBI
Riboflavin 5'-adenosine diphosphateChEBI
AdeflavinKegg
Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with riboflavineGenerator
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphoric acid]Generator
Riboflavin 5'-(trihydrogen diphosphoric acid), 5'-5'-ester with adenosineGenerator
Riboflavin 5'-adenosine diphosphoric acidGenerator
1H-Purin-6-amine flavin dinucleotideHMDB
1H-Purin-6-amine flavine dinucleotideHMDB
Adenine-flavin dinucleotideHMDB
Adenine-flavine dinucleotideHMDB
Adenine-riboflavin dinuceotideHMDB
Adenine-riboflavin dinucleotideHMDB
Adenine-riboflavine dinucleotideHMDB
Flamitajin bHMDB
Flanin FHMDB
Flavin adenine dinucleotide oxidizedHMDB
Flavine adenosine diphosphateHMDB
Flavine-adenine dinucleotideHMDB
FlavitanHMDB
FlazirenHMDB
Isoalloxazine-adenine dinucleotideHMDB
Riboflavin-adenine dinucleotideHMDB
Riboflavine-adenine dinucleotideHMDB
Dinucleotide, flavin-adenineHMDB
Adenosine 5'-(trihydrogen pyroate), 5'-5'-ester with riboflavineChEBI
Adenosine 5'-(trihydrogen pyroic acid), 5'-5'-ester with riboflavineGenerator
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diate]ChEBI
Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diic acid]Generator
FADhmdb
Flamitajin Bhmdb
flavin adenine dinucleotide oxidizedhmdb
Flavin-adenine dinucleotidehmdb
Flavine adenosine diateHMDB
Riboflavin 5'-(trihydrogen diate), 5'-5'-ester with adenosineChEBI
Riboflavin 5'-(trihydrogen diic acid), 5'-5'-ester with adenosineGenerator
Riboflavin 5'-adenosine diateChEBI
Riboflavin 5'-adenosine diic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.25 g/LALOGPS
logP-0.78ALOGPS
logP-4.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area356.42 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity177.43 m³·mol⁻¹ChemAxon
Polarizability70.53 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H33N9O15P2
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
InChI IdentifierInChI=1S/C27H33N9O15P2/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/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
InChI KeyVWWQXMAJTJZDQX-UYBVJOGSSA-N
Isomeric SMILESCC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
Average Molecular Weight785.5497
Monoisotopic Molecular Weight785.157134455
Classification
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassFlavin nucleotides
Sub ClassNot Available
Direct ParentFlavin nucleotides
Alternative Parents
Substituents
  • Flavin nucleotide
  • (3'->5')-dinucleotide
  • (3'->5')-dinucleotide or analogue
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Flavin
  • Isoalloxazine
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Diazanaphthalene
  • Pentose monosaccharide
  • Pteridine
  • 6-aminopurine
  • Quinoxaline
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Pyrazine
  • Tetrahydrofuran
  • Azole
  • Vinylogous amide
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Lactam
  • Polyol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0170-1032960400-cdd3286ebb1dea7c4f54JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0001200900-b0740b3d33d50996ccdeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000m-0105900000-3abff26d5bb35f8527b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0931700000-73f360589a13230eea7aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000j-0908600300-b1eccda8ebae8b9e4cc1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-bdb826f9c3cbc09eff9bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0019800000-00ad56b6b6a3bb4516e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000b-0009400000-667064ca470a5c341974JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000j-0509700500-8766cb874f927ed5a795JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-3125e04c09a14c62f22aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0019700000-78c46ea4b4f562757e56JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000b-0009400000-94b845d2c8d082b9484cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0000100900-6bac7b7f631dfc074a0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0920000000-49c9d4fb9b57a59f45a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0003900000-572f0b1bd59f71ab3c5fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0003900000-d2ede6a2e7183f1c32a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0000100900-78554afbc26abe26af35JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0930000000-274da0a01c651b791733JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0003900000-55939cda9e14fc582757JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0003900000-db784762434fac3d351fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0932110400-f05626487523221c34deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0930000000-86c3d6490bc3a27e053aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0980000000-58a46c839e0e520474d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-8482400900-2c4839849821d2807c57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-5920100000-b38889aa3d09576e2f3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-3900000000-f7144f6355fab252a516JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID559059
ChEMBL IDCHEMBL1232653
KEGG Compound IDC00016
Pubchem Compound ID643975
Pubchem Substance IDNot Available
ChEBI ID16238
Phenol-Explorer IDNot Available
DrugBank IDDB03147
HMDB IDHMDB01248
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33521
KNApSAcK IDNot Available
HET IDFAD
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFAD
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)DAKQ3LXA3
Putative uncharacterized protein DKFZp686B0215DKFZp686B0215Q5HYI4
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1NDUFB1O75438
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 12NDUFA12Q9UI09
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 1NDUFA1O15239
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4-like 2NDUFA4L2Q9NRX3
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 3NDUFA3O95167
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 8NDUFA8P51970
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4NDUFA4O00483
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 11NDUFA11Q86Y39
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 6NDUFA6P56556
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 4NDUFB4O95168
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 7NDUFA7O95182
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 2NDUFA2O43678
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 5, mitochondrialNDUFB5O43674
NADH dehydrogenase [ubiquinone] 1 subunit C2NDUFC2O95298
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 3NDUFB3O43676
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 7NDUFB7P17568
Acyl carrier protein, mitochondrialNDUFAB1O14561
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 5NDUFA5Q16718
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 9NDUFB9Q9Y6M9
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 13NDUFA13Q9P0J0
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 11, mitochondrialNDUFB11Q9NX14
NADH dehydrogenase (Ubiquinone) 1 beta subcomplex, 2, 8kDaNDUFB2A4D1T5
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
Glycerol Phosphate ShuttleSMP00124 Not Available
Riboflavin MetabolismSMP00070 map00740
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference