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FAD (PC000289)

Record Information
Version1.0
Creation date2015-10-09 22:29:41 UTC
Update date2017-01-19 02:36:19 UTC
FoodComEx IDPC000289
FoodDB RecordFDB022511
Chemical Information
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 drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is a strong basic compound (based on its pKa). FAD exists in all living species, ranging from bacteria to humans. In humans, FAD is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, FAD has been detected, but not quantified in, several different foods, such as other bread, passion fruits, asparagus, kelps, and green bell peppers. This could make FAD a potential biomarker for the consumption of these foods. A FAD in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.
CAS Number146-14-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
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
Flanin Fhmdb
Flavin adenine dinucleotidehmdb
flavin adenine dinucleotide oxidizedhmdb
Flavin-adenine dinucleotidehmdb
Flavine adenosine diateHMDB
Flavine adenosine diphosphatehmdb
Flavine-adenine dinucleotidehmdb
Flavitanhmdb
Flazirenhmdb
Isoalloxazine-adenine dinucleotidehmdb
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
Riboflavin 5'-adenosine diphosphatehmdb
Riboflavin-adenine dinucleotidehmdb
Riboflavine-adenine dinucleotidehmdb
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci M453