Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:10 UTC
HMDB IDHMDB01248
Secondary Accession NumbersNone
Metabolite Identification
Common NameFAD
DescriptionFAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
Structure
Thumb
Synonyms
  1. 1H-Purin-6-amine flavin dinucleotide
  2. 1H-Purin-6-amine flavine dinucleotide
  3. Adenine-flavin dinucleotide
  4. Adenine-flavine dinucleotide
  5. Adenine-riboflavin dinuceotide
  6. Adenine-riboflavin dinucleotide
  7. Adenine-riboflavine dinucleotide
  8. FAD
  9. Flamitajin B
  10. Flanin F
  11. Flavin adenine dinucleotide
  12. Flavin adenine dinucleotide oxidized
  13. Flavin-adenine dinucleotide
  14. Flavine adenosine diphosphate
  15. Flavine-adenine dinucleotide
  16. Flavitan
  17. Flaziren
  18. Isoalloxazine-adenine dinucleotide
  19. Riboflavin 5'-adenosine diphosphate
  20. Riboflavin-adenine dinucleotide
  21. Riboflavine-adenine dinucleotide
Chemical FormulaC27H33N9O15P2
Average Molecular Weight785.5497
Monoisotopic Molecular Weight785.157134455
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
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-3H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry Number146-14-5
SMILES
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(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
InChI Identifier
InChI=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
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassFlavin Nucleotides
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • flavin adenine dinucleotide(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Disaccharide Phosphate
  • Flavin
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Isoalloxazine
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Disaccharide
  • Phosphoric Acid Ester
  • Pteridine
  • Purine
  • Purine Ribonucleoside Diphosphate
  • Pyrazine
  • Pyrimidine
  • Pyrimidone
  • Quinoxaline
  • Saccharide
  • Secondary Alcohol
  • Toluene
Direct ParentFlavin Nucleotides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Enzyme cofactor
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.25 g/LALOGPS
logP-0.78ALOGPS
logP-5.3ChemAxon
logS-2.3ALOGPS
pKa (strongest acidic)1.86ChemAxon
pKa (strongest basic)4.99ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count19ChemAxon
hydrogen donor count9ChemAxon
polar surface area356.42ChemAxon
rotatable bond count13ChemAxon
refractivity177.43ChemAxon
polarizability70.11ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Erythrocyte
  • Liver
  • Muscle
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057map00020
Glycerol Phosphate ShuttleSMP00124Not Available
Riboflavin MetabolismSMP00070map00740
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.061 (0.044-0.078) uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.078 +/- 0.054 uMAdolescent (13-18 years old)FemaleNormal
BloodDetected and Quantified0.075 (0.056-0.097) uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.031 +/- 0.01 uMChildren (1-13 year old)BothSeverely malnourished children
BloodDetected and Quantified0.048 +/- 0.023 uMAdolescent (13-18 years old)FemaleAnorexia nervosa
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  • Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. Pubmed: 10197568
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022511
KNApSAcK IDNot Available
Chemspider ID559059
KEGG Compound IDC00016
BioCyc IDFAD
BiGG ID33521
Wikipedia LinkFAD
NuGOwiki LinkHMDB01248
Metagene LinkHMDB01248
METLIN ID6106
PubChem Compound643975
PDB IDFAD
ChEBI ID16238
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Flatz G, Simmersbach F: Flavin adenine dinucleotide concentration in erythrocytes with normal and deficient glucose-6-phosphate dehydrogenase. Klin Wochenschr. 1970 Sep 1;48(17):1071-2. Pubmed: 5523465
  2. Zempleni J: Determination of riboflavin and flavocoenzymes in human blood plasma by high-performance liquid chromatography. Ann Nutr Metab. 1995;39(4):224-6. Pubmed: 8546438
  3. Becker K, Wilkinson AR: Flavin adenine dinucleotide levels in erythrocytes of very low birthweight infants under vitamin supplementation. Biol Neonate. 1993;63(2):80-5. Pubmed: 8448258
  4. Lisowsky T, Lee JE, Polimeno L, Francavilla A, Hofhaus G: Mammalian augmenter of liver regeneration protein is a sulfhydryl oxidase. Dig Liver Dis. 2001 Mar;33(2):173-80. Pubmed: 11346147
  5. Cimino JA, Jhangiani S, Schwartz E, Cooperman JM: Riboflavin metabolism in the hypothyroid human adult. Proc Soc Exp Biol Med. 1987 Feb;184(2):151-3. Pubmed: 3809170
  6. Kodentsova VM, Vrzhesinskaia OA, Alekseeva IA, Spirichev VB: [Comparison of biochemical criteria for supplying the human body with riboflavin] Vopr Med Khim. 1991 Sep-Oct;37(5):76-9. Pubmed: 1759408
  7. Lopez-Anaya A, Mayersohn M: Quantification of riboflavin, riboflavin 5'-phosphate and flavin adenine dinucleotide in plasma and urine by high-performance liquid chromatography. J Chromatogr. 1987 Dec 25;423:105-13. Pubmed: 3443641
  8. Van Binsbergen CJ, Odink J, Van den Berg H, Koppeschaar H, Coelingh Bennink HJ: Nutritional status in anorexia nervosa: clinical chemistry, vitamins, iron and zinc. Eur J Clin Nutr. 1988 Nov;42(11):929-37. Pubmed: 3074921
  9. Mohrenweiser HW, Novotny JE: ACP1GUA-1--a low-activity variant of human erythrocyte acid phosphatase: association with increased glutathione reductase activity. Am J Hum Genet. 1982 May;34(3):425-33. Pubmed: 7081221
  10. Gianazza E, Vergani L, Wait R, Brizio C, Brambilla D, Begum S, Giancaspero TA, Conserva F, Eberini I, Bufano D, Angelini C, Pegoraro E, Tramontano A, Barile M: Coordinated and reversible reduction of enzymes involved in terminal oxidative metabolism in skeletal muscle mitochondria from a riboflavin-responsive, multiple acyl-CoA dehydrogenase deficiency patient. Electrophoresis. 2006 Mar;27(5-6):1182-98. Pubmed: 16470778
  11. Cimino JA, Noto RA, Fusco CL, Cooperman JM: Riboflavin metabolism in the hypothyroid newborn. Am J Clin Nutr. 1988 Mar;47(3):481-3. Pubmed: 3348160

Only showing the first 50 proteins. There are 166 proteins in total.

Enzymes

Gene Name:
ACADL
Uniprot ID:
P28330
Reactions
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Octanoyl-CoA + FAD unknown (2E)-Octenoyl-CoA + FADHdetails
Lauroyl-CoA + FAD unknown (2E)-Dodecenoyl-CoA + FADHdetails
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Hexanoyl-CoA + FAD unknown trans-2-Hexenoyl-CoA + FADHdetails
Decanoyl-CoA (n-C10:0CoA) + FAD unknown (2E)-Decenoyl-CoA + FADHdetails
Gene Name:
ACADS
Uniprot ID:
P16219
Reactions
Butyryl-CoA + FAD unknown FADH + (E)-but-2-enoyl-CoAdetails
Hexanoyl-CoA + FAD unknown trans-2-Hexenoyl-CoA + FADHdetails
Gene Name:
ACADM
Uniprot ID:
P11310
Reactions
Propionyl-CoA + FAD unknown FADH + Acrylyl-CoAdetails
Butyryl-CoA + FAD unknown FADH + (E)-but-2-enoyl-CoAdetails
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Octanoyl-CoA + FAD unknown (2E)-Octenoyl-CoA + FADHdetails
Lauroyl-CoA + FAD unknown (2E)-Dodecenoyl-CoA + FADHdetails
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Isovaleryl-CoA + FAD unknown 3-Methylcrotonyl-CoA + FADHdetails
Hexanoyl-CoA + FAD unknown trans-2-Hexenoyl-CoA + FADHdetails
Decanoyl-CoA (n-C10:0CoA) + FAD unknown (2E)-Decenoyl-CoA + FADHdetails
Gene Name:
MT-ND1
Uniprot ID:
P03886
Gene Name:
ENPP1
Uniprot ID:
P22413
Reactions
FAD + Water unknown Adenosine monophosphate + Flavin Mononucleotidedetails
Gene Name:
PIPOX
Uniprot ID:
Q9P0Z9
Gene Name:
CYB5R3
Uniprot ID:
P00387
Gene Name:
AOX1
Uniprot ID:
Q06278
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Gene Name:
TXNRD1
Uniprot ID:
Q16881
Gene Name:
SC5DL
Uniprot ID:
O75845
Gene Name:
ACOX1
Uniprot ID:
Q15067
Reactions
Butyryl-CoA + FAD unknown FADH + (E)-but-2-enoyl-CoAdetails
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Octanoyl-CoA + FAD unknown (2E)-Octenoyl-CoA + FADHdetails
Lauroyl-CoA + FAD unknown (2E)-Dodecenoyl-CoA + FADHdetails
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Hexanoyl-CoA + FAD unknown trans-2-Hexenoyl-CoA + FADHdetails
Decanoyl-CoA (n-C10:0CoA) + FAD unknown (2E)-Decenoyl-CoA + FADHdetails
OPC8-CoA + FAD unknown trans-2-Enoyl-OPC8-CoA + FADHdetails
OPC6-CoA + FAD unknown trans-2-Enoyl-OPC6-CoA + FADHdetails
OPC4-CoA + FAD unknown trans-2-Enoyl-OPC4-CoA + FADHdetails
Tetracosahexaenoyl CoA + FAD unknown Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA + FADHdetails
Tetracosapentaenoyl coenzyme A, n-6 + FAD unknown (2E,6Z,9Z,12Z,15Z,18Z)-Tetracosahexa-2,6,9,12,15,18-enoyl-CoA + FADHdetails
Gene Name:
DDO
Uniprot ID:
Q99489
Gene Name:
HMOX2
Uniprot ID:
P30519
Reactions
Hemoglobin + FADH + Oxygen unknown Globin + Biliverdin + Carbon monoxide + Fe3+ + FAD + Waterdetails
Gene Name:
SQLE
Uniprot ID:
Q14534
Gene Name:
MT-ND2
Uniprot ID:
P03891
Gene Name:
TXNRD2
Uniprot ID:
Q9NNW7
Gene Name:
MTR
Uniprot ID:
Q99707
Gene Name:
MAOB
Uniprot ID:
P27338
Gene Name:
ACOX2
Uniprot ID:
Q99424
Gene Name:
IVD
Uniprot ID:
P26440
Reactions
Isovaleryl-CoA + FAD unknown 3-Methylcrotonyl-CoA + FADHdetails

Only showing the first 50 proteins. There are 166 proteins in total.