| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:10 -0700 |
| HMDB ID |
HMDB01248 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
FAD |
| Description |
FAD 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1H-Purin-6-amine flavin dinucleotide
- 1H-Purin-6-amine flavine dinucleotide
- Adenine-flavin dinucleotide
- Adenine-flavine dinucleotide
- Adenine-riboflavin dinuceotide
- Adenine-riboflavin dinucleotide
- Adenine-riboflavine dinucleotide
- FAD
- Flamitajin B
- Flanin F
- Flavin adenine dinucleotide
- Flavin adenine dinucleotide oxidized
- Flavin-adenine dinucleotide
- Flavine adenosine diphosphate
- Flavine-adenine dinucleotide
- Flavitan
- Flaziren
- Isoalloxazine-adenine dinucleotide
- Riboflavin 5'-adenosine diphosphate
- Riboflavin-adenine dinucleotide
- Riboflavine-adenine dinucleotide
|
| Chemical Formula |
C27H33N9O15P2 |
| Average Molecular Weight |
785.5497 |
| Monoisotopic Molecular Weight |
785.157134455 |
| 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 Number |
146-14-5 |
| 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 Key |
VWWQXMAJTJZDQX-UYBVJOGSSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Flavin Nucleotides |
| Sub Class |
N/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 Parent |
Flavin Nucleotides |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Mitochondria
- Endoplasmic reticulum
- Peroxisome
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
5 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Mitochondria
- Endoplasmic reticulum
- Peroxisome
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| Biofluid Locations |
|
| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.061 (0.044-0.078) uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.078 +/- 0.054 uM |
Adolescent (13-18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.075 (0.056-0.097) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
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| Blood |
Detected and Quantified |
|
0.031 +/- 0.01 uM |
Children (1-13 year old) |
Both |
Severely malnourished children |
Not Available |
| Blood |
Detected and Quantified |
|
0.048 +/- 0.023 uM |
Adolescent (13-18 years old) |
Female |
Anorexia nervosa |
Not Available |
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| 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
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| Associated OMIM IDs |
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| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022511 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
559059  |
| KEGG Compound ID |
C00016  |
| BioCyc ID |
FAD  |
| BiGG ID |
33521  |
| Wikipedia Link |
FAD  |
| NuGOwiki Link |
HMDB01248  |
| Metagene Link |
HMDB01248  |
| METLIN ID |
6106  |
| PubChem Compound |
643975  |
| PDB ID |
FAD  |
| ChEBI ID |
16238  |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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| Enzymes |
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| Name: |
Aldehyde oxidase
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| Reactions: |
- an aldehyde + H2O + O2 = a carboxylic acid + H2O2 [RN:R00635]
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| Gene Name: |
AOX1 |
| Uniprot ID: |
Q06278  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lathosterol oxidase
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| Reactions: |
- 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [RN:R03310 R07215]
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| Gene Name: |
SC5DL |
| Uniprot ID: |
O75845  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
D-aspartate oxidase
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| Reactions: |
- D-aspartate + H2O + O2 = oxaloacetate + NH3 + H2O2 [RN:R00359]
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| Gene Name: |
DDO |
| Uniprot ID: |
Q99489  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Heme oxygenase 2
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| Reactions: |
- heme + 3 AH2 + 3 O2 = biliverdin + Fe2+ + CO + 3 A + 3 H2O [RN:R00311]
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| Gene Name: |
HMOX2 |
| Uniprot ID: |
P30519  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Methionine synthase
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| Reactions: |
- 5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine [RN:R00946]
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| Gene Name: |
MTR |
| Uniprot ID: |
Q99707  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Peroxisomal acyl-coenzyme A oxidase 2
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| Reactions: |
- (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA + H2O + acceptor = (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26- oyl-CoA + reduced acceptor [RN:R07374]
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| Gene Name: |
ACOX2 |
| Uniprot ID: |
Q99424  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Heme oxygenase 1
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| Reactions: |
- heme + 3 AH2 + 3 O2 = biliverdin + Fe2+ + CO + 3 A + 3 H2O [RN:R00311]
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| Gene Name: |
HMOX1 |
| Uniprot ID: |
P09601  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
D-amino-acid oxidase
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| Reactions: |
- a D-amino acid + H2O + O2 = a 2-oxo acid + NH3 + H2O2 [RN:R01340]
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| Gene Name: |
DAO |
| Uniprot ID: |
P14920  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Methionine synthase reductase
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| Reactions: |
- 2 [methionine synthase]-methylcob(I)alamin + 2 S-adenosylhomocysteine + NADP+ = 2 [methionine synthase]-cob(II)alamin + NADPH + H+ + 2 S-adenosyl-L-methionine [RN:R05182]
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| Gene Name: |
MTRR |
| Uniprot ID: |
Q9UBK8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Spermine oxidase
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| Reactions: |
- spermine + O2 + H2O = spermidine + 3-aminopropanal + H2O2 [RN:R09076]
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| Gene Name: |
SMOX |
| Uniprot ID: |
Q9NWM0  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Dual oxidase 2
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| Reactions: |
- NAD(P)H + H+ + O2 = NAD(P)+ + H2O2 [RN:R07171 R07172]
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| Gene Name: |
DUOX2 |
| Uniprot ID: |
Q9NRD8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Dual oxidase 1
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| Reactions: |
- NAD(P)H + H+ + O2 = NAD(P)+ + H2O2 [RN:R07171 R07172]
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| Gene Name: |
DUOX1 |
| Uniprot ID: |
Q9NRD9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
FAD synthase
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| Reactions: |
- ATP + FMN = diphosphate + FAD [RN:R00161]
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| Gene Name: |
FLAD1 |
| Uniprot ID: |
Q8NFF5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
L-amino-acid oxidase
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| Reactions: |
- an L-amino acid + H2O + O2 = a 2-oxo acid + NH3 + H2O2 [RN:R01259]
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| Gene Name: |
IL4I1 |
| Uniprot ID: |
Q96RQ9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Prenylcysteine oxidase 1
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| Reactions: |
- an S-prenyl-L-cysteine + O2 + H2O = a prenal + L-cysteine + H2O2 [RN:R07360]
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| Gene Name: |
PCYOX1 |
| Uniprot ID: |
Q9UHG3  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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