FAD

FLAVIN-ADENINE DINUCLEOTIDE

Created: 1999-07-08
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count86
Chiral Atom Count9
Bond Count91
Aromatic Bond Count16
2D diagram of FAD
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Chemical Component Summary

NameFLAVIN-ADENINE DINUCLEOTIDE
Systematic Name (OpenEye OEToolkits)[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentoxy]-hydroxy-phosphoryl] hydrogen phosphate
FormulaC27 H33 N9 O15 P2
Molecular Weight785.55
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2C3=Nc1cc(c(cc1N(C3=NC(=O)N2)CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC6OC(n5cnc4c(ncnc45)N)C(O)C6O)C)C
SMILESCACTVS3.341Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[CH](O)[CH](O)[CH](O)CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH]([CH](O)[CH]4O)n5cnc6c(N)ncnc56)c2cc1C
SMILESOpenEye OEToolkits1.5.0Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5ncnc6N)O)O)O)O)O
Canonical SMILESCACTVS3.341 Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)c2cc1C
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)n5cnc6c5ncnc6N)O)O)O)O)O
InChIInChI1.03 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
InChIKeyInChI1.03 VWWQXMAJTJZDQX-UYBVJOGSSA-N

Drug Info: DrugBank

DrugBank IDDB03147 
NameFlavin adenine dinucleotide
Groups approved
DescriptionA 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) Flavin adenine dinucleotide is approved for use in Japan under the trade name Adeflavin as an ophthalmic treatment for vitamin B2 deficiency.
Synonyms
  • Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine
  • Riboflavin 5'-adenosine diphosphate
  • Flavin adenine dinucleotide disodium
  • Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine
  • Flavin-Adenine Dinucleotide
Brand Names
  • Enl
  • EnBrace HR
  • PramLyte
  • BumP DHA
  • EnLyte
IndicationUsed to treat eye diseases caused by vitamin B2 deficiency, such as keratitis and blepharitis.
Categories
  • Adenine Nucleotides
  • Biological Factors
  • Coenzymes
  • Enzymes and Coenzymes
  • Flavins
CAS number146-14-5

Drug Targets

NameTarget SequencePharmacological ActionActions
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9, mitochondrialMAAAAQSRVVRVLSMSRSAITAIATSVCHGPPCRQLHHALMPHGKGGRSS...unknowncofactor
p-hydroxybenzoate hydroxylaseMKTQVAIIGAGPSGLLLGQLLHKAGIDNVILERQTPDYVLGRIRAGVLEQ...unknown
Nitric oxide synthase, brainMEDHMFGVQQIQPNVISVRLFKRKVGGLGFLVKERVSKPPVIISDLIRGG...unknown
NAD(P)H dehydrogenase [quinone] 1MVGRRALIVLAHSERTSFNYAMKEAAAAALKKKGWEVVESDLYAMNFNPI...unknown
p-hydroxybenzoate hydroxylaseMKTQVAIIGAGPSGLLLGQLLHKAGIDNVILERQTPDYVLGRIRAGVLEQ...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 643975
ChEMBL CHEMBL1232653
ChEBI CHEBI:16238