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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 15:02:25 UTC
Update Date2021-09-14 15:00:06 UTC
HMDB IDHMDB0011612
Secondary Accession Numbers
  • HMDB11612
Metabolite Identification
Common Name6-Hydroxy flavin adenine dinucleotide
Description6-Hydroxy flavin adenine dinucleotide, also known as 6-HO-fad, 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. 6-Hydroxy flavin adenine dinucleotide has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 6-hydroxy flavin adenine dinucleotide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 6-Hydroxy flavin adenine dinucleotide.
Structure
Thumb
Synonyms
ValueSource
6-HO-FADChEBI
6-HYDROXY-flavin-adenine dinucleotideChEBI
6-Hydroxyflavin-adenine dinucleotideChEBI
6-Hydroxyflavine-adenine dinucleotideChEBI
6-Hydroxyriboflavin 5'-(trihydrogen diphosphate) 5'->5'-ester with adenosineChEBI
6-OH-FadChEBI
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentyl dihydrogen diphosphateChEBI
Adenosine 5'-(trihydrogen diphosphate) 5'->5'-ester with 6-hydroxyriboflavinChEBI
6-Hydroxyriboflavin 5'-(trihydrogen diphosphoric acid) 5'->5'-ester with adenosineGenerator
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentyl dihydrogen diphosphoric acidGenerator
Adenosine 5'-(trihydrogen diphosphoric acid) 5'->5'-ester with 6-hydroxyriboflavinGenerator
6-Hydroxy-7,8-dimethyl-10-(ribityl-5'-ADP)-isoalloxazineHMDB
6-Hydroxy-fadHMDB
Chemical FormulaC27H33N9O16P2
Average Molecular Weight801.5491
Monoisotopic Molecular Weight801.152049077
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S)-2,3,4-trihydroxy-5-{6-hydroxy-7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}pentyl]oxy})phosphinic acid
Traditional Name6-hydroxy-fad
CAS Registry Number52301-43-6
SMILES
CC1=C(C)C(O)=C2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)C2=C1
InChI Identifier
InChI=1S/C27H33N9O16P2/c1-9-3-11-15(18(39)10(9)2)32-17-24(33-27(44)34-25(17)43)35(11)4-12(37)19(40)13(38)5-49-53(45,46)52-54(47,48)50-6-14-20(41)21(42)26(51-14)36-8-31-16-22(28)29-7-30-23(16)36/h3,7-8,12-14,19-21,26,37-42H,4-6H2,1-2H3,(H,45,46)(H,47,48)(H2,28,29,30)(H,34,43,44)/t12-,13+,14+,19-,20+,21+,26+/m0/s1
InChI KeyBJSUUWFQAMLNKU-OKXKTURISA-N
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
  • Organic pyrophosphate
  • 6-aminopurine
  • Diazanaphthalene
  • Pentose monosaccharide
  • Pteridine
  • Quinoxaline
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02654
Phenol Explorer Compound IDNot Available
FooDB IDFDB028318
KNApSAcK IDNot Available
Chemspider ID16743795
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5287546
PDB ID6FA
ChEBI ID40260
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marshall KR, Gong M, Wodke L, Lamb JH, Jones DJ, Farmer PB, Scrutton NS, Munro AW: The human apoptosis-inducing protein AMID is an oxidoreductase with a modified flavin cofactor and DNA binding activity. J Biol Chem. 2005 Sep 2;280(35):30735-40. Epub 2005 Jun 15. [PubMed:15958387 ]