CHEBI:16238 - FAD

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name FAD
ChEBI ID CHEBI:16238
Definition A flavin adenine dinucleotide in which the substituent at position 10 of the flavin nucleus is a 5'-adenosyldiphosphoribityl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42388, CHEBI:4956, CHEBI:13315, CHEBI:21125
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C27H33N9O15P2
Net Charge 0
Average Mass 785.55010
Monoisotopic Mass 785.157
InChI 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
InChIKey VWWQXMAJTJZDQX-UYBVJOGSSA-N
SMILES Cc1cc2nc3c(nc(=O)[nH]c3=O)n(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)n3cnc4c(N)ncnc34)c2cc1C
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
(via flavin adenine dinucleotide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing FAD (CHEBI:16238) has role Escherichia coli metabolite (CHEBI:76971)
FAD (CHEBI:16238) has role human metabolite (CHEBI:77746)
FAD (CHEBI:16238) has role mouse metabolite (CHEBI:75771)
FAD (CHEBI:16238) has role prosthetic group (CHEBI:26348)
FAD (CHEBI:16238) is a flavin adenine dinucleotide (CHEBI:24040)
FAD (CHEBI:16238) is conjugate acid of FAD(3−) (CHEBI:57692)
Incoming FAD(3−) (CHEBI:57692) is conjugate base of FAD (CHEBI:16238)
IUPAC Name
adenosine 5'-(3-{D-ribo-5-[7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-2,3,4-trihydroxypentyl} dihydrogen diphosphate)
Synonyms Sources
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine ChemIDplus
adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate] ChEBI
FAD KEGG COMPOUND
Flavin adenine dinucleotide KEGG COMPOUND
FLAVIN-ADENINE DINUCLEOTIDE PDBeChem
Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine ChemIDplus
Riboflavin 5'-adenosine diphosphate ChemIDplus
Database Links Databases
C00001500 KNApSAcK
C00016 KEGG COMPOUND
D00005 KEGG DRUG
DB03147 DrugBank
FAD PDBeChem
MOL000039 COMe
View more database links
Registry Numbers Types Sources
108834 Gmelin Registry Number Gmelin
1208946 Beilstein Registry Number Beilstein
146-14-5 CAS Registry Number KEGG COMPOUND
146-14-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
24643482 PubMed citation Europe PMC
25108762 PubMed citation Europe PMC
Last Modified
16 February 2017