flavin adenine dinucleotide   

GtoPdb Ligand ID: 5184

Abbreviated name: FAD
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 21
Hydrogen bond donors 9
Rotatable bonds 13
Topological polar surface area 382.55
Molecular weight 785.16
XLogP -2.71
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Canonical SMILES O=c1[nH]c(=O)c2c(n1)n(CC(C(C(COP(=O)(OP(=O)(OCC1OC(C(C1O)O)n1cnc3c1ncnc3N)O)O)O)O)O)c1c(n2)cc(c(c1)C)C
Isomeric SMILES O=c1[nH]c(=O)c2c(n1)n(C[C@@H]([C@@H]([C@@H](COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc3c1ncnc3N)O)O)O)O)O)c1c(n2)cc(c(c1)C)C
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
InChI Key VWWQXMAJTJZDQX-UYBVJOGSSA-N
Classification
Compound class Metabolite or derivative
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)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
Database Links
CAS Registry No. 146-14-5 (source: Scifinder)
ChEBI CHEBI:24040
ChEMBL Ligand CHEMBL1232653
DrugBank Ligand DB03147
GtoPdb PubChem SID 53801068
PubChem CID 643975
RCSB PDB Ligand FAD
Search Google for chemical match using the InChIKey VWWQXMAJTJZDQX-UYBVJOGSSA-N
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Search UniChem for chemicals with the same backbone VWWQXMAJTJZDQX
Wikipedia Flavin_adenine_dinucleotide