flavin adenine dinucleotide   Click here for help

GtoPdb Ligand ID: 5184

Abbreviated name: FAD
PDB Ligand
Compound class: Metabolite or derivative
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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

For advanced searching click here to open chemical structure editor

Similar Ligands Click here for help
flavin mononucleotide
Click here for ligand page
riboflavin
Click here for ligand page
Targets
Organic cation transporter-like 2; solute carrier family 52 member 1; solute carrier family 52 member 2; solute carrier family 52 member 3