riboflavin   

GtoPdb Ligand ID: 6578

Comment: Riboflavin (vitamin B2) is a water-soluble vitamin that is required for the biosynthesis of flavin-derived enzyme cofactors that are essential for cellular respiration. Taken as a dietary supplement to combat vitamin B2 deficiency.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 161.56
Molecular weight 376.14
XLogP 0.58
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(C(C(Cn1c2cc(C)c(cc2nc2c1nc(=O)[nH]c2=O)C)O)O)O
Isomeric SMILES OC[C@H]([C@H]([C@H](Cn1c2cc(C)c(cc2nc2c1nc(=O)[nH]c2=O)C)O)O)O
InChI InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
InChI Key AUNGANRZJHBGPY-SCRDCRAPSA-N
Classification
Compound class Metabolite or derivative
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
Database Links
CAS Registry No. 83-88-5 (source: Scifinder)
ChEBI CHEBI:17015
ChEMBL Ligand CHEMBL1534
DrugCentral Ligand 2834
GtoPdb PubChem SID 178103192
PubChem CID 493570
RCSB PDB Ligand RBF
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Wikipedia Riboflavin