IMPPAT Phytochemical information: 
Riboflavin
Riboflavin
Summary

SMILES: OC[C@H]([C@H]([C@H](Cn1c2-c(nc3c1cc(C)c(c3)C)c(=O)[nH]c(=O)n2)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
InChIKey: AUNGANRZJHBGPY-SCRDCRAPSA-N
DeepSMILES: OC[C@H][C@H][C@H]Cnc-cncc6ccC)cc6)C)))))))c=O)[nH]c=O)n6))))))))O))O))O
Scaffold Graph/Node/Bond level: O=c1nc2[nH]c3ccccc3nc-2c(=O)[nH]1
Scaffold Graph/Node level: OC1NC(O)C2NC3CCCCC3NC2N1
Scaffold Graph level: CC1CC(C)C2CC3CCCCC3CC2C1
Functional groups: CO; c=O; c[nH]c; cn(c)C; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pteridines and derivatives
ClassyFire Subclass: Alloxazines and isoalloxazines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: pteridine alkaloids
Synonymous chemical names:
riboflavin, riboflavine, vitamin b2
External chemical identifiers:
CID:493570; ChEMBL:CHEMBL1534; ChEBI:17015; ZINC:ZINC000002036848; FDASRS:TLM2976OFR; SureChEMBL:SCHEMBL7706; MolPort-003-934-329
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Riboflavin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 376.37
Log P RDKit -1.72
Topological polar surface area (Å2) RDKit 161.56
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Riboflavin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3284
Riboflavin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.63
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Riboflavin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216392PYGL800
ENSP00000217254SLC52A3981
ENSP00000218758ACP5900
ENSP00000221130GSR870
ENSP00000263368BLVRB909
ENSP00000270593ACPT800
ENSP00000272065ACP1800
ENSP00000292180FLAD1919
ENSP00000323036ACPP800
ENSP00000354238ENPP1900
ENSP00000358241ACP6800
ENSP00000365926RFK989
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.