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; cn(C)c; cnc; c=O; c[nH]c
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:
vitamin b2, riboflavin, riboflavine
External chemical identifiers:
CID:CID_493570; ChEMBL:CHEMBL1534; ChEBI:CHEBI:17015; ZINC:ZINC000002036848; FDASRS:TLM2976OFR; SureChEMBL:SCHEMBL7706; MolPort-003-934-329
Chemical structure download


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
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 0.328412


Riboflavin
ADME 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
Number of Brenk structural alerts SwissADME 1
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001261ENSG00000100567PSMA35684ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_001275ENSG00000136930PSMB75695ChEMBL
TAR_EXP_001276ENSG00000235715PSMB85696ChEMBL
TAR_EXP_001277ENSG00000239836PSMB95698ChEMBL
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000724ENSG00000144381HSPD13329ChEMBL, NPASS
TAR_EXP_000725ENSG00000115541HSPE13336ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_001278ENSG00000205220PSMB105699ChEMBL
TAR_EXP_001352ENSG00000102054RBBP75931ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_000174ENSG00000222028PSMB11122706ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000138ENSG00000162438CTRC11330ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001557ENSG00000012048BRCA1672ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001616ENSG00000228321TNF7124NPASS
TAR_EXP_001633ENSG00000128311TST7263ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001789ENSG00000292096HAT18520ChEMBL
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001259ENSG00000129084PSMA15682ChEMBL
TAR_EXP_001260ENSG00000106588PSMA25683ChEMBL
TAR_EXP_001262ENSG00000041357PSMA45685ChEMBL
TAR_EXP_001263ENSG00000143106PSMA55686ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000223ENSG00000154611PSMA8143471ChEMBL
TAR_EXP_001265ENSG00000101182PSMA75688ChEMBL
TAR_EXP_001264ENSG00000100902PSMA65687ChEMBL
TAR_EXP_001267ENSG00000126067PSMB25690ChEMBL
TAR_EXP_001269ENSG00000277791PSMB35691ChEMBL
TAR_EXP_001270ENSG00000159377PSMB45692ChEMBL
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL
TAR_EXP_001274ENSG00000142507PSMB65694ChEMBL
TAR_EXP_001266ENSG00000008018PSMB15689ChEMBL