IMPPAT Phytochemical information: 
Menadione

Menadione
Summary

SMILES: O=C1C=C(C)C(=O)c2c1cccc2
InChI: InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey: MJVAVZPDRWSRRC-UHFFFAOYSA-N
DeepSMILES: O=CC=CC)C=O)cc6cccc6
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2CCCCC12
Scaffold Graph level: CC1CCC(C)C2CCCCC12
Functional groups: CC1=CC(=O)ccC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
2-methyl-1,4-naphthoquinone, vitamin k3, menadione
External chemical identifiers:
CID:CID_4055; ChEMBL:CHEMBL590; ChEBI:CHEBI:28869; ZINC:ZINC000000001677; FDASRS:723JX6CXY5; SureChEMBL:SCHEMBL25970; MolPort-001-766-699
Chemical structure download


Menadione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 172.18
Log P RDKit 2.01
Topological polar surface area (Å2) RDKit 34.14
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Menadione
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.599483


Menadione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.79
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Menadione
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_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001033ENSG00000011198ABHD551099ChEMBL, NPASS
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001128ENSG00000067225PKM5315NPASS
TAR_EXP_001138ENSG00000166819PLIN15346BindingDB, ChEMBL, NPASS
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001153ENSG00000127948POR5447ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000947ENSG00000149311ATM472NPASS
TAR_EXP_000900ENSG00000214456PLIN5440503BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_001939ENSG00000158402CDC25C995BindingDB, ChEMBL, NPASS
TAR_EXP_001937ENSG00000101224CDC25B994BindingDB, ChEMBL, NPASS
TAR_EXP_001935ENSG00000164045CDC25A993BindingDB, ChEMBL, NPASS
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001654ENSG00000118939UCHL37347BindingDB, ChEMBL, NPASS
TAR_EXP_001653ENSG00000154277UCHL17345BindingDB, NPASS
TAR_EXP_001646ENSG00000176890TYMS7298ChEMBL, NPASS
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001633ENSG00000128311TST7263ChEMBL, NPASS
TAR_EXP_001605ENSG00000198959TGM27052BindingDB
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000766ENSG00000131203IDO13620BindingDB, ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000312ENSG00000181019NQO11728ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL, NPASS
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000725ENSG00000115541HSPE13336ChEMBL, NPASS
TAR_EXP_000724ENSG00000144381HSPD13329ChEMBL, NPASS
TAR_EXP_000721ENSG00000089685BIRC5332ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000693ENSG00000138356AOX1316BindingDB, ChEMBL, NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000679ENSG00000244734HBB3043ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000577ENSG00000115486GGCX2677ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000556ENSG00000111640GAPDH2597NPASS
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000661ENSG00000104687GSR2936ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS