IMPPAT Phytochemical information: 
2-Hydroxy-1,4-naphthoquinone
2-Hydroxy-1,4-naphthoquinone
Summary

SMILES: O=C1C=C(O)c2c(C1=O)cccc2
InChI: InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,11H
InChIKey: WVCHIGAIXREVNS-UHFFFAOYSA-N
DeepSMILES: O=CC=CO)ccC6=O))cccc6
Scaffold Graph/Node/Bond level: O=C1C=Cc2ccccc2C1=O
Scaffold Graph/Node level: OC1CCC2CCCCC2C1O
Scaffold Graph level: CC1CCC2CCCCC2C1C
Functional groups: O=C1C=C(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-hydroxy-α-naphthaquinone(lawsone), lawsone, Lawsone, lawsone(2-hydroxy-1:4-naphthaquinone), hennotannic acid
External chemical identifiers:
CID:CID_6755; ZINC:ZINC000100034686; SureChEMBL:SCHEMBL342409
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Hydroxy-1,4-naphthoquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 174.16
Log P RDKit 1.35
Topological polar surface area (Å2) RDKit 54.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 3
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 0
Shape complexity RDKit 0
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
2-Hydroxy-1,4-naphthoquinone
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 Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.603789
2-Hydroxy-1,4-naphthoquinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.76
Number of PAINS structural alerts SwissADME 2
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
2-Hydroxy-1,4-naphthoquinone
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_000616ENSG00000111700SLCO1B328234ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL
TAR_EXP_001663ENSG00000162607USP17398ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000887ENSG00000118113MMP84317ChEMBL
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000564ENSG00000134242PTPN2226191ChEMBL
TAR_EXP_000500ENSG00000275565ALOX5240ChEMBL
TAR_EXP_000885ENSG00000149968MMP34314ChEMBL