IMPPAT Phytochemical information: 
Alizarin
Alizarin
Summary

SMILES: O=C1c2ccccc2C(=O)c2c1ccc(c2O)O
InChI: InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
InChIKey: RGCKGOZRHPZPFP-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6C=O)cc%10cccc6O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CCCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCCC12
Functional groups: cC(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
free alizarin, alizarin
External chemical identifiers:
CID:CID_6293; ChEMBL:CHEMBL55814; ChEBI:CHEBI:16866; ZINC:ZINC000003860973; FDASRS:60MEW57T9G; SureChEMBL:SCHEMBL18614; MolPort-001-783-920
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Alizarin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 240.21
Log P RDKit 1.87
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 4
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 14
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 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Alizarin
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 0.588111
Alizarin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.52
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Alizarin
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_001676ENSG00000165392WRN7486NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000705ENSG00000126457PRMT13276NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001100ENSG00000171314PGAM15223ChEMBL
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_001127ENSG00000262785PKLR5313ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000290ENSG00000196730DAPK11612BindingDB, ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001630ENSG00000074319TSG1017251NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001165ENSG00000241119UGT1A954600ChEMBL, NPASS
TAR_EXP_001163ENSG00000167165UGT1A654578ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_001929ENSG00000079999KEAP19817NPASS
TAR_EXP_001359ENSG00000171791BCL2596ChEMBL, NPASS