IMPPAT Phytochemical information: 
Chrysophanol
Chrysophanol
Summary

SMILES: Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
InChI: InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
InChIKey: LQGUBLBATBMXHT-UHFFFAOYSA-N
DeepSMILES: CcccO)ccc6)C=O)ccC6=O))cO)ccc6
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CCCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCCC12
Functional groups: cO; cC(=O)c
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:
chrysophanol, archinin(chrysophanic acid), 1,8-dihydroxy-3 methylanthraquinone, chrysophanic-acid, chrysophanic acid, 1,8-dihydroxy-3-methylanthraquinone
External chemical identifiers:
CID:CID_10208; ChEMBL:CHEMBL41092; ChEBI:CHEBI:3687; ZINC:ZINC000003861630; FDASRS:N1ST8V8RR2; SureChEMBL:SCHEMBL308131; MolPort-000-165-353
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Chrysophanol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 254.24
Log P RDKit 2.18
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 15
Number of heavy atoms RDKit 19
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 1
Shape complexity RDKit 0.07
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
Chrysophanol
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 0.644448
Chrysophanol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.34
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 Yes
P-glycoprotein substrate SwissADME No
Chrysophanol
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_000043ENSG00000117448AKR1A110327ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001165ENSG00000241119UGT1A954600ChEMBL, NPASS
TAR_EXP_001163ENSG00000167165UGT1A654578ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000645ENSG00000113580NR3C12908NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991BindingDB, ChEMBL, NPASS
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001557ENSG00000012048BRCA1672NPASS
TAR_EXP_001378ENSG00000143365RORC6097NPASS
TAR_EXP_000385ENSG00000120915EPHX22053ChEMBL, NPASS
TAR_EXP_001499ENSG00000169313P2RY1264805ChEMBL, NPASS