IMPPAT Phytochemical information: 
Rhein
Rhein
Summary

SMILES: Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1O)C(=O)O
InChI: InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
InChIKey: FCDLCPWAQCPTKC-UHFFFAOYSA-N
DeepSMILES: Occcccc6C=O)ccC6=O))cccc6O)))))))))))C=O)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: cO; cC(=O)c; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthracenecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
rhein, 1,8-dihydroxy-3-carboxyanthraquinone, Rhein, rhein (1,8-dihydroxyanthraquinone-3-carboxylic acid)
External chemical identifiers:
CID:CID_10168; ChEMBL:CHEMBL418068; ChEBI:CHEBI:8825; ZINC:ZINC000004098704; FDASRS:YM64C2P6UX; SureChEMBL:SCHEMBL25253; MolPort-001-742-586
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rhein
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.22
Log P RDKit 1.57
Topological polar surface area (Å2) RDKit 111.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
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 15
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
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
Rhein
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.625
Rhein
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.45
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
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
Rhein
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_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001312ENSG00000143851PTPN75778BindingDB, ChEMBL, NPASS
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL, NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_000723ENSG00000096384HSP90AB13326ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000961ENSG00000115488NEU24759BindingDB, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001175ENSG00000091542ALKBH554890ChEMBL
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_000027ENSG00000123374CDK21017BindingDB
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001630ENSG00000074319TSG1017251NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000392ENSG00000157554ERG2078NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_000759ENSG00000169429CXCL83576NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001136ENSG00000178209PLEC5339BindingDB, NPASS
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_001378ENSG00000143365RORC6097ChEMBL, NPASS
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_000608ENSG00000115419GLS2744ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000172ENSG00000189046ALKBH2121642ChEMBL
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_000722ENSG00000080824HSP90AA13320BindingDB, ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_001716ENSG00000140718FTO79068BindingDB, ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_001676ENSG00000165392WRN7486ChEMBL, NPASS
TAR_EXP_000645ENSG00000113580NR3C12908NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000471ENSG00000124523SIRT523408NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000429ENSG00000166199ALKBH3221120BindingDB, ChEMBL
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS