IMPPAT Phytochemical information: 
Emodin
Emodin
Summary

SMILES: Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O
InChI: InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
InChIKey: RHMXXJGYXNZAPX-UHFFFAOYSA-N
DeepSMILES: CcccO)ccc6)C=O)ccC6=O))cO)ccc6)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
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:
rheum-emodin, Emodol, emodol, frangula emodin, Rheum-emodin, Emodin, emodin, archin(emodin), Frangula emodin
External chemical identifiers:
CID:CID_3220; ChEMBL:CHEMBL289277; ChEBI:CHEBI:42223; ZINC:ZINC000003824868; FDASRS:KA46RNI6HN; SureChEMBL:SCHEMBL177689; MolPort-000-165-354
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Emodin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 270.24
Log P RDKit 1.89
Topological polar surface area (Å2) RDKit 94.83
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 20
Number of heteroatoms RDKit 5
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
Emodin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.58
Emodin
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.02
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
Emodin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000327251NOS2733
ENSP00000337825LCK818
ENSP00000341045UGT2B15700
ENSP00000343204JAK1700
ENSP00000343838UGT1A10721
ENSP00000343925ESR2763
ENSP00000346768UGT1A9721
ENSP00000371067JAK2700
ENSP00000346839FN1800
ENSP00000320935SLC2A4800
ENSP00000358022MCL1811
ENSP00000361125VEGFA824
ENSP00000361850PLAU800
ENSP00000362525UGT1A7700
ENSP00000362549UGT1A8722
ENSP00000365663NPPA800
ENSP00000350941SRC700
ENSP00000355759PARP1700
ENSP00000407154HSD11B1L712
ENSP00000411532TOP2A700
ENSP00000398698TNF818
ENSP00000206249ESR1763
ENSP00000217244CSNK2A1992
ENSP00000242261TWIST1800
ENSP00000243077LRP1800
ENSP00000260630CYP1B1824
ENSP00000261465HSD11B1786
ENSP00000264657STAT3700
ENSP00000269305TP53819
ENSP00000269571ERBB2822
ENSP00000278616ATM700
ENSP00000284000CEBPG786
ENSP00000296871CSF2800
ENSP00000299421ILK800
ENSP00000304845UGT1A1700
ENSP00000307786CYCS759
ENSP00000311032CASP3945
ENSP00000320709ADIPOQ800
ENSP00000386884CXCR4800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.