IMPPAT Phytochemical information: 
Rotenone
Rotenone
Summary

SMILES: COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(=C)C
InChI: InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
InChIKey: JUVIOZPCNVVQFO-HBGVWJBISA-N
DeepSMILES: COcccccc6OC))))OC[C@@H][C@H]6C=O)ccO6)cC[C@@H]Oc5cc9))))C=C)C
Scaffold Graph/Node/Bond level: O=C1c2ccc3c(c2OC2COc4ccccc4C12)CCO3
Scaffold Graph/Node level: OC1C2CCC3OCCC3C2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCC3CCCC3C2CC2CCC3CCCCC3C21
Functional groups: C=C(C)C; cC(C)=O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Rotenoids
Synonymous chemical names:
rotenone
External chemical identifiers:
CID:6758; ChEMBL:CHEMBL429023; ChEBI:28201; ZINC:ZINC000003860715; FDASRS:03L9OT429T; SureChEMBL:SCHEMBL42253; MolPort-002-507-351
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rotenone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Rotenone
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74
Rotenone
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.79
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Rotenone
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1700
ENSP00000216117HMOX1846
ENSP00000216185TXN2786
ENSP00000216254ACO2738
ENSP00000219070MMP2700
ENSP00000222553NAMPT700
ENSP00000225740ALDH3A1786
ENSP00000229135IFNG700
ENSP00000229794MAPK14757
ENSP00000234111ODC1938
ENSP00000256383EIF2S1700
ENSP00000258743IL6733
ENSP00000260433CYP19A1735
ENSP00000261623CYBA894
ENSP00000262186KCNH2700
ENSP00000263025MAPK3725
ENSP00000264613CP700
ENSP00000270349SLC6A3859
ENSP00000278379SLC1A2800
ENSP00000295550COL6A3700
ENSP00000297350TNFRSF11B700
ENSP00000297785ALDH1A1804
ENSP00000298472SLC18A2954
ENSP00000298910LRRK2874
ENSP00000306330YWHAG700
ENSP00000307235EIF2AK3725
ENSP00000309103BAD700
ENSP00000309477ACO1788
ENSP00000311032CASP3796
ENSP00000311127VEGFB800
ENSP00000312652LEP721
ENSP00000314458CDC42800
ENSP00000327251NOS2733
ENSP00000327801P4HB800
ENSP00000327850NFATC1800
ENSP00000329623BCL2728
ENSP00000330237CASP9737
ENSP00000337459NOS1786
ENSP00000338345SNCA988
ENSP00000340278PARK7895
ENSP00000343204JAK1700
ENSP00000346697BMF784
ENSP00000346839FN1700
ENSP00000347942RET800
ENSP00000353483MAPK8770
ENSP00000353701DPP3700
ENSP00000354665MT-ND6797
ENSP00000354687MT-ND1890
ENSP00000354961MT-ND4821
ENSP00000355317WDTC1864
ENSP00000355370CNTF700
ENSP00000355759PARP1945
ENSP00000355865PARK2857
ENSP00000356022SOD2813
ENSP00000358327CASP7738
ENSP00000360266JUN735
ENSP00000360492NDUFA1878
ENSP00000364204PINK1859
ENSP00000368727XDH749
ENSP00000371067JAK2700
ENSP00000374455SQSTM1764
ENSP00000380252NFE2L2728
ENSP00000416293SLC2A1736
ENSP00000447173VDR700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.