IMPPAT Phytochemical information: 
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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: cOC; cC(=O)C; C=C(C)C
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, Rotenone
External chemical identifiers:
CID:CID_6758; ChEMBL:CHEMBL429023; ChEBI:CHEBI:28201; ZINC:ZINC000003860715; FDASRS:03L9OT429T; SureChEMBL:SCHEMBL42253; MolPort-002-507-351
Chemical structure download


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Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.42
Log P RDKit 3.7
Topological polar surface area (Å2) RDKit 63.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


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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 0.739996


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ADME 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
Number of Brenk structural alerts SwissADME 1
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


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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_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001194ENSG00000132356PRKAA15562ChEMBL
TAR_EXP_001195ENSG00000162409PRKAA25563ChEMBL
TAR_EXP_001196ENSG00000111725PRKAB15564ChEMBL
TAR_EXP_001197ENSG00000131791PRKAB25565ChEMBL
TAR_EXP_001203ENSG00000181929PRKAG15571ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001171ENSG00000132170PPARG5468ChEMBL, NPASS
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL, NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000910ENSG00000198886MT-ND44538BindingDB, ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_001058ENSG00000106617PRKAG251422ChEMBL
TAR_EXP_001140ENSG00000115592PRKAG353632ChEMBL
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_000070ENSG00000172757CFL11072ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL, NPASS
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL, NPASS
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001808ENSG00000276582ABCB118647ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_001684ENSG00000104267CA2760ChEMBL
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL, NPASS
TAR_EXP_001930ENSG00000170312CDK1983ChEMBL