IMPPAT Phytochemical information: 
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Summary

SMILES: COC1=C[C@@H](C)[C@H]2[C@@](C1=O)(C)[C@H]1C(=O)C(=C([C@H]3[C@@]1([C@@H](C2)OC(=O)C3)C)C)OC
InChI: InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1
InChIKey: IOSXSVZRTUWBHC-LBTVDEKVSA-N
DeepSMILES: COC=C[C@@H]C)[C@H][C@@]C6=O))C)[C@H]C=O)C=C[C@H][C@@]6[C@@H]C%10)OC=O)C6))))C)))C))OC
Scaffold Graph/Node/Bond level: O=C1CC2C=CC(=O)C3C4C(=O)C=CCC4CC(O1)C23
Scaffold Graph/Node level: OC1CC2CCC(O)C3C4C(O)CCCC4CC(O1)C23
Scaffold Graph level: CC1CC2CCC(C)C3C4C(C)CCCC4CC(C1)C23
Functional groups: COC(=CC)C(=O)C; COC(=C(C)C)C(=O)C; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
nigakilactone-d, quassin, Quassin
External chemical identifiers:
CID:CID_65571; ChEMBL:CHEMBL517016; ChEBI:CHEBI:8692; ZINC:ZINC000003978633; FDASRS:QP1YAK6QGK; SureChEMBL:SCHEMBL140454; MolPort-039-052-556
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.46
Log P RDKit 2.82
Topological polar surface area (Å2) RDKit 78.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Drug-likeness properties
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 0.677081
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.98
Number of PAINS structural alerts SwissADME 0
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 Yes
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000255262NMUR2900
ENSP00000255008SSTR4900
ENSP00000254235ADCY7900
ENSP00000257254APLNR900
ENSP00000257497ANXA1900
ENSP00000259607CCL21900
ENSP00000259631CCL27900
ENSP00000260600ADCY3900
ENSP00000264218NMU900
ENSP00000256906HRH4900
ENSP00000257068MTNR1B900
ENSP00000267377SSTR1900
ENSP00000249041GALR3900
ENSP00000264708POMC900
ENSP00000014930HEBP1900
ENSP00000176183DRD4900
ENSP00000216629BDKRB1900
ENSP00000217305PDYN900
ENSP00000223642C5900
ENSP00000225992PPY900
ENSP00000226317CXCL6900
ENSP00000231188GRM6900
ENSP00000234961OPRD1900
ENSP00000249284TAS2R16900
ENSP00000240615TAS2R8900
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000242152NPY900
ENSP00000245907C3900
ENSP00000246115S1PR4900
ENSP00000246657CCR7900
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000249016MCHR1900
ENSP00000240619TAS2R10900
ENSP00000265023KNG1900
ENSP00000301908PNOC900
ENSP00000265643GAL900
ENSP00000356429RGS1900
ENSP00000356430RGS18900
ENSP00000357301RXFP4900
ENSP00000358099RGS10900
ENSP00000358511CNR1900
ENSP00000358730ADORA3900
ENSP00000358783NPBWR2900
ENSP00000355627AGT900
ENSP00000358867GNAI3900
ENSP00000359643LPAR3900
ENSP00000360973AGTR2900
ENSP00000362795CXCR3900
ENSP00000363296GRM4900
ENSP00000363431NPY4R900
ENSP00000363596CNR2900
ENSP00000363643P2RY4900
ENSP00000358963HTR1B900
ENSP00000366061NMS900
ENSP00000355523RGS7900
ENSP00000355156SUCNR1900
ENSP00000344173GRM8900
ENSP00000347197C5AR1900
ENSP00000348918SAA1900
ENSP00000349003PTGER3900
ENSP00000349478HCAR1900
ENSP00000350198SSTR2900
ENSP00000350256CCR9900
ENSP00000355316GRM3900
ENSP00000350348GRM7900
ENSP00000265572OPRK1900
ENSP00000351755LPAR1900
ENSP00000353198PYY900
ENSP00000354416CCL28900
ENSP00000354652NPY1R900
ENSP00000354859DRD2900
ENSP00000354901CXCL9900
ENSP00000350878S1PR3900
ENSP00000367869900
ENSP00000367930OXER1900
ENSP00000371932TAS2R1900
ENSP00000409378CHRM4900
ENSP00000419361ADCY5900
ENSP00000420194CASR900
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2900
ENSP00000431719TAS2R43900
ENSP00000436450TAS2R46900
ENSP00000405095TAS2R39900
ENSP00000436714HCAR3900
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000444736TAS2R30900
ENSP00000448219TAS2R38900
ENSP00000451030RGS6900
ENSP00000466933S1PR2900
ENSP00000468991MTRNR2L12900
ENSP00000441600CCR3900
ENSP00000397181RGS4900
ENSP00000394624OPRM1900
ENSP00000387281ADRA2B900
ENSP00000373169DRD3900
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000378492GRM2900
ENSP00000379110CXCL1900
ENSP00000379140CXCL12900
ENSP00000381339GNAT3900
ENSP00000384665LPAR2900
ENSP00000386069ADRA2C900
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14900
ENSP00000386884CXCR4900
ENSP00000343428GPR18900
ENSP00000343027GNAI1900
ENSP00000351671CCL20900
ENSP00000342560HRH3900
ENSP00000298440OXGR1900
ENSP00000299727GALR1900
ENSP00000302079C3AR1900
ENSP00000302707FPR1900
ENSP00000302811MTNR1A900
ENSP00000304414CXCR6900
ENSP00000305416S1PR1900
ENSP00000305464APLN900
ENSP00000305651CXCL10900
ENSP00000297469GPER1900
ENSP00000305877NMUR1900
ENSP00000306884CXCL11900
ENSP00000307259P2RY12900
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E900
ENSP00000308361P2RY14900
ENSP00000342952ADCY2900
ENSP00000308815CCL19900
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000306512IL8900
ENSP00000297323ADCY1900
ENSP00000297313RGS20900
ENSP00000296140CCR1900
ENSP00000272644GPR17900
ENSP00000272928ACKR3900
ENSP00000280155ADRA2A900
ENSP00000281806MCHR2900
ENSP00000284981APP900
ENSP00000286355ADCY8900
ENSP00000286758CXCL13900
ENSP00000287641SST900
ENSP00000287907HTR5A900
ENSP00000292174CXCR5900
ENSP00000292301CCR2900
ENSP00000292303CCR5900
ENSP00000293272CCL5900
ENSP00000293275CCL16900
ENSP00000293778CXCL16900
ENSP00000293897SSTR5900
ENSP00000294016ADCY9900
ENSP00000295683CXCR1900
ENSP00000296026CXCL3900
ENSP00000296027CXCL5900
ENSP00000296028PPBP900
ENSP00000312999GNAI2900
ENSP00000313661HTR1D900
ENSP00000308549ADORA1900
ENSP00000319635CXCR2900
ENSP00000316244HTR1A900
ENSP00000332225PMCH900
ENSP00000332504CCR10900
ENSP00000332591NPY2R900
ENSP00000332659CCR4900
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000334050TAS2R42900
ENSP00000334448GNG2900
ENSP00000336764OPRL1900
ENSP00000339377NPY5R900
ENSP00000339393CCR6900
ENSP00000340191FPR2900
ENSP00000341821FPR3900
ENSP00000330138SSTR3900
ENSP00000330070NPW900
ENSP00000330284NPBWR1900
ENSP00000328708RXFP3900
ENSP00000327724TAS2R60900
ENSP00000326432CCR8900
ENSP00000324248PENK900
ENSP00000322924HTR1F900
ENSP00000327875LPAR5900
ENSP00000329684GALR2900
ENSP00000320376P2RY13900
ENSP00000319984CHRM2900
ENSP00000328472S1PR5900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.