IMPPAT Phytochemical information: 
(13Z)-10-butan-2-yl-6-[2-(dimethylamino)-3-(1H-indol-3-yl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraene-8,11-dione
(13Z)-10-butan-2-yl-6-[2-(dimethylamino)-3-(1H-indol-3-yl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraene-8,11-dione
Summary

SMILES: CCC(C1NC(=O)C2C(CCN2C(=O)C(N(C)C)Cc2c[nH]c3c2cccc3)Oc2cc(/C=C\NC1=O)c(OC)cc2)C
InChI: InChI=1S/C33H41N5O5/c1-6-20(2)29-31(39)34-15-13-21-17-23(11-12-27(21)42-5)43-28-14-16-38(30(28)32(40)36-29)33(41)26(37(3)4)18-22-19-35-25-10-8-7-9-24(22)25/h7-13,15,17,19-20,26,28-30,35H,6,14,16,18H2,1-5H3,(H,34,39)(H,36,40)/b15-13-
InChIKey: ZBSVQPVKCVFMBL-SQFISAMPSA-N
DeepSMILES: CCCCNC=O)CCCCN5C=O)CNC)C))Ccc[nH]cc5cccc6)))))))))))))))Occc/C=C\NC%13=O)))))cOC))cc6))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)C2C(CCN2C(=O)CCc2c[nH]c3ccccc23)Oc2cccc(c2)C=CN1
Scaffold Graph/Node level: OC1CNC(O)C2C(CCN2C(O)CCC2CNC3CCCCC23)OC2CCCC(CCN1)C2
Scaffold Graph level: CC1CCCC2CCCC(C2)CC2CCC(C(C)CCC3CCC4CCCCC43)C2C(C)CC1
Functional groups: c/C=C\NC(=O)C; CNC(=O)C; cOC; CC(=O)N(C)C; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids|Amino acids and Peptides
NP Classifier Superclass: Peptide alkaloids
NP Classifier Class: Ansa peptide alkaloids
Synonymous chemical names:
Nummularine R, nummularine r
External chemical identifiers:
CID:CID_101426140
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(13Z)-10-butan-2-yl-6-[2-(dimethylamino)-3-(1H-indol-3-yl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraene-8,11-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 587.72
Log P RDKit 3.33
Topological polar surface area (Å2) RDKit 116
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(13Z)-10-butan-2-yl-6-[2-(dimethylamino)-3-(1H-indol-3-yl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraene-8,11-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.390757
(13Z)-10-butan-2-yl-6-[2-(dimethylamino)-3-(1H-indol-3-yl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraene-8,11-dione
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.81
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 Yes
P-glycoprotein substrate SwissADME Yes