IMPPAT Phytochemical information: 
N-[1-[(13E)-10-butan-2-yl-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.2.2.03,7]nonadeca-1(17),13,15,18-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-2-(dimethylamino)-3-phenylpropanamide
N-[1-[(13E)-10-butan-2-yl-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.2.2.03,7]nonadeca-1(17),13,15,18-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-2-(dimethylamino)-3-phenylpropanamide
Summary

SMILES: CCC(C(C(=O)N1CCC2C1C(=O)NC(C(CC)C)C(=O)N/C=C\c1ccc(O2)cc1)NC(=O)C(N(C)C)Cc1ccccc1)C
InChI: InChI=1S/C36H49N5O5/c1-7-23(3)30-34(43)37-20-18-25-14-16-27(17-15-25)46-29-19-21-41(32(29)35(44)38-30)36(45)31(24(4)8-2)39-33(42)28(40(5)6)22-26-12-10-9-11-13-26/h9-18,20,23-24,28-32H,7-8,19,21-22H2,1-6H3,(H,37,43)(H,38,44)(H,39,42)/b20-18-
InChIKey: VNEXXKFUERBRNG-ZZEZOPTASA-N
DeepSMILES: CCCCC=O)NCCCC5C=O)NCCCC))C))C=O)N/C=C\ccccO%14)cc6)))))))))))))))))))NC=O)CNC)C))Ccccccc6)))))))))))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)C2C(CCN2C(=O)CNC(=O)CCc2ccccc2)Oc2ccc(cc2)C=CN1
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCC(O)N1CCC2OC3CCC(CCNC(O)CNC(O)C21)CC3
Scaffold Graph level: CC(CCC1CCCCC1)CCC(C)C1CCC2CC3CCC(CCCC(C)CCC(C)C21)CC3
Functional groups: CNC(C)=O; CN(C)C; CC(=O)N(C)C; CNC(=O)C; c/C=C\NC(=O)C; cOC
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:
amphibine d
External chemical identifiers:
CID:CID_12306074
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N-[1-[(13E)-10-butan-2-yl-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.2.2.03,7]nonadeca-1(17),13,15,18-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-2-(dimethylamino)-3-phenylpropanamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 631.82
Log P RDKit 3.37
Topological polar surface area (Å2) RDKit 120.08
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 8
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
N-[1-[(13E)-10-butan-2-yl-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.2.2.03,7]nonadeca-1(17),13,15,18-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-2-(dimethylamino)-3-phenylpropanamide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
N-[1-[(13E)-10-butan-2-yl-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.2.2.03,7]nonadeca-1(17),13,15,18-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-2-(dimethylamino)-3-phenylpropanamide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -6.39
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