IMPPAT Phytochemical information: 
Macrocarpamine
Macrocarpamine
Summary

SMILES: COC(=O)[C@@H]1[C@H]2C[C@H]3[C@]4(N1c1ccccc1[C@H]4CCN3C/C/2=C/C)/C=C/C1=COC[C@@H]2[C@H]1C[C@@H]1N([C@H]2Cc2c1n(C)c1c2cccc1)C
InChI: InChI=1S/C41H46N4O3/c1-5-24-21-44-17-15-32-27-11-7-9-13-34(27)45-39(40(46)47-4)29(24)20-37(44)41(32,45)16-14-25-22-48-23-31-28(25)18-36-38-30(19-35(31)42(36)2)26-10-6-8-12-33(26)43(38)3/h5-14,16,22,28-29,31-32,35-37,39H,15,17-21,23H2,1-4H3/b16-14+,24-5-/t28-,29-,31+,32+,35-,36-,37-,39-,41-/m0/s1
InChIKey: NOKYQXVIWFQLED-HXCLOJFDSA-N
DeepSMILES: COC=O)[C@@H][C@H]C[C@H][C@]N6cccccc6[C@H]9CCN%13C/C/%17=C/C)))))))))))))))/C=C/C=COC[C@@H][C@H]6C[C@@H]N[C@H]6Ccc6nC)cc5cccc6)))))))))))C
Scaffold Graph/Node/Bond level: C=C1CN2CCC3c4ccccc4N4CC1CC2C34C=CC1=COCC2C3Cc4c([nH]c5ccccc45)C(CC12)N3
Scaffold Graph/Node level: CC1CN2CCC3C4CCCCC4N4CC1CC2C34CCC1COCC2C3CC4C5CCCCC5NC4C(CC12)N3
Scaffold Graph level: CC1CC2CCC3C4CCCCC4C4CC1CC2C34CCC1CCCC2C3CC(CC12)C1CC2CCCCC2C1C3
Functional groups: COC(C)=O; CN(C)C; cn(C)c; cN(C)C; C/C=C(/C)C; COC=C(/C=C/C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Pleiocarpaman alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
macrocarpamine
External chemical identifiers:
CID:CID_5472477; ChEMBL:CHEMBL1979029; ZINC:ZINC000082175034
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Macrocarpamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 642.84
Log P RDKit 6.12
Topological polar surface area (Å2) RDKit 50.18
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 41
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.49
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 7
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Macrocarpamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.253651
Macrocarpamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly 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 -6.74
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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