IMPPAT Phytochemical information: 
Serpentinine
Serpentinine
Summary

SMILES: COC(=O)C(C1CC2N(C/C/1=C\C)CCc1c2[nH]c2c1cccc2)Cc1c[n+]2CC3C(C)OC=C(C3Cc2c2c1c1ccccc1[nH]2)C(=O)OC
InChI: InChI=1S/C42H44N4O5/c1-5-24-19-45-15-14-27-26-10-6-8-12-34(26)43-39(27)36(45)17-29(24)31(41(47)49-3)16-25-20-46-21-32-23(2)51-22-33(42(48)50-4)30(32)18-37(46)40-38(25)28-11-7-9-13-35(28)44-40/h5-13,20,22-23,29-32,36,43H,14-19,21H2,1-4H3/p+1/b24-5+
InChIKey: QWAUBSSAJRGKPX-ZXKDJJQISA-O
DeepSMILES: COC=O)CCCCNC/C/6=C\C))))CCcc6[nH]cc5cccc6)))))))))))))))Ccc[n+]CCCC)OC=CC6Cc%10cc%14cccccc6[nH]9))))))))))))C=O)OC
Scaffold Graph/Node/Bond level: C=C1CN2CCc3c([nH]c4ccccc34)C2CC1CCc1c[n+]2c(c3[nH]c4ccccc4c13)CC1C=COCC1C2
Scaffold Graph/Node level: CC1CN2CCC3C4CCCCC4NC3C2CC1CCC1CN2CC3COCCC3CC2C2NC3CCCCC3C12
Scaffold Graph level: CC1CC2CCC3C4CCCCC4CC3C2CC1CCC1CC2CC3CCCCC3CC2C2CC3CCCCC3C12
Functional groups: COC=C(C(=O)OC)C; COC(C)=O; CN(C)C; C/C=C(/C)C; c[nH]c; c[n+](c)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
Synonymous chemical names:
Serpentinine, serpentinine
External chemical identifiers:
CID:CID_5351576
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Serpentinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 685.85
Log P RDKit 6.25
Topological polar surface area (Å2) RDKit 100.53
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 42
Number of heavy atoms RDKit 51
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 25
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 3
Number of aromatic rings RDKit 5
Total number of rings RDKit 9
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 9
Serpentinine
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 0.128973
Serpentinine
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 -6.48
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes