IMPPAT Phytochemical information: 
Echitoserpine
Echitoserpine
Summary

SMILES: COc1ccc2c(c1)NC1=C(C[C@]3([C@H]4[C@@]21CCN4CCC3)[C@H](OC(=O)c1cc(OC)c2c(c1)OCO2)C)C(=O)OC
InChI: InChI=1S/C31H34N2O8/c1-17(41-27(34)18-12-23(37-3)25-24(13-18)39-16-40-25)30-8-5-10-33-11-9-31(29(30)33)21-7-6-19(36-2)14-22(21)32-26(31)20(15-30)28(35)38-4/h6-7,12-14,17,29,32H,5,8-11,15-16H2,1-4H3/t17-,29+,30+,31+/m1/s1
InChIKey: ZVLITPGUZVSYOS-OOBHTYFASA-N
DeepSMILES: COcccccc6)NC=CC[C@][C@H][C@@]96CCN5CCC9))))))))[C@H]OC=O)cccOC))ccc6)OCO5))))))))))C))))C=O)OC
Scaffold Graph/Node/Bond level: O=C(OCC12CC=C3Nc4ccccc4C34CCN(CCC1)C24)c1ccc2c(c1)OCO2
Scaffold Graph/Node level: OC(OCC12CCCN3CCC4(C(CC1)NC1CCCCC14)C32)C1CCC2OCOC2C1
Scaffold Graph level: CC(CCC12CCCC3CCC4(C(CC1)CC1CCCCC14)C32)C1CCC2CCCC2C1
Functional groups: cOC; c1cOCO1; cNC(=C(C(=O)OC)C)C; CN(C)C; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidospermatan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
echitoserpine, Echitoserpine
External chemical identifiers:
CID:CID_102117082
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Echitoserpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.62
Log P RDKit 4.03
Topological polar surface area (Å2) RDKit 104.79
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Echitoserpine
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 0.52
Echitoserpine
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 -6.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes