IMPPAT Phytochemical information: 
Deserpidine

Deserpidine
Summary

SMILES: COC(=O)[C@@H]1[C@@H](OC)[C@@H](C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c1[nH]c1c2cccc1)OC(=O)c1cc(OC)c(c(c1)OC)OC
InChI: InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
InChIKey: CVBMAZKKCSYWQR-WCGOZPBSSA-N
DeepSMILES: COC=O)[C@@H][C@@H]OC))[C@@H]C[C@H][C@@H]6C[C@H]NC6)CCcc6[nH]cc5cccc6)))))))))))))))))OC=O)cccOC))ccc6)OC)))OC
Scaffold Graph/Node/Bond level: O=C(OC1CCC2CC3c4[nH]c5ccccc5c4CCN3CC2C1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CCC2CC3C4NC5CCCCC5C4CCN3CC2C1)C1CCCCC1
Scaffold Graph level: CC(CC1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1)C1CCCCC1
Functional groups: COC(C)=O; cOC; COC; CN(C)C; c[nH]c; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
deserpidine, canescine
External chemical identifiers:
CID:CID_8550; ChEMBL:CHEMBL1200515; ChEBI:CHEBI:27478; ZINC:ZINC000004097186; FDASRS:9016E3VB47; SureChEMBL:SCHEMBL259343; MolPort-006-110-868
Chemical structure download


Deserpidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 578.66
Log P RDKit 4.16
Topological polar surface area (Å2) RDKit 108.55
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Deserpidine
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 0.41


Deserpidine
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 -6.92
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Deserpidine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000290866ACE800
ENSP00000298472SLC18A2800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.