IMPPAT Phytochemical information: 
Dehydrocarpaine I

Dehydrocarpaine I
Summary

SMILES: O=C1CCCCCCCC2CCC(C(=N2)C)OC(=O)CCCCCCCC2CCC(O1)C(C)N2
InChI: InChI=1S/C28H48N2O4/c1-21-25-19-17-23(29-21)13-9-5-3-8-12-16-28(32)34-26-20-18-24(30-22(26)2)14-10-6-4-7-11-15-27(31)33-25/h21,23-26,29H,3-20H2,1-2H3
InChIKey: KGQYREIAHMZYSA-UHFFFAOYSA-N
DeepSMILES: O=CCCCCCCCCCCCC=N6)C))OC=O)CCCCCCCCCCCO%26)CC)N6
Scaffold Graph/Node/Bond level: O=C1CCCCCCCC2CCC(CN2)OC(=O)CCCCCCCC2CCC(C=N2)O1
Scaffold Graph/Node level: OC1CCCCCCCC2CCC(CN2)OC(O)CCCCCCCC2CCC(CN2)O1
Scaffold Graph level: CC1CCCCCCCC2CCC(CC2)CC(C)CCCCCCCC2CCC(CC2)C1
Functional groups: COC(=O)C; CNC; CN=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
dehydrocarpaine i, Dehydrocarpaine I
External chemical identifiers:
CID:CID_131750991; ChEBI:CHEBI:172704
Chemical structure download


Dehydrocarpaine I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 476.7
Log P RDKit 6.05
Topological polar surface area (Å2) RDKit 76.99
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.89
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Dehydrocarpaine I
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.43


Dehydrocarpaine I
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.97
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes