IMPPAT Phytochemical information: 
Caesalpinine A
Caesalpinine A
Summary

SMILES: O=C1NC[C@H]2CN(C(=O)[C@H]2[C@@H](c2ccccc2)O)CCCCN[C@H](C1)c1ccccc1
InChI: InChI=1S/C25H31N3O3/c29-22-15-21(18-9-3-1-4-10-18)26-13-7-8-14-28-17-20(16-27-22)23(25(28)31)24(30)19-11-5-2-6-12-19/h1-6,9-12,20-21,23-24,26,30H,7-8,13-17H2,(H,27,29)/t20-,21+,23+,24+/m0/s1
InChIKey: SHBCCFGHZDXOET-XWVZOOPGSA-N
DeepSMILES: O=CNC[C@H]CNC=O)[C@H]5[C@@H]cccccc6))))))O))))CCCCN[C@H]C%13)cccccc6
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)NCCCCN2CC(CN1)C(Cc1ccccc1)C2=O
Scaffold Graph/Node level: OC1CC(C2CCCCC2)NCCCCN2CC(CN1)C(CC1CCCCC1)C2O
Scaffold Graph level: CC1CCC2CC(CCCCCC(C3CCCCC3)C1)C(C)C2CC1CCCCC1
Functional groups: CN(C)C(C)=O; CNC; CNC(C)=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Peptidomimetics
ClassyFire Subclass: Hybrid peptides
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
caesalpinine a
External chemical identifiers:
CID:5458904
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Caesalpinine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 421.54
Log P RDKit 2.43
Topological polar surface area (Å2) RDKit 81.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Caesalpinine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7111
Caesalpinine A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -7.49
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes