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: CNC(=O)C; CN(C)C(=O)C; CO; CNC
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: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 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.71
Caesalpinine A
ADME 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
Number of Brenk structural alerts SwissADME 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