IMPPAT Phytochemical information: 
alpha-Caesalpin
alpha-Caesalpin
Summary

SMILES: CC(=O)O[C@@H]1[C@@H]2[C@H](Cc3c([C@@]2(C)O)cco3)[C@@]2([C@]([C@H]1OC(=O)C)(O)C(C)(C)CCC2=O)C
InChI: InChI=1S/C24H32O8/c1-12(25)31-19-18-15(11-16-14(8-10-30-16)23(18,6)28)22(5)17(27)7-9-21(3,4)24(22,29)20(19)32-13(2)26/h8,10,15,18-20,28-29H,7,9,11H2,1-6H3/t15-,18-,19+,20-,22-,23+,24+/m0/s1
InChIKey: MESLDFVKOWKXTR-CUFXUFNESA-N
DeepSMILES: CC=O)O[C@@H][C@@H][C@H]Ccc[C@@]6C)O))cco5))))))[C@@][C@][C@H]6OC=O)C))))O)CC)C)CCC6=O))))))C
Scaffold Graph/Node/Bond level: O=C1CCCC2CCC3Cc4ccoc4CC3C12
Scaffold Graph/Node level: OC1CCCC2CCC3CC4CCOC4CC3C12
Scaffold Graph level: CC1CCCC2CCC3CC4CCCC4CC3C12
Functional groups: CC(=O)OC; CO; coc; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Cassane diterpenoids
Synonymous chemical names:
alpha caesalpin, alpha-caesalpin
External chemical identifiers:
CID:CID_21679154; ChEMBL:CHEMBL252323; ZINC:ZINC000028970193
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
alpha-Caesalpin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.51
Log P RDKit 2.28
Topological polar surface area (Å2) RDKit 123.27
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
alpha-Caesalpin
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 0.660773
alpha-Caesalpin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -8.19
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 Yes
P-glycoprotein substrate SwissADME Yes