IMPPAT Phytochemical information: 
Castanospermine
Castanospermine
Summary

SMILES: O[C@@H]1[C@@H](O)CN2[C@@H]([C@H]1O)[C@@H](O)CC2
InChI: InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
InChIKey: JDVVGAQPNNXQDW-TVNFTVLESA-N
DeepSMILES: O[C@@H][C@@H]O)CN[C@@H][C@H]6O))[C@@H]O)CC5
Scaffold Graph/Node/Bond level: C1CCN2CCCC2C1
Scaffold Graph/Node level: C1CCN2CCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Indolizidine alkaloids
Synonymous chemical names:
castanospermine
External chemical identifiers:
CID:CID_54445; ChEMBL:CHEMBL311226; ChEBI:CHEBI:27860; ZINC:ZINC000003775177; FDASRS:Q0I3184XM7; SureChEMBL:SCHEMBL61040; MolPort-003-845-673
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Castanospermine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 189.21
Log P RDKit -2.48
Topological polar surface area (Å2) RDKit 84.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.62
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2
Castanospermine
Drug-likeness
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.338914
Castanospermine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.04
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Castanospermine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001205ENSG00000151092NGLY155768ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL, NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_000567ENSG00000177628GBA12629ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001307ENSG00000070610GBA257704ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426NPASS