IMPPAT Phytochemical information: 
Caranine
Caranine
Summary

SMILES: O[C@@H]1CC=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
InChI: InChI=1S/C16H17NO3/c18-12-2-1-9-3-4-17-7-10-5-13-14(20-8-19-13)6-11(10)15(12)16(9)17/h1,5-6,12,15-16,18H,2-4,7-8H2/t12-,15-,16-/m1/s1
InChIKey: XKYSLILSDJBMCU-DAXOMENPSA-N
DeepSMILES: O[C@@H]CC=C[C@@H][C@@H]6cccOCOc5cc9CN%13CC%16
Scaffold Graph/Node/Bond level: C1=C2CCN3Cc4cc5c(cc4C(CC1)C23)OCO5
Scaffold Graph/Node level: C1CC2CCN3CC4CC5OCOC5CC4C(C1)C23
Scaffold Graph level: C1CC2CC3CC4CCC5CCCC(C3CC2C1)C54
Functional groups: CO; CC=C(C)C; c1cOCO1; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Lycorine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids|Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids|Indolizidine alkaloids
Synonymous chemical names:
caranine
External chemical identifiers:
CID:CID_441589; ChEMBL:CHEMBL575125; ChEBI:CHEBI:3383; ZINC:ZINC000004097642; SureChEMBL:SCHEMBL21578195
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Caranine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 271.32
Log P RDKit 1.78
Topological polar surface area (Å2) RDKit 41.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Caranine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.730356
Caranine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.18
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes