IMPPAT Phytochemical information: 
Crotananine

Crotananine
Summary

SMILES: CC1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)C(C(C1C)C)O
InChI: InChI=1S/C17H25NO5/c1-9-10(2)15(19)17(21)22-8-12-4-6-18-7-5-13(14(12)18)23-16(20)11(9)3/h4,9-11,13-15,19H,5-8H2,1-3H3/t9?,10?,11?,13-,14-,15?/m1/s1
InChIKey: GFXWTYYPYYHXDK-GLDVEYQJSA-N
DeepSMILES: CCC=O)O[C@@H]CCN[C@@H]5C=CC5))COC=O)CCC%15C))C))O
Scaffold Graph/Node/Bond level: O=C1CCCCC(=O)OC2CCN3CC=C(CO1)C23
Scaffold Graph/Node level: OC1CCCCC(O)OC2CCN3CCC(CO1)C23
Scaffold Graph level: CC1CCCCC(C)CC2CCC3CCC(CC1)C32
Functional groups: CC(=O)OC; CN(C)C; CC=C(C)C; COC(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
crotananine
External chemical identifiers:
CID:CID_156169; MolPort-046-153-838
Chemical structure download


Crotananine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 323.39
Log P RDKit 0.74
Topological polar surface area (Å2) RDKit 76.07
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3


Crotananine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.523326


Crotananine
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 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 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No