IMPPAT Phytochemical information: 
Anacrotine
Anacrotine
Summary

SMILES: C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)[C@H](O)C3
InChI: InChI=1S/C18H25NO6/c1-4-11-7-10(2)18(3,23)17(22)24-9-12-5-6-19-8-13(20)15(14(12)19)25-16(11)21/h4-5,10,13-15,20,23H,6-9H2,1-3H3/b11-4-/t10-,13-,14-,15-,18-/m1/s1
InChIKey: NPYPUYCITBTPSF-TZCAYXSXSA-N
DeepSMILES: C/C=C/C[C@@H]C)[C@@]C)O)C=O)OCC=CCN[C@H]5[C@H]OC/%15=O)))[C@H]O)C5
Scaffold Graph/Node/Bond level: C=C1CCCC(=O)OCC2=CCN3CCC(OC1=O)C23
Scaffold Graph/Node level: CC1CCCC(O)OCC2CCN3CCC(OC1O)C23
Scaffold Graph level: CC1CCCC(C)C(C)CC2CCC3CCC(CC1)C32
Functional groups: C/C=C(/C)C(=O)OC; CO; COC(=O)C; CC=C(C)C; CN(C)C
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:
anacrotine, crotalaburnine
External chemical identifiers:
CID:CID_5281720; ChEBI:CHEBI:2697; ZINC:ZINC000004098635; MolPort-039-339-127
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Anacrotine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 351.4
Log P RDKit 0.16
Topological polar surface area (Å2) RDKit 96.3
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
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
Anacrotine
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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
Anacrotine
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 -8.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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