IMPPAT Phytochemical information: 
Auricularine

Auricularine
Summary

SMILES: CN(CCc1c2ccccc2[nH]c1[C@@H]1[C@@H]2[C@@H]([C@@]34[C@]1(CCN4C)c1ccccc1N3)C=C(CC2(C)C)C)C
InChI: InChI=1S/C33H42N4/c1-21-19-25-28(31(2,3)20-21)29(30-23(15-17-36(4)5)22-11-7-9-13-26(22)34-30)32-16-18-37(6)33(25,32)35-27-14-10-8-12-24(27)32/h7-14,19,25,28-29,34-35H,15-18,20H2,1-6H3/t25-,28-,29-,32+,33+/m0/s1
InChIKey: RTHNIWHULJBNTJ-BXFVMDGOSA-N
DeepSMILES: CNCCccccccc6[nH]c9[C@@H][C@@H][C@@H][C@][C@]5CCN5C))))cccccc6N9)))))))))C=CCC6C)C)))C)))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2C(CC1)C(c1cc3ccccc3[nH]1)C13CCNC21Nc1ccccc13
Scaffold Graph/Node level: C1CCC2NC(C3C4CCCCC4C45NCCC34C3CCCCC3N5)CC2C1
Scaffold Graph level: C1CCC2CC(C3C4CCCCC4C45CCCC34C3CCCCC3C5)CC2C1
Functional groups: CN(C)C; c[nH]c; cN[C@@](C)(C)N(C)C; CC(C)=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyrroloindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
auricularine
External chemical identifiers:
CID:CID_441990; ChEMBL:CHEMBL4165417; ChEBI:CHEBI:2927; ZINC:ZINC000004097861
Chemical structure download


Auricularine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 494.73
Log P RDKit 6.37
Topological polar surface area (Å2) RDKit 34.3
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Auricularine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41


Auricularine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.93
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 No