IMPPAT Phytochemical information: 
Aricine

Aricine
Summary

SMILES: COc1ccc2c(c1)c1CCN3[C@H](c1[nH]2)C[C@H]1[C@@H](C3)[C@H](C)OC=C1C(=O)OC
InChI: InChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-14-16-8-13(26-2)4-5-19(16)23-21(14)20(24)9-15(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,15,17,20,23H,6-7,9-10H2,1-3H3/t12-,15-,17-,20-/m0/s1
InChIKey: DTDADHMBRZKXSC-GKASHWOUSA-N
DeepSMILES: COcccccc6)cCCN[C@H]c6[nH]9))C[C@H][C@@H]C6)[C@H]C)OC=C6C=O)OC
Scaffold Graph/Node/Bond level: C1=CC2CC3c4[nH]c5ccccc5c4CCN3CC2CO1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3COCCC3CC12
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: cOC; CN(C)C; c[nH]c; COC(=O)C(=COC)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type|Yohimbine-like alkaloids
Synonymous chemical names:
aricine, heterophylline
External chemical identifiers:
CID:CID_251575; ChEMBL:CHEMBL525626; ChEBI:CHEBI:2821; ZINC:ZINC000053201251; FDASRS:BUW4ULQ00A; SureChEMBL:SCHEMBL17089219; MolPort-039-052-471
Chemical structure download


Aricine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.46
Log P RDKit 3.19
Topological polar surface area (Å2) RDKit 63.79
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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


Aricine
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 0.808503


Aricine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.70
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No