IMPPAT Phytochemical information: 
angustilobine B, (rac)-

angustilobine B, (rac)-
Summary

SMILES: COC(=O)C12COCC=C3C1CCN(C3)Cc1c2[nH]c2c1cccc2
InChI: InChI=1S/C20H22N2O3/c1-24-19(23)20-12-25-9-7-13-10-22(8-6-16(13)20)11-15-14-4-2-3-5-17(14)21-18(15)20/h2-5,7,16,21H,6,8-12H2,1H3
InChIKey: IFPNVCKONQNHIZ-UHFFFAOYSA-N
DeepSMILES: COC=O)CCOCC=CC7CCNC6)Ccc%13[nH]cc5cccc6
Scaffold Graph/Node/Bond level: C1=C2CN3CCC2C(COC1)c1[nH]c2ccccc2c1C3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3COCCC4CN(CCC43)CC21
Scaffold Graph level: C1CCC2C3CCC(CC3C1)CC1C3CCCCC3CC21
Functional groups: COC(C)=O; COC; CC=C(C)C; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vallesaman alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
angustilobine b, angustilobine B
External chemical identifiers:
CID:CID_13891905; ChEBI:CHEBI:70511
Chemical structure download


angustilobine B, (rac)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.41
Log P RDKit 2.37
Topological polar surface area (Å2) RDKit 54.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6


angustilobine B, (rac)-
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 0.640653


angustilobine B, (rac)-
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 -7.54
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