IMPPAT Phytochemical information: 
Borreverine

Borreverine
Summary

SMILES: CNCCc1c2ccccc2[nH]c1[C@@H]1[C@@H]2[C@@H]([C@@]34[C@]1(CCN4C)c1ccccc1N3)C=C(CC2(C)C)C
InChI: InChI=1S/C32H40N4/c1-20-18-24-27(30(2,3)19-20)28(29-22(14-16-33-4)21-10-6-8-12-25(21)34-29)31-15-17-36(5)32(24,31)35-26-13-9-7-11-23(26)31/h6-13,18,24,27-28,33-35H,14-17,19H2,1-5H3/t24-,27-,28-,31+,32+/m0/s1
InChIKey: PHMBUGRSZKDHNS-QGEDZZHQSA-N
DeepSMILES: CNCCccccccc6[nH]c9[C@@H][C@@H][C@@H][C@][C@]5CCN5C))))cccccc6N9)))))))))C=CCC6C)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: CNC; 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: Aspidosperma type
Synonymous chemical names:
borreverine
External chemical identifiers:
CID:CID_442020; ChEMBL:CHEMBL4163038; ChEBI:CHEBI:3156; ZINC:ZINC000004097888
Chemical structure download


Borreverine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 480.7
Log P RDKit 6.03
Topological polar surface area (Å2) RDKit 43.09
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 36
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 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.5
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


Borreverine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.399514


Borreverine
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 -5.18
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 No
P-glycoprotein substrate SwissADME No