IMPPAT Phytochemical information: 
Serotobenine
Serotobenine
Summary

SMILES: COc1cc(ccc1O)[C@H]1Oc2c3[C@@H]1C(=O)NCCc1c3c(cc2)[nH]c1
InChI: InChI=1S/C20H18N2O4/c1-25-15-8-10(2-4-13(15)23)19-18-17-14(26-19)5-3-12-16(17)11(9-22-12)6-7-21-20(18)24/h2-5,8-9,18-19,22-23H,6-7H2,1H3,(H,21,24)/t18-,19+/m0/s1
InChIKey: GEJUXZYANAYHRZ-RBUKOAKNSA-N
DeepSMILES: COcccccc6O))))[C@H]Occ[C@@H]5C=O)NCCcc8ccc%12))[nH]c5
Scaffold Graph/Node/Bond level: O=C1NCCc2c[nH]c3ccc4c(c23)C1C(c1ccccc1)O4
Scaffold Graph/Node level: OC1NCCC2CNC3CCC4OC(C5CCCCC5)C1C4C23
Scaffold Graph level: CC1CCCC2CCC3CCC4CC(C5CCCCC5)C1C4C23
Functional groups: cOC; cO; CNC(=O)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
serotobenine (indole alkaloid), serotobenine
External chemical identifiers:
CID:CID_11725426; ZINC:ZINC000014696265
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Serotobenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 350.37
Log P RDKit 2.77
Topological polar surface area (Å2) RDKit 83.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Serotobenine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.663572
Serotobenine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes