IMPPAT Phytochemical information: 
Dehydrobufotenine

Dehydrobufotenine
Summary

SMILES: Oc1ccc2c3c1[N+](C)(C)CCc3c[nH]2
InChI: InChI=1S/C12H14N2O/c1-14(2)6-5-8-7-13-9-3-4-10(15)12(14)11(8)9/h3-4,7,13H,5-6H2,1-2H3/p+1
InChIKey: XRZDSPVDZKCARG-UHFFFAOYSA-O
DeepSMILES: Occcccc6[N+]C)C)CCc6c[nH]9
Scaffold Graph/Node/Bond level: c1cc2c3c(c[nH]c3c1)CC[NH2+]2
Scaffold Graph/Node level: C1CC2NCCC3CNC(C1)C32
Scaffold Graph level: C1CC2CCCC3CCC(C1)C23
Functional groups: cO; c[nH]c; c[N+](C)(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Pyrroloquinolines
Synonymous chemical names:
dehydrobufotenine
External chemical identifiers:
CID:CID_205042
Chemical structure download


Dehydrobufotenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 203.27
Log P RDKit 2
Topological polar surface area (Å2) RDKit 36.02
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Dehydrobufotenine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63


Dehydrobufotenine
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 -6.38
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 Yes