IMPPAT Phytochemical information: 
Lysergene

Lysergene
Summary

SMILES: C=C1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3
InChI: InChI=1S/C16H16N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,15,17H,1,7,9H2,2H3/t15-/m1/s1
InChIKey: MVCNPXUMKZNDRO-OAHLLOKOSA-N
DeepSMILES: C=CCNC)[C@H]C=C6)cccccc6cC%10)c[nH]5
Scaffold Graph/Node/Bond level: C=C1C=C2c3cccc4[nH]cc(c34)CC2NC1
Scaffold Graph/Node level: CC1CNC2CC3CNC4CCCC(C2C1)C34
Scaffold Graph level: CC1CCC2CC3CCC4CCCC(C2C1)C43
Functional groups: cC(=CC(=C)C)C; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Indoloquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Ergot alkaloids
Synonymous chemical names:
Lysergene, lysergene
External chemical identifiers:
CID:CID_12312578; ChEMBL:CHEMBL39604; ZINC:ZINC000014583981; FDASRS:553QH53YND; SureChEMBL:SCHEMBL7640520
Chemical structure download


Lysergene
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 236.32
Log P RDKit 2.98
Topological polar surface area (Å2) RDKit 19.03
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Lysergene
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 0.74


Lysergene
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 -5.63
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 No
P-glycoprotein substrate SwissADME Yes