IMPPAT Phytochemical information: 
Atherospermidine

Atherospermidine
Summary

SMILES: COc1c2OCOc2c2-c3ccccc3C(=O)c3c2c1ccn3
InChI: InChI=1S/C18H11NO4/c1-21-16-11-6-7-19-14-12(11)13(17-18(16)23-8-22-17)9-4-2-3-5-10(9)15(14)20/h2-7H,8H2,1H3
InChIKey: MDFFNDBAEOHIDY-UHFFFAOYSA-N
DeepSMILES: COccOCOc5c-cccccc6C=O)cc%10c%17ccn6
Scaffold Graph/Node/Bond level: O=C1c2ccccc2-c2c3c(cc4ccnc1c24)OCO3
Scaffold Graph/Node level: OC1C2CCCCC2C2C3OCOC3CC3CCNC1C32
Scaffold Graph level: CC1C2CCCCC2C2C3CCCC3CC3CCCC1C32
Functional groups: cOC; c1cOCO1; cC(=O)c; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
atherospermidine
External chemical identifiers:
CID:CID_77514; ChEBI:CHEBI:28780; FDASRS:E21QMO70E2; SureChEMBL:SCHEMBL6690046
Chemical structure download


Atherospermidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 305.29
Log P RDKit 3.18
Topological polar surface area (Å2) RDKit 57.65
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
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 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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


Atherospermidine
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 0.540371


Atherospermidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.78
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes