IMPPAT Phytochemical information: 
Siamine

Siamine
Summary

SMILES: Oc1cc(O)c2c(c1)cc([nH]c2=O)C
InChI: InChI=1S/C10H9NO3/c1-5-2-6-3-7(12)4-8(13)9(6)10(14)11-5/h2-4,12-13H,1H3,(H,11,14)
InChIKey: RDYSDCWZHHUGIB-UHFFFAOYSA-N
DeepSMILES: OcccO)ccc6)cc[nH]c6=O)))C
Scaffold Graph/Node/Bond level: O=c1[nH]ccc2ccccc12
Scaffold Graph/Node level: OC1NCCC2CCCCC21
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cO; c[nH]c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Isoquinolones and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids
Synonymous chemical names:
Siamine, siamine
External chemical identifiers:
CID:CID_5359163; FDASRS:O0P6RV2UTU; SureChEMBL:SCHEMBL4955161
Chemical structure download


Siamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 191.19
Log P RDKit 1.25
Topological polar surface area (Å2) RDKit 73.32
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 4
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 9
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Siamine
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 0.59


Siamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No