IMPPAT Phytochemical information: 
Crinasiatine

Crinasiatine
Summary

SMILES: Oc1ccc(cc1)CC1COc2c(O1)cc1c(c2)c2ccccc2[nH]c1=O
InChI: InChI=1S/C22H17NO4/c24-14-7-5-13(6-8-14)9-15-12-26-20-10-17-16-3-1-2-4-19(16)23-22(25)18(17)11-21(20)27-15/h1-8,10-11,15,24H,9,12H2,(H,23,25)
InChIKey: XFYYJHYSDXQMAE-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCCOccO6)cccc6)cccccc6[nH]c%10=O
Scaffold Graph/Node/Bond level: O=c1[nH]c2ccccc2c2cc3c(cc12)OC(Cc1ccccc1)CO3
Scaffold Graph/Node level: OC1NC2CCCCC2C2CC3OCC(CC4CCCCC4)OC3CC12
Scaffold Graph level: CC1CC2CCCCC2C2CC3CCC(CC4CCCCC4)CC3CC12
Functional groups: cO; cOC; c[nH]c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
crinasiatine, crinasiatine (phenanthridone)
External chemical identifiers:
CID:CID_442851; ChEBI:CHEBI:3916
Chemical structure download


Crinasiatine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 359.38
Log P RDKit 3.77
Topological polar surface area (Å2) RDKit 71.55
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
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


Crinasiatine
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 0.534608


Crinasiatine
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 -5.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes