IMPPAT Phytochemical information: 
Unii-72U0C7paav
Unii-72U0C7paav
Summary

SMILES: COc1ccc2c3c1Oc1c(O)c(OC)ccc1C1=C3N(CC2)[C@@]2(C1=O)C[C@H]1[C@]34[C@@H]2Oc2c4c(C[C@@H]1N(CC3)C)ccc2OC
InChI: InChI=1S/C36H34N2O7/c1-37-14-12-35-20-16-36(34(35)45-32-24(43-4)9-6-18(27(32)35)15-21(20)37)33(40)26-19-7-10-22(41-2)29(39)30(19)44-31-23(42-3)8-5-17-11-13-38(36)28(26)25(17)31/h5-10,20-21,34,39H,11-16H2,1-4H3/t20-,21+,34+,35-,36-/m1/s1
InChIKey: XWPPHGONALRWBY-IQXPYEGDSA-N
DeepSMILES: COcccccc6OccO)cOC))ccc6C=C%11NCC%15))[C@@]C5=O))C[C@H][C@@][C@@H]5Occ5cC[C@@H]9NCC%11))C))))ccc6OC
Scaffold Graph/Node/Bond level: O=C1C2=C3c4c(cccc4Oc4ccccc42)CCN3C12CC1C3Cc4cccc5c4C1(CCN3)C2O5
Scaffold Graph/Node level: OC1C2C3CCCCC3OC3CCCC4CCN(C2C43)C12CC1C3CC4CCCC5OC2C1(CCN3)C45
Scaffold Graph level: CC1C2C3CCCCC3CC3CCCC4CCC(C2C43)C12CC1C3CCCC14C1C(CCCC1CC24)C3
Functional groups: CN(C)C; cC1=C(c)N(C)CC1=O; cO; cOC; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxepines
ClassyFire Subclass: Dibenzoxepines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Morphinan alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
cancentrine
External chemical identifiers:
CID:101588305; ZINC:ZINC000085881344; FDASRS:72U0C7PAAV
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Unii-72U0C7paav
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 606.68
Log P RDKit 4.55
Topological polar surface area (Å2) RDKit 89.93
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Unii-72U0C7paav
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4614
Unii-72U0C7paav
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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