IMPPAT Phytochemical information: 
(-)-8-Oxotetrahydropalmatine
(-)-8-Oxotetrahydropalmatine
Summary

SMILES: Oc1cc2CCN3C(c2cc1O)Cc1c(C3=O)c(O)c(cc1)O
InChI: InChI=1S/C17H15NO5/c19-12-2-1-9-5-11-10-7-14(21)13(20)6-8(10)3-4-18(11)17(23)15(9)16(12)22/h1-2,6-7,11,19-22H,3-5H2
InChIKey: WEDCJRJAWKSVRD-UHFFFAOYSA-N
DeepSMILES: OcccCCNCc6cc%10O))))CccC6=O))cO)ccc6))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2CC2c3ccccc3CCN12
Scaffold Graph/Node level: OC1C2CCCCC2CC2C3CCCCC3CCN12
Scaffold Graph level: CC1C2CCCCC2CC2C3CCCCC3CCC12
Functional groups: cO; cC(=O)N(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
(-)8-oxotetrahydropalmatine, (-)-8-oxotetrahydropalmatine, 8-oxotetrahydropalmatine
External chemical identifiers:
CID:CID_49769861
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(-)-8-Oxotetrahydropalmatine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 313.31
Log P RDKit 1.8
Topological polar surface area (Å2) RDKit 101.23
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
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 13
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
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
(-)-8-Oxotetrahydropalmatine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.555669
(-)-8-Oxotetrahydropalmatine
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 -6.71
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes