IMPPAT Phytochemical information: 
Neodiospyrin

Neodiospyrin
Summary

SMILES: Cc1cc(O)c2c(c1)C(=O)C=C(C2=O)c1c(C)cc(c2c1C(=O)C=CC2=O)O
InChI: InChI=1S/C22H14O6/c1-9-5-11-15(25)8-12(22(28)19(11)16(26)6-9)18-10(2)7-17(27)20-13(23)3-4-14(24)21(18)20/h3-8,26-27H,1-2H3
InChIKey: LZAXNDGRDVWTFX-UHFFFAOYSA-N
DeepSMILES: CcccO)ccc6)C=O)C=CC6=O))ccC)cccc6C=O)C=CC6=O)))))))O
Scaffold Graph/Node/Bond level: O=C1C=C(c2cccc3c2C(=O)C=CC3=O)C(=O)c2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCC3C(O)CCC(O)C32)C(O)C2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC3C(C)CCC(C)C32)C(C)C2CCCCC12
Functional groups: cO; cC1=CC(=O)ccC1=O; O=C1C=CC(=O)cc1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Bisnaphthalenes|Naphthoquinones
Synonymous chemical names:
neodiospyrin
External chemical identifiers:
CID:CID_16072922; ChEMBL:CHEMBL241392; ChEBI:CHEBI:172603
Chemical structure download


Neodiospyrin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.35
Log P RDKit 3.11
Topological polar surface area (Å2) RDKit 108.74
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
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 20
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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


Neodiospyrin
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 0.79


Neodiospyrin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.94
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No