IMPPAT Phytochemical information: 
Malabarolide

Malabarolide
Summary

SMILES: O[C@@H]1C[C@H](O)C2[C@H]([C@@H]1O)C1(C)C[C@@H](OC(=O)C1(CC2)O)c1cocc1
InChI: InChI=1S/C18H24O7/c1-17-7-13(9-3-5-24-8-9)25-16(22)18(17,23)4-2-10-11(19)6-12(20)15(21)14(10)17/h3,5,8,10-15,19-21,23H,2,4,6-7H2,1H3/t10?,11-,12+,13+,14+,15+,17?,18?/m0/s1
InChIKey: ZINGMSLHDAUDDW-YVHDXGIRSA-N
DeepSMILES: O[C@@H]C[C@H]O)C[C@H][C@@H]6O))CC)C[C@@H]OC=O)C6CC%10))O))))ccocc5
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)CC2C1CCC1CCCCC12
Scaffold Graph/Node level: OC1OC(C2CCOC2)CC2C3CCCCC3CCC12
Scaffold Graph level: CC1CC(C2CCCC2)CC2C1CCC1CCCCC12
Functional groups: CO; CC(=O)OC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
ClassyFire Subclass: Naphthopyranones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
malabarolide
External chemical identifiers:
CID:CID_362487
Chemical structure download


Malabarolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.38
Log P RDKit 0.52
Topological polar surface area (Å2) RDKit 120.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.72
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Malabarolide
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 0.543793


Malabarolide
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 -8.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes