IMPPAT Phytochemical information: 
(2S)-2-methyl-4-[(2R,10R,13R)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxypentadec-4-enyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
(2S)-2-methyl-4-[(2R,10R,13R)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxypentadec-4-enyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Summary

SMILES: CCCCCCCCCC/C=C\CC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CC[C@@H](CCCCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O
InChI: InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(40)35-25-26-36(44-35)34(41)24-23-31(38)20-17-14-13-15-18-21-32(39)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12-/t29-,31+,32+,33+,34+,35+,36+/m0/s1
InChIKey: XHKLAUPULLMCQU-WGNRZNTBSA-N
DeepSMILES: CCCCCCCCCC/C=C\CC[C@H][C@H]CC[C@@H]O5)[C@@H]CC[C@@H]CCCCCCC[C@H]CC=C[C@@H]OC5=O)))C)))))O)))))))))O))))O))))))O
Scaffold Graph/Node/Bond level: O=C1OCC=C1CCCCCCCCCCCCCC1CCCO1
Scaffold Graph/Node level: OC1OCCC1CCCCCCCCCCCCCC1CCCO1
Scaffold Graph level: CC1CCCC1CCCCCCCCCCCCCC1CCCC1
Functional groups: CC1=CCOC1=O; CO; C/C=C\C; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty alcohols
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Linear polyketides
NP Classifier Class: Acetogenins
Synonymous chemical names:
squamosten a, Squamosten A
External chemical identifiers:
CID:CID_102153564
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-2-methyl-4-[(2R,10R,13R)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxypentadec-4-enyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 622.93
Log P RDKit 7.62
Topological polar surface area (Å2) RDKit 116.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 27
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
(2S)-2-methyl-4-[(2R,10R,13R)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxypentadec-4-enyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0423064
(2S)-2-methyl-4-[(2R,10R,13R)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(Z,1R)-1-hydroxypentadec-4-enyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
ADME 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -3.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No