IMPPAT Phytochemical information: 
methyl (1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylate
methyl (1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylate
Summary

SMILES: COC(=O)[C@@H]1C[C@H](O)C[C@@H]2[C@@H]1[C@H]1OC(=O)[C@]3(C1)[C@@]2(C)C[C@@H](O3)c1cocc1
InChI: InChI=1S/C20H24O7/c1-19-7-14(10-3-4-25-9-10)27-20(19)8-15(26-18(20)23)16-12(17(22)24-2)5-11(21)6-13(16)19/h3-4,9,11-16,21H,5-8H2,1-2H3/t11-,12+,13+,14+,15-,16+,19-,20+/m0/s1
InChIKey: OPNWTAMLIMDKEY-UWGSWSTESA-N
DeepSMILES: COC=O)[C@@H]C[C@H]O)C[C@@H][C@@H]6[C@H]OC=O)[C@]C5)[C@@]7C)C[C@@H]O5)ccocc5
Scaffold Graph/Node/Bond level: O=C1OC2CC13OC(c1ccoc1)CC3C1CCCCC21
Scaffold Graph/Node level: OC1OC2CC13OC(C1CCOC1)CC3C1CCCCC21
Scaffold Graph level: CC1CC2CC13CC(C1CCCC1)CC3C1CCCCC21
Functional groups: COC(C)=O; CO; COC(=O)C; COC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
furanoid norditerpenes-diosbulbins a, diosbulbin-a, diosbulbin a
External chemical identifiers:
CID:CID_21723240; ZINC:ZINC000006032345
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 376.41
Log P RDKit 1.99
Topological polar surface area (Å2) RDKit 95.2
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
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 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
methyl (1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylate
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 0.788826
methyl (1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylate
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 -7.57
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 No
P-glycoprotein substrate SwissADME No