IMPPAT Phytochemical information: 
[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
Summary

SMILES: CC[C@@H](C(=O)O[C@H](C1=CC(=O)OC1)C[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1CCC[C@@]12CO1)COC(=O)C)OC(=O)C)C
InChI: InChI=1S/C29H42O9/c1-7-17(2)26(33)38-22(21-12-25(32)34-14-21)13-27(6)18(3)11-24(37-20(5)31)29(16-35-19(4)30)23(27)9-8-10-28(29)15-36-28/h12,17-18,22-24H,7-11,13-16H2,1-6H3/t17-,18+,22-,23+,24-,27-,28-,29-/m0/s1
InChIKey: LJHYCABROUGORR-DUWLCKCXSA-N
DeepSMILES: CC[C@@H]C=O)O[C@H]C=CC=O)OC5)))))C[C@@]C)[C@H]C)C[C@@H][C@@][C@@H]6CCC[C@]6CO3)))))))COC=O)C)))))OC=O)C)))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=C(CCC2CCCC3C2CCCC32CO2)CO1
Scaffold Graph/Node level: OC1CC(CCC2CCCC3C2CCCC32CO2)CO1
Scaffold Graph level: CC1CCC(CCC2CCCC3C2CCCC32CC2)C1
Functional groups: CC(=O)OC; COC(C)=O; CC1=CC(=O)OC1; C[C@@]1(C)CO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tetracarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
ajugamarin f4
External chemical identifiers:
CID:CID_14356990
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 534.65
Log P RDKit 3.91
Topological polar surface area (Å2) RDKit 117.73
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.79
Number of rotatable bonds RDKit 12
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 0
Number of aromatic rings RDKit 0
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
[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25
[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
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 -7.01
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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