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; CC1=CC(=O)OC1; COC(C)=O; 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: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 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
[(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
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 2.0
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