IMPPAT Phytochemical information: 
[(4aR,7R,7aR)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
[(4aR,7R,7aR)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
Summary

SMILES: CC(CC(=O)OC1OC=C([C@@]2([C@@H]1[C@@]1(CO1)C(C2)OC(=O)C)O)COC(=O)C(C(C)C)OC(=O)CC(C)C)C
InChI: InChI=1S/C27H40O11/c1-14(2)8-20(29)37-22(16(5)6)24(31)33-11-18-12-34-25(38-21(30)9-15(3)4)23-26(18,32)10-19(36-17(7)28)27(23)13-35-27/h12,14-16,19,22-23,25,32H,8-11,13H2,1-7H3/t19?,22?,23-,25?,26+,27-/m1/s1
InChIKey: QPMVBTMUWDUUTJ-KUTRIIDVSA-N
DeepSMILES: CCCC=O)OCOC=C[C@@][C@@H]6[C@@]CO3))CC5)OC=O)C))))))O))COC=O)CCC)C))OC=O)CCC)C))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CCC3(CO3)C2CO1
Scaffold Graph/Node level: C1CC2CCC3(CO3)C2CO1
Scaffold Graph level: C1CCC2C(C1)CCC21CC1
Functional groups: CC(=O)OC1CCC(C)=CO1; C[C@@]1(C)CO1; COC(C)=O; CO
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: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
ivhd-valtrate
External chemical identifiers:
CID:CID_129317364
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(4aR,7R,7aR)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 540.61
Log P RDKit 2.42
Topological polar surface area (Å2) RDKit 147.19
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 15
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
[(4aR,7R,7aR)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.234009
[(4aR,7R,7aR)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.84
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No