IMPPAT Phytochemical information: 
2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,8,9,11a-decahydro-7,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4R*(Z),6R*,7S*,9R*,10Z,11aR*))-

2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,8,9,11a-decahydro-7,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4R*(Z),6R*,7S*,9R*,10Z,11aR*))-
Summary

SMILES: C/C=C(/C(=O)O[C@@H]1C[C@@]2(C)O[C@](C[C@@H]2O)(/C(=C\[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)\C
InChI: InChI=1S/C20H26O7/c1-6-10(2)17(22)26-14-8-19(5)15(21)9-20(24,27-19)11(3)7-13-16(14)12(4)18(23)25-13/h6-7,13-16,21,24H,4,8-9H2,1-3,5H3/b10-6+,11-7-/t13-,14-,15+,16+,19-,20-/m1/s1
InChIKey: WGVJNQGTZSPMCY-RPBBZJPTSA-N
DeepSMILES: C/C=C/C=O)O[C@@H]C[C@@]C)O[C@]C[C@@H]5O)))/C=C\[C@@H][C@@H]9C=C)C=O)O5))))))/C))O))))))))\C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C=CC3CCC(CCC12)O3
Scaffold Graph/Node level: CC1C(O)OC2CCC3CCC(CCC21)O3
Scaffold Graph level: CC1CC2CCC3CCC(CCC2C1C)C3
Functional groups: C/C=C(\C)C(=O)OC; C/C(=C/C)[C@@](O)(C)OC; CO; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
niveusin c
External chemical identifiers:
CID:CID_5320177; ZINC:ZINC000033833054
Chemical structure download


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,8,9,11a-decahydro-7,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4R*(Z),6R*,7S*,9R*,10Z,11aR*))-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 378.42
Log P RDKit 1.54
Topological polar surface area (Å2) RDKit 102.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
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 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
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 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,8,9,11a-decahydro-7,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4R*(Z),6R*,7S*,9R*,10Z,11aR*))-
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 0.426816


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,8,9,11a-decahydro-7,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4R*(Z),6R*,7S*,9R*,10Z,11aR*))-
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 -8.11
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes