IMPPAT Phytochemical information: 
2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-

2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-
Summary

SMILES: C/C=C(/C(=O)OC1C(O)/C(=C\CC(/C(=C\C2[C@@H]1C(=C)C(=O)O2)/C)O)/C)\C
InChI: InChI=1S/C20H26O6/c1-6-10(2)19(23)26-18-16-13(5)20(24)25-15(16)9-12(4)14(21)8-7-11(3)17(18)22/h6-7,9,14-18,21-22H,5,8H2,1-4H3/b10-6+,11-7-,12-9-/t14?,15?,16-,17?,18?/m0/s1
InChIKey: BXFQVBKJGJTIAT-CGSFVSGYSA-N
DeepSMILES: C/C=C/C=O)OCCO)/C=C\CC/C=C\C[C@@H]%10C=C)C=O)O5))))))/C))O))))/C))))))\C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C=CCCC=CCCC12
Scaffold Graph/Node level: CC1C(O)OC2CCCCCCCCC21
Scaffold Graph level: CC1CC2CCCCCCCCC2C1C
Functional groups: C/C=C(\C)C(=O)OC; CO; C/C=C(/C)C; 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:
zoapatanolide a, Zoapatanolide A
External chemical identifiers:
CID:CID_6448268
Chemical structure download


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.42
Log P RDKit 1.98
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.44


2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-
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 -7.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
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