IMPPAT Phytochemical information: 
methyl (E)-trans-alpha-2,3-epoxybergamota-2,10-dien-12-oate

methyl (E)-trans-alpha-2,3-epoxybergamota-2,10-dien-12-oate
Summary

SMILES: COC(=O)/C(=C/CC[C@]1(C)[C@H]2CC3C([C@@H]1C2)(C)O3)/C
InChI: InChI=1S/C16H24O3/c1-10(14(17)18-4)6-5-7-15(2)11-8-12(15)16(3)13(9-11)19-16/h6,11-13H,5,7-9H2,1-4H3/b10-6+/t11-,12-,13?,15-,16?/m1/s1
InChIKey: YNLCLDZXTPYXSM-HICBEHQQSA-N
DeepSMILES: COC=O)/C=C/CC[C@]C)[C@H]CCC[C@@H]6C6))C)O3)))))))))/C
Scaffold Graph/Node/Bond level: C1C2CC1C1OC1C2
Scaffold Graph/Node level: C1C2CC1C1OC1C2
Scaffold Graph level: C1C2CC1C1CC1C2
Functional groups: C/C=C(\C)C(=O)OC; CC1OC1(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Monoterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Bergamotane sesquiterpenoids|Santalane sesquiterpenoids
Synonymous chemical names:
methyl (e)-trans-α-2,3-epoxybergamota-2,10-dien-12-oate
External chemical identifiers:
CID:CID_91747480
Chemical structure download


methyl (E)-trans-alpha-2,3-epoxybergamota-2,10-dien-12-oate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.37
Log P RDKit 3.09
Topological polar surface area (Å2) RDKit 38.83
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


methyl (E)-trans-alpha-2,3-epoxybergamota-2,10-dien-12-oate
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.444771


methyl (E)-trans-alpha-2,3-epoxybergamota-2,10-dien-12-oate
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.70
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No