IMPPAT Phytochemical information: 
Microhelenin B
Microhelenin B
Summary

SMILES: CCC(C(=O)O[C@H]1[C@H]2[C@@H](C[C@H]([C@H]3[C@@]1(C)C(=O)C=C3)C)OC(=O)[C@H]2C)C
InChI: InChI=1S/C20H28O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h7-8,10-14,16-17H,6,9H2,1-5H3/t10?,11-,12+,13+,14-,16-,17+,20+/m1/s1
InChIKey: VSRLMYQKLUPERI-JCQBEPMYSA-N
DeepSMILES: CCCC=O)O[C@H][C@H][C@@H]C[C@H][C@H][C@@]7C)C=O)C=C5)))))C)))OC=O)[C@H]5C)))))))))C
Scaffold Graph/Node/Bond level: O=C1CC2CC3C(=O)C=CC3CCC2O1
Scaffold Graph/Node level: OC1CC2CC3C(O)CCC3CCC2O1
Scaffold Graph level: CC1CC2CCC3CCC(C)C3CC2C1
Functional groups: CC(=O)OC; O=C1C=CCC1; COC(=O)C
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: Pseudoguaiane sesquiterpenoids
Synonymous chemical names:
microhelenin b
External chemical identifiers:
CID:CID_182376
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Microhelenin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 348.44
Log P RDKit 2.92
Topological polar surface area (Å2) RDKit 69.67
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
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
Microhelenin B
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73
Microhelenin B
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 -6.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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