IMPPAT Phytochemical information: 
Mesuanic acid
Mesuanic acid
Summary

SMILES: CC(CCC(=C(C)C)CC1(CC=C(C)C)C2=C(C(=O)C(C(O2)C)C)C(=C(C1=O)C(c1ccccc1)CC(=O)O)O)C
InChI: InChI=1S/C35H46O6/c1-20(2)14-15-26(22(5)6)19-35(17-16-21(3)4)33(40)29(27(18-28(36)37)25-12-10-9-11-13-25)32(39)30-31(38)23(7)24(8)41-34(30)35/h9-13,16,20,23-24,27,39H,14-15,17-19H2,1-8H3,(H,36,37)
InChIKey: NZOISPAPLOZNLH-UHFFFAOYSA-N
DeepSMILES: CCCCC=CC)C))CCCC=CC)C))))C=CC=O)CCO6)C))C)))C=CC6=O))Ccccccc6))))))CC=O)O)))))O)))))))))C
Scaffold Graph/Node/Bond level: O=C1CC2=C(C=C1Cc1ccccc1)C(=O)CCO2
Scaffold Graph/Node level: OC1CC2OCCC(O)C2CC1CC1CCCCC1
Scaffold Graph level: CC1CC2CCCC(C)C2CC1CC1CCCCC1
Functional groups: CC(=O)O; CC(C)=C(C)C; CC1=C(O)C2=C(CC1=O)OCCC2=O; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Phenylpropanoic acids
NP Classifier Biosynthetic pathway: Polyketides|Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Polyprenylated cyclic polyketides (Hop meroterpenoids)
Synonymous chemical names:
mesuanic acid
External chemical identifiers:
CID:101277421
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Mesuanic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.75
Log P RDKit 8.02
Topological polar surface area (Å2) RDKit 100.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.51
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Mesuanic acid
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 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2649
Mesuanic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.89
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes