IMPPAT Phytochemical information: 
Mammeisin
Mammeisin
Summary

SMILES: CC(CC(=O)c1c(O)c2c(cc(=O)oc2c(c1O)CC=C(C)C)c1ccccc1)C
InChI: InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)22(19(26)12-15(3)4)24(29)21-18(13-20(27)30-25(17)21)16-8-6-5-7-9-16/h5-10,13,15,28-29H,11-12H2,1-4H3
InChIKey: JIFOADIANOIMSK-UHFFFAOYSA-N
DeepSMILES: CCCC=O)ccO)cccc=O)oc6cc%10O))CC=CC)C)))))))))cccccc6))))))))))))C
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)c2ccccc2o1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)C2CCCCC2O1
Scaffold Graph level: CC1CC2CCCCC2C(C2CCCCC2)C1
Functional groups: cC(C)=O; cO; c=O; coc; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Neoflavonoids
ClassyFire Subclass: Prenylated neoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
mammea a/aa, Mammeisin, mammeisin
External chemical identifiers:
CID:CID_5281419; ChEMBL:CHEMBL194485; ChEBI:CHEBI:69990; SureChEMBL:SCHEMBL6913744
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Mammeisin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 406.48
Log P RDKit 5.61
Topological polar surface area (Å2) RDKit 87.74
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.28
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
Mammeisin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.315595
Mammeisin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.66
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 Yes
P-glycoprotein substrate SwissADME No