IMPPAT Phytochemical information: 
Macrocarposide
Macrocarposide
Summary

SMILES: OCC1O[C@H](C([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)C(=O)C(CO2)c1ccc(cc1O)O
InChI: InChI=1S/C21H22O11/c22-5-13-17(27)19(29)20(30)21(32-13)14-11(25)4-12-15(18(14)28)16(26)9(6-31-12)8-2-1-7(23)3-10(8)24/h1-4,9,13,17,19-25,27-30H,5-6H2/t9?,13?,17-,19+,20?,21+/m1/s1
InChIKey: CGRZFWSCUINYCK-YACAPDLPSA-N
DeepSMILES: OCCO[C@H]C[C@H][C@@H]6O))O))O))ccO)cccc6O))C=O)CCO6))cccccc6O)))O
Scaffold Graph/Node/Bond level: O=C1c2cc(C3CCCCO3)ccc2OCC1c1ccccc1
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCC(C3CCCCO3)CC21
Scaffold Graph level: CC1C(C2CCCCC2)CCC2CCC(C3CCCCC3)CC21
Functional groups: CO; COC; cO; cC(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavonoid C-glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavanones
Synonymous chemical names:
macrocarposide, Macrocarposide
External chemical identifiers:
CID:CID_44257385
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Macrocarposide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 450.4
Log P RDKit -0.62
Topological polar surface area (Å2) RDKit 197.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Macrocarposide
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.296605
Macrocarposide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.23
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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