IMPPAT Phytochemical information: 
Khelmarin A
Khelmarin A
Summary

SMILES: C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc(=O)cc2)O[C@@H]1c2c(ccc3c2oc(=O)cc3)OC([C@@H]1O)(C)C)(C)C
InChI: InChI=1S/C33H32O8/c1-8-31(2,3)24-27-18(11-14-22(35)38-27)26(19-15-16-32(4,5)41-28(19)24)39-29-23-20(40-33(6,7)30(29)36)12-9-17-10-13-21(34)37-25(17)23/h8-16,29-30,36H,1H2,2-7H3/t29-,30-/m1/s1
InChIKey: KEMANLIKQHOKAN-LOYHVIPDSA-N
DeepSMILES: C=CCccOCC)C)C=Cc6ccc%10oc=O)cc6))))))O[C@@H]cccccc6oc=O)cc6))))))))OC[C@@H]6O))C)C)))))))))))))))C)C
Scaffold Graph/Node/Bond level: O=c1ccc2c(OC3CCOc4ccc5ccc(=O)oc5c43)c3c(cc2o1)OCC=C3
Scaffold Graph/Node level: OC1CCC2C(CC3OCCCC3C2OC2CCOC3CCC4CCC(O)OC4C32)O1
Scaffold Graph level: CC1CCC2C(C1)CC1CCCCC1C2CC1CCCC2CCC3CCC(C)CC3C21
Functional groups: C=CC; CO; c=O; cC=CC; cOC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Pyranocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins
Synonymous chemical names:
khelmarin a
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Khelmarin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 556.61
Log P RDKit 6.2
Topological polar surface area (Å2) RDKit 108.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 4
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 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
Khelmarin A
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 Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2339
Khelmarin A
ADMET 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -5.43
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No