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; cOC; CO; cC=CC; coc; c=O
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 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.23
Khelmarin A
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -5.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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