IMPPAT Phytochemical information: 
Dihydroisomorellin

Dihydroisomorellin
Summary

SMILES: O=C/C(=C/C[C@@]12OC(C3[C@@]42Oc2c(CC=C(C)C)c5OC(C)(C)C=Cc5c(c2C(=O)C4C[C@H](C1=O)C3)O)(C)C)/C
InChI: InChI=1S/C33H38O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,16,19,22-23,35H,9,13-15H2,1-7H3/b18-10+/t19-,22?,23?,32+,33-/m0/s1
InChIKey: ORNMPVMTDJIPQS-NXABCWRFSA-N
DeepSMILES: O=C/C=C/C[C@]OCC[C@]5OccCC=CC)C))))cOCC)C)C=Cc6cc%10C=O)C%14C[C@H]C%21=O))C%18))))))O)))))))))))))C)C))))))/C
Scaffold Graph/Node/Bond level: O=C1c2cc3c(cc2OC24C5COC2C(=O)C(C5)CC14)OCC=C3
Scaffold Graph/Node level: OC1C2CC3CCCOC3CC2OC23C4COC2C(O)C(C4)CC13
Scaffold Graph level: CC1C2CC3CCC1C31CC3CC4CCCCC4CC3C(C)C1C2
Functional groups: C/C=C(\C)C=O; CC(=O)C; cO; COC; cOC; CC=C(C)C; cC=CC; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Meroterpenoids
Synonymous chemical names:
dihydroisomorellin
External chemical identifiers:
CID:CID_16078255; ChEMBL:CHEMBL3809753
Chemical structure download


Dihydroisomorellin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 546.66
Log P RDKit 5.71
Topological polar surface area (Å2) RDKit 99.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Dihydroisomorellin
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 0.287032


Dihydroisomorellin
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 -5.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes