IMPPAT Phytochemical information: 
Lolitrem B
Lolitrem B
Summary

SMILES: CC(=C[C@H]1O[C@H]2[C@H]3O[C@]43[C@@H](O[C@@H]2C(O1)(C)C)CC[C@]1([C@@]4(O)CC[C@@H]2[C@]1(C)c1[nH]c3c(c1C2)c1C[C@@H]2[C@@H](C(=O)c1cc3)C(OC2(C)C)(C)C)C)C
InChI: InChI=1S/C42H55NO7/c1-20(2)17-28-47-32-34(38(7,8)48-28)46-27-14-15-39(9)40(10)21(13-16-41(39,45)42(27)35(32)49-42)18-24-29-23-19-25-30(37(5,6)50-36(25,3)4)31(44)22(23)11-12-26(29)43-33(24)40/h11-12,17,21,25,27-28,30,32,34-35,43,45H,13-16,18-19H2,1-10H3/t21-,25+,27-,28-,30-,32+,34-,35+,39+,40+,41-,42-/m0/s1
InChIKey: HGBZMCXKHKZYBF-WZGHVFPCSA-N
DeepSMILES: CC=C[C@H]O[C@H][C@H]O[C@@]3[C@@H]O[C@@H]7CO%11)C)C))))CC[C@][C@@]6O)CC[C@@H][C@]6C)c[nH]ccc5C8))cC[C@@H][C@@H]C=O)c6cc%10))))COC5C)C)))C)C)))))))))))))))C))))))))))))C
Scaffold Graph/Node/Bond level: O=C1c2ccc3[nH]c4c(c3c2CC2COCC12)CC1CCC2C(CCC3OC5COCOC5C5OC325)C41
Scaffold Graph/Node level: OC1C2COCC2CC2C1CCC1NC3C(CC4CCC5C(CCC6OC7COCOC7C7OC657)C43)C12
Scaffold Graph level: CC1C2CCCC2CC2C1CCC1CC3C(CC4CCC5C(CCC6CC7CCCCC7C7CC675)C43)C12
Functional groups: CO[C@@H](C=C(C)C)OC; cC(=O)C; C[C@H]1O[C@]1(C)C; COC; CO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Indole-Diterpenoid alkaloids (Penitrems)
Synonymous chemical names:
Lolitrem B
External chemical identifiers:
CID:CID_11947793; ZINC:ZINC000085596987; FDASRS:4M63MT6W6M
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lolitrem B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 685.9
Log P RDKit 6.87
Topological polar surface area (Å2) RDKit 102.54
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 42
Number of heavy atoms RDKit 50
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 31
Shape complexity RDKit 0.74
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Lolitrem B
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 0.25
Lolitrem B
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 -6.34
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No