IMPPAT Phytochemical information: 
[(3S,3aR,4R,5R,6R,7aS)-6-[(4S,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5
[(3S,3aR,4R,5R,6R,7aS)-6-[(4S,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5
View 3D structure using JSmol
Summary

SMILES: O=CO[C@H]1[C@H](OC(=O)CC(C)C)[C@@]2(C)[C@@H](CC(=O)[C@@]2(C(=C)[C@H]1[C@@]1(C)[C@@H](OC(=O)C)CC(=O)O[C@]2([C@@H]1CC(=O)OC2)C)O)c1ccoc1
InChI: InChI=1S/C34H42O13/c1-17(2)10-26(39)46-30-29(44-16-35)28(18(3)34(41)23(37)11-21(33(30,34)7)20-8-9-42-14-20)32(6)22-12-25(38)43-15-31(22,5)47-27(40)13-24(32)45-19(4)36/h8-9,14,16-17,21-22,24,28-30,41H,3,10-13,15H2,1-2,4-7H3/t21-,22-,24-,28+,29+,30-,31+,32+,33+,34+/m0/s1
InChIKey: BGIQNWKPRGQOMD-UVCADLPSSA-N
DeepSMILES: O=CO[C@H][C@H]OC=O)CCC)C)))))[C@@]C)[C@@H]CC=O)[C@@]5C=C)[C@H]9[C@@]C)[C@@H]OC=O)C)))CC=O)O[C@][C@@H]7CC=O)OC6)))))C)))))))))O))))cccoc5
Scaffold Graph/Node/Bond level: C=C1C(C2CCC(=O)OC3COC(=O)CC32)CCC2C1C(=O)CC2c1ccoc1
Scaffold Graph/Node level: CC1C(C2CCC(O)OC3COC(O)CC32)CCC2C(C3CCOC3)CC(O)C12
Scaffold Graph level: CC1CCC(C2CCC3C(C4CCCC4)CC(C)C3C2C)C2CC(C)CCC2C1
Functional groups: C=C(C)C; CC(=O)OC; CC(C)=O; CO; COC(C)=O; COC=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
rohitukin
External chemical identifiers:
CID:101835632
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(3S,3aR,4R,5R,6R,7aS)-6-[(4S,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 658.7
Log P RDKit 2.97
Topological polar surface area (Å2) RDKit 181.94
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
[(3S,3aR,4R,5R,6R,7aS)-6-[(4S,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5
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 3
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 0.1865
[(3S,3aR,4R,5R,6R,7aS)-6-[(4S,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.77
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 3.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes