IMPPAT Phytochemical information: 
(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(((4aR,8aS)-4-isopropyl-1,7-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(((4aR,8aS)-4-isopropyl-1,7-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol
Summary

SMILES: OC[C@@H]1O[C@H](OC[C@@H]2O[C@H](OC3(C)CCC([C@@H]4[C@@H]3CC(=CC4)C)C(C)C)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C27H46O11/c1-12(2)14-7-8-27(4,16-9-13(3)5-6-15(14)16)38-26-24(34)22(32)20(30)18(37-26)11-35-25-23(33)21(31)19(29)17(10-28)36-25/h5,12,14-26,28-34H,6-11H2,1-4H3/t14?,15-,16+,17+,18+,19+,20+,21-,22-,23+,24+,25+,26-,27?/m1/s1
InChIKey: QTUUQMSYZBNFDW-BLJQVZHCSA-N
DeepSMILES: OC[C@@H]O[C@H]OC[C@@H]O[C@H]OCC)CCC[C@@H][C@@H]6CC=CC6))C)))))CC)C)))))))[C@H][C@@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CCC2C(C1)CCCC2OC1CCCC(COC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OCC2CCCC(OC3CCCC4CCCCC43)O2)OC1
Scaffold Graph level: C1CCC(CCC2CCCC(CC3CCCC4CCCCC43)C2)CC1
Functional groups: CO; CO[C@H](C)OC; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Cadinane sesquiterpenoids
Synonymous chemical names:
sesquiterpene alcohol
External chemical identifiers:
CID:CID_91754221
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(((4aR,8aS)-4-isopropyl-1,7-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 546.65
Log P RDKit -0.58
Topological polar surface area (Å2) RDKit 178.53
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 7
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(((4aR,8aS)-4-isopropyl-1,7-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2
(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(((4aR,8aS)-4-isopropyl-1,7-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.84
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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