IMPPAT Phytochemical information: 
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylate
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)C2=CC[C@H](CC2)C(=C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H24O7/c1-8(2)9-3-5-10(6-4-9)15(21)23-16-14(20)13(19)12(18)11(7-17)22-16/h5,9,11-14,16-20H,1,3-4,6-7H2,2H3/t9-,11-,12-,13+,14-,16+/m1/s1
InChIKey: CDSQRAACZGXZNE-MMNFBHMQSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)C=CC[C@H]CC6))C=C)C))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CCCCO1)C1=CCCCC1
Scaffold Graph/Node level: OC(OC1CCCCO1)C1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)C1CCCCC1
Functional groups: CO; CC=C(C(=O)O[C@@H](C)OC)C; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Menthane monoterpenoids|Monocyclic monoterpenoids
Synonymous chemical names:
perilloside b, Perilloside B
External chemical identifiers:
CID:CID_21631012; ZINC:ZINC000145901122
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.36
Log P RDKit -0.37
Topological polar surface area (Å2) RDKit 116.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.68
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 Yes