IMPPAT Phytochemical information: 
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-[(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-[(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
Summary

SMILES: O[C@@H]1C[C@@]2(C)OC(C=C2C(C1)(C)C)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)\C)\C)/C)/C
InChI: InChI=1S/C40H56O4/c1-27(17-13-19-29(3)33-21-35-37(5,6)23-31(41)25-39(35,9)43-33)15-11-12-16-28(2)18-14-20-30(4)34-22-36-38(7,8)24-32(42)26-40(36,10)44-34/h11-22,31-34,41-42H,23-26H2,1-10H3/b12-11+,17-13+,18-14+,27-15+,28-16+,29-19+,30-20+/t31-,32-,33?,34?,39+,40+/m0/s1
InChIKey: YLUSVJDFTAATNS-RFIAJWJGSA-N
DeepSMILES: O[C@@H]C[C@@]C)OCC=C5CC9)C)C))))/C=C/C=C/C=C/C=C/C=C/C=C/C=C/CC=C[C@@]O5)C)C[C@H]CC6C)C)))O)))))))\C)))))\C))))))/C)))))/C
Scaffold Graph/Node/Bond level: C(=CC=CC=CC=CC1C=C2CCCCC2O1)C=CC=CC=CC1C=C2CCCCC2O1
Scaffold Graph/Node level: C(CCCCCCCC1CC2CCCCC2O1)CCCCCCC1CC2CCCCC2O1
Scaffold Graph level: C(CCCCCCCC1CC2CCCCC2C1)CCCCCCC1CC2CCCCC2C1
Functional groups: CO; COC; CC=C(C)C; C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(/C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Tetraterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Carotenoids (C40)
NP Classifier Class: Carotenoids (C40, β-β)
Synonymous chemical names:
auroxanthin
External chemical identifiers:
CID:CID_134781708
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-[(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 600.88
Log P RDKit 8.97
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 8
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-[(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
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 0.22
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-[(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.36
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