IMPPAT Phytochemical information: 
Crocetin monogentibiosyl ester
Crocetin monogentibiosyl ester
Summary

SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@H](OC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)O)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/C32H44O14/c1-17(11-7-13-19(3)29(40)41)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(39)26(37)24(35)22(45-32)16-43-31-27(38)25(36)23(34)21(15-33)44-31/h5-14,21-28,31-39H,15-16H2,1-4H3,(H,40,41)/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+/t21-,22-,23-,24-,25+,26+,27-,28-,31-,32-/m1/s1
InChIKey: VULLCGFNYWDRHL-CCHFYQIXSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]O[C@H]OC=O)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=O)O))C)))))C))))))/C)))))/C))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCC(COC2CCCCO2)OC1
Scaffold Graph/Node level: C1CCC(COC2CCCCO2)OC1
Scaffold Graph level: C1CCC(CCC2CCCCC2)CC1
Functional groups: CC(/C=C/C=C(C)C(=O)O)=CC=CC=C(C)C=CC=C(/C)C(=O)O[C@H](C)OC; CO; CO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Miscellaneous apocarotenoids
Synonymous chemical names:
crocetin monogentibiosyl ester
External chemical identifiers:
CID:44575352; ChEMBL:CHEMBL500492; ZINC:ZINC000049889479
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Crocetin monogentibiosyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 652.69
Log P RDKit -0.31
Topological polar surface area (Å2) RDKit 232.9
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 14
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Crocetin monogentibiosyl ester
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.0725
Crocetin monogentibiosyl ester
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -8.61
Number of PAINS structural alerts SwissADME 1.0
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 Yes
P-glycoprotein substrate SwissADME Yes