IMPPAT Phytochemical information: 
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
Summary

SMILES: COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)C1CC[C@@]2(C(=CC(=O)O[C@H]2c2cocc2)C1=C)C
InChI: InChI=1S/C27H32O6/c1-16-18(26(4)11-8-21(28)25(2,3)20(26)14-22(29)31-6)7-10-27(5)19(16)13-23(30)33-24(27)17-9-12-32-15-17/h8-9,11-13,15,18,20,24H,1,7,10,14H2,2-6H3/t18?,20-,24-,26+,27+/m0/s1
InChIKey: CUJHOPQCBJBWQL-GJGRSQDYSA-N
DeepSMILES: COC=O)C[C@@H][C@]C)C=CC=O)C6C)C)))))CCC[C@@]C=CC=O)O[C@H]6ccocc5)))))))))C6=C)))C
Scaffold Graph/Node/Bond level: C=C1C2=CC(=O)OC(c3ccoc3)C2CCC1C1C=CC(=O)CC1
Scaffold Graph/Node level: CC1C(C2CCC(O)CC2)CCC2C1CC(O)OC2C1CCOC1
Scaffold Graph level: CC1CCC(C2CCC3C(C4CCCC4)CC(C)CC3C2C)CC1
Functional groups: COC(C)=O; CC(=O)C=CC; C=C(C)C1=CC(=O)OCC1; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyrans
ClassyFire Subclass: Pyranones and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
deoxyandirobin, Deoxyandirobin
External chemical identifiers:
CID:CID_6708516; ChEMBL:CHEMBL3039353; ChEBI:CHEBI:93790
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 452.55
Log P RDKit 5.13
Topological polar surface area (Å2) RDKit 82.81
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.589366
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.26
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
2-[(1R,2R)-2-[(1R,8aR)-1-(3-furanyl)-8a-methyl-5-methylene-3-oxo-1,6,7,8-tetrahydro-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxo-1-cyclohex-3-enyl]acetic acid methyl ester
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL