IMPPAT Phytochemical information: 
(1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylic acid
(1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylic acid
Summary

SMILES: O[C@H]1C[C@@H](C(=O)O)[C@@H]2[C@@H](C1)[C@]1(C)C[C@@H](O[C@]31C[C@@H]2OC3=O)c1cocc1
InChI: InChI=1S/C19H22O7/c1-18-6-13(9-2-3-24-8-9)26-19(18)7-14(25-17(19)23)15-11(16(21)22)4-10(20)5-12(15)18/h2-3,8,10-15,20H,4-7H2,1H3,(H,21,22)/t10-,11+,12+,13+,14-,15+,18-,19+/m0/s1
InChIKey: UYALWPKCIMKALF-YHPVUIEZSA-N
DeepSMILES: O[C@H]C[C@@H]C=O)O))[C@@H][C@@H]C6)[C@]C)C[C@@H]O[C@@]5C[C@@H]9OC5=O)))))))ccocc5
Scaffold Graph/Node/Bond level: O=C1OC2CC13OC(c1ccoc1)CC3C1CCCCC21
Scaffold Graph/Node level: OC1OC2CC13OC(C1CCOC1)CC3C1CCCCC21
Scaffold Graph level: CC1CC2CC13CC(C1CCCC1)CC3C1CCCCC21
Functional groups: CO; CC(=O)O; COC; COC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
diosbulbin c, diosbulbin-c
External chemical identifiers:
CID:CID_91895309; ZINC:ZINC000006032344; MolPort-035-705-825
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.38
Log P RDKit 1.9
Topological polar surface area (Å2) RDKit 106.2
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 2
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylic acid
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 0.77
(1S,3R,5S,6R,8R,10R,11S,12S)-3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.01,5.06,11]pentadecane-10-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.72
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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