IMPPAT Phytochemical information: 
15-Demethyl plumieride
15-Demethyl plumieride
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@]2(C=C3)C=C(C(=O)O2)CO)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H24O12/c1-28-17(27)10-7-29-18(31-19-15(25)14(24)13(23)11(6-22)30-19)12-9(10)2-3-20(12)4-8(5-21)16(26)32-20/h2-4,7,9,11-15,18-19,21-25H,5-6H2,1H3/t9-,11-,12-,13-,14+,15-,18+,19+,20-/m1/s1
InChIKey: XFIOZCMKPNZOII-RJMCEWFISA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@]C=C5))C=CC=O)O5))CO)))))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=CC2(C=CC3C=COC(OC4CCCCO4)C32)O1
Scaffold Graph/Node level: OC1CCC2(CCC3CCOC(OC4CCCCO4)C32)O1
Scaffold Graph level: CC1CCC2(CCC3CCCC(CC4CCCCC4)C32)C1
Functional groups: CO; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; CC=CC; CC1=CCOC1=O
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: Iridoids monoterpenoids
Synonymous chemical names:
iridoids, 8-O-acetylharpagid (iridoid), iridoid
External chemical identifiers:
CID:CID_453214
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
15-Demethyl plumieride
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.4
Log P RDKit -2.77
Topological polar surface area (Å2) RDKit 181.44
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
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 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
15-Demethyl plumieride
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
15-Demethyl plumieride
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.23
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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