IMPPAT Phytochemical information: 
[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
Summary

SMILES: OC[C@]12O[C@H]1[C@H]1[C@H]3OC45O[C@]1([C@H]1[C@@]([C@@H]2O)(O)[C@@H](OC(=O)c2ccccc2)[C@H]([C@@H]1[C@@H](C)CCCCCCC5)C)[C@@H](C[C@@]3(O4)C(=C)C)C
InChI: InChI=1S/C37H50O9/c1-20(2)33-18-22(4)37-26-29(33)44-35(45-33,46-37)17-13-8-6-7-10-14-21(3)25-23(5)28(42-31(39)24-15-11-9-12-16-24)36(41,27(25)37)32(40)34(19-38)30(26)43-34/h9,11-12,15-16,21-23,25-30,32,38,40-41H,1,6-8,10,13-14,17-19H2,2-5H3/t21-,22+,23-,25-,26+,27+,28-,29+,30-,32+,33+,34-,35?,36+,37+/m0/s1
InChIKey: IAPHKDDUYAWCMB-BLZWUUDBSA-N
DeepSMILES: OC[C@]O[C@H]3[C@H][C@H]OCO[C@]6[C@H][C@@][C@@H]%12O))O)[C@@H]OC=O)cccccc6))))))))[C@H][C@@H]5[C@@H]C)CCCCCCC%16)))))))))C)))))[C@@H]C[C@@]8O7)C=C)C))))C
Scaffold Graph/Node/Bond level: O=C(OC1CC2CCCCCCCCC34OC5CCC6(O3)C2C1CC1OC1C6C5O4)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCCCCCCCC34OC5CCC6(O3)C2C1CC1OC1C6C5O4)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCCCCCCCC34CC5CCC6(C3)C2C1CC1CC1C6C5C4)C1CCCCC1
Functional groups: CO; C[C@]1(C)O[C@H]1C; CC1(OC)OCCO1; C=C(C)C; cC(=O)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: Diterpenoids
NP Classifier Class: Daphnane diterpenoids
Synonymous chemical names:
pimelea factor p2
External chemical identifiers:
CID:CID_44559301; ChEMBL:CHEMBL507954
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 638.8
Log P RDKit 4.52
Topological polar surface area (Å2) RDKit 127.21
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25
[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.83
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 Yes