IMPPAT Phytochemical information: 
(1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
(1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
Summary

SMILES: CCC(C1(O)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)C(C(OC(=O)C1O)C)(O)C(C)C)(O)C
InChI: InChI=1S/C23H35NO10/c1-6-21(5,29)23(31)17(25)18(26)33-13(4)22(30,12(2)3)19(27)32-11-14-7-9-24-10-8-15(16(14)24)34-20(23)28/h7,12-13,15-17,25,29-31H,6,8-11H2,1-5H3/t13?,15-,16-,17?,21?,22?,23?/m1/s1
InChIKey: ZMTPMWQLYFVWSP-YHWJFGDTSA-N
DeepSMILES: CCCCO)C=O)O[C@@H]CCN[C@@H]5C=CC5))COC=O)CCOC=O)C%17O))))C))O)CC)C)))))))))))))))O)C
Scaffold Graph/Node/Bond level: O=C1CCC(=O)OC2CCN3CC=C(COC(=O)CCO1)C23
Scaffold Graph/Node level: OC1CCC(O)OC2CCN3CCC(COC(O)CCO1)C23
Scaffold Graph level: CC1CCCC(C)CCC2CCC3CCC(CC(C)CC1)C23
Functional groups: CO; CC(=O)OC; CN(C)C; CC=C(C)C; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
Spiracine
External chemical identifiers:
CID:CID_157017
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 485.53
Log P RDKit -0.96
Topological polar surface area (Å2) RDKit 163.06
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3
(1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
Drug-likeness properties
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 2
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 0.221165
(1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.20
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