IMPPAT Phytochemical information: 
Amarogentin
Amarogentin
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@H]([C@H]2C=C)CCOC3=O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1c(O)cc(cc1c1cccc(c1)O)O
InChI: InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
InChIKey: DBOVHQOUSDWAPQ-WTONXPSSSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@H][C@H]6C=C)))CCOC6=O)))))))))))[C@@H][C@H][C@@H]6O))O))OC=O)ccO)cccc6cccccc6)O))))))))O
Scaffold Graph/Node/Bond level: O=C1OCCC2CC(OC3OCCCC3OC(=O)c3ccccc3-c3ccccc3)OC=C12
Scaffold Graph/Node level: OC1OCCC2CC(OC3OCCCC3OC(O)C3CCCCC3C3CCCCC3)OCC21
Scaffold Graph level: CC1CCCC2CC(CC3CCCCC3CC(C)C3CCCCC3C3CCCCC3)CCC12
Functional groups: CO; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; C=CC; cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Biphenyls and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Secoiridoid monoterpenoids
Synonymous chemical names:
chiratin, amarogentin
External chemical identifiers:
CID:CID_115149; ChEBI:CHEBI:2622; ZINC:ZINC000003982136; FDASRS:5L82GT5I0W; SureChEMBL:SCHEMBL1031187; MolPort-005-945-187
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Amarogentin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 586.55
Log P RDKit 1.06
Topological polar surface area (Å2) RDKit 201.67
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Amarogentin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
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 0.198789
Amarogentin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.16
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