IMPPAT Phytochemical information: 
Deoxyandrographolide

Deoxyandrographolide
Summary

SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C2CCC1=CCOC1=O)C)C
InChI: InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,16-17,21-22H,4-8,10-12H2,1-3H3/t16-,17+,19-,20-/m0/s1
InChIKey: DAXSYTVXDSOSIE-HNJRGHQBSA-N
DeepSMILES: OC[C@]C)[C@H]O)CC[C@@][C@@H]6CCC=C6CCC=CCOC5=O)))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C1OCC=C1CCC1=CCCC2CCCCC12
Scaffold Graph/Node level: OC1OCCC1CCC1CCCC2CCCCC21
Scaffold Graph level: CC1CCCC1CCC1CCCC2CCCCC21
Functional groups: CO; CC(C)=C(C)C; CC1=CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids|Secolabdane diterpenoids
Synonymous chemical names:
deoxyandrographolide, Deoxyandrographolide
External chemical identifiers:
CID:CID_21679042; ChEMBL:CHEMBL4454267; ZINC:ZINC000021992845; MolPort-005-938-522
Chemical structure download


Deoxyandrographolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 334.46
Log P RDKit 3.14
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Deoxyandrographolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.612167


Deoxyandrographolide
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.28
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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