IMPPAT Phytochemical information: 
Andrographidine D
Andrographidine D
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(OC)c(c3c2c(=O)cc(o3)c2cccc(c2OC)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C25H28O12/c1-31-13-7-5-6-11(22(13)33-3)14-8-12(27)18-15(9-16(32-2)23(34-4)24(18)35-14)36-25-21(30)20(29)19(28)17(10-26)37-25/h5-9,17,19-21,25-26,28-30H,10H2,1-4H3/t17-,19-,20+,21-,25-/m1/s1
InChIKey: PPQXLPYIRAWACL-PKPXASJOSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccOC))ccc6c=O)cco6)cccccc6OC)))OC))))))))))))OC)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2cccc(OC3CCCCO3)c12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCC(OC3CCCCO3)C12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCC(CC3CCCCC3)C12
Functional groups: CO; cO[C@@H](C)OC; cOC; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
andrographidine d
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Andrographidine D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 520.49
Log P RDKit 0.67
Topological polar surface area (Å2) RDKit 166.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
Andrographidine D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.33
Andrographidine D
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME 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 -8.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes