IMPPAT Phytochemical information: 
Andrographidine B
Andrographidine B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cccc(c2O)c2cc(=O)c3c(o2)c(OC)c(cc3O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C23H24O12/c1-31-14-7-11(26)16-10(25)6-13(33-22(16)21(14)32-2)9-4-3-5-12(17(9)27)34-23-20(30)19(29)18(28)15(8-24)35-23/h3-7,15,18-20,23-24,26-30H,8H2,1-2H3/t15-,18-,19+,20-,23-/m1/s1
InChIKey: JCUIPEIMZRLNKQ-BSTKLLGTSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6O))ccc=O)cco6)cOC))ccc6O)))OC)))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2cccc(OC3CCCCO3)c2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCC(OC3CCCCO3)C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC(CC3CCCCC3)C2)CC2CCCCC12
Functional groups: CO; cO[C@@H](C)OC; cO; c=O; coc; 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 b
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Andrographidine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.43
Log P RDKit 0.07
Topological polar surface area (Å2) RDKit 188.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 35
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 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 6
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 B
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 0.27
Andrographidine B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -8.74
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