IMPPAT Phytochemical information: 
Ajugapantin A
Ajugapantin A
Summary

SMILES: CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1[C@@H](CC[C@@]12CO1)OC(=O)C)(C)C[C@@H](C1=CC(=O)OC1)OC(=O)C)C
InChI: InChI=1S/C28H38O11/c1-15-9-23(39-19(5)32)28(14-35-16(2)29)25(21(37-17(3)30)7-8-27(28)13-36-27)26(15,6)11-22(38-18(4)31)20-10-24(33)34-12-20/h10,15,21-23,25H,7-9,11-14H2,1-6H3/t15-,21-,22+,23+,25-,26+,27+,28-/m1/s1
InChIKey: KBIJVGBQDPMKKO-BAOLRMIKSA-N
DeepSMILES: CC=O)OC[C@@][C@@H]OC=O)C)))C[C@H][C@][C@H]6[C@@H]CC[C@]%10CO3)))))OC=O)C)))))C)C[C@@H]C=CC=O)OC5)))))OC=O)C))))))C
Scaffold Graph/Node/Bond level: O=C1C=C(CCC2CCCC3C2CCCC32CO2)CO1
Scaffold Graph/Node level: OC1CC(CCC2CCCC3C2CCCC32CO2)CO1
Scaffold Graph level: CC1CCC(CCC2CCCC3C2CCCC32CC2)C1
Functional groups: COC(C)=O; CC(=O)OC; C[C@@]1(C)CO1; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Pentacarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
ajugapantin a
External chemical identifiers:
CID:CID_12136681; ChEMBL:CHEMBL522544; ChEBI:CHEBI:69885; ZINC:ZINC000042890374
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ajugapantin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 550.6
Log P RDKit 2.43
Topological polar surface area (Å2) RDKit 144.03
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Ajugapantin A
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 3
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 0.25
Ajugapantin A
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 -8.52
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No