IMPPAT Phytochemical information: 
Ajugamacrin B
Ajugamacrin B
Summary

SMILES: CCC(C(=O)O[C@H](C1=CC(=O)OC1)C[C@@]1(C)[C@@H](C)C[C@H]([C@@]2([C@@H]1C(CC[C@]12CO1)OC(=O)C)COC(=O)C)OC(=O)C)C
InChI: InChI=1S/C31H44O11/c1-8-17(2)28(36)42-24(22-12-26(35)37-14-22)13-29(7)18(3)11-25(41-21(6)34)31(16-38-19(4)32)27(29)23(40-20(5)33)9-10-30(31)15-39-30/h12,17-18,23-25,27H,8-11,13-16H2,1-7H3/t17?,18-,23?,24-,25+,27+,29-,30+,31+/m0/s1
InChIKey: JPFTWOXTEMZXOG-TZSZWNSHSA-N
DeepSMILES: CCCC=O)O[C@H]C=CC=O)OC5)))))C[C@@]C)[C@@H]C)C[C@H][C@@][C@@H]6CCC[C@@]6CO3)))))OC=O)C)))))COC=O)C)))))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: CC(=O)OC; CC1=CC(=O)OC1; C[C@]1(C)CO1; COC(C)=O
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:
ajugamacrin b
External chemical identifiers:
CID:CID_101370736
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ajugamacrin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 592.68
Log P RDKit 3.46
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 31
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
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 24
Shape complexity RDKit 0.77
Number of rotatable bonds RDKit 14
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
Ajugamacrin 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 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
Ajugamacrin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately 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 -7.79
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No