IMPPAT Phytochemical information: 
Ajacine
Ajacine
Summary

SMILES: CO[C@H]1[C@@H]2[C@]3(CC[C@@H]([C@@]42[C@@H]([C@@]1(O)[C@@]1(O)C[C@@H]([C@H]2C[C@@H]4[C@@H]1[C@H]2OC)OC)N(C3)CC)OC)COC(=O)c1ccccc1NC(=O)C
InChI: InChI=1S/C34H48N2O9/c1-7-36-16-31(17-45-29(38)19-10-8-9-11-22(19)35-18(2)37)13-12-24(42-4)33-21-14-20-23(41-3)15-32(39,25(21)26(20)43-5)34(40,30(33)36)28(44-6)27(31)33/h8-11,20-21,23-28,30,39-40H,7,12-17H2,1-6H3,(H,35,37)/t20-,21-,23+,24+,25-,26+,27-,28+,30+,31+,32-,33+,34-/m1/s1
InChIKey: NUXFDCYXMLVOFU-AYBRVATOSA-N
DeepSMILES: CO[C@H][C@@H][C@]CC[C@@H][C@]6[C@@H][C@@]9O)[C@@]O)C[C@@H][C@H]C[C@@H]9[C@@H]7[C@H]5OC)))))))OC))))))NC8)CC)))))OC)))))COC=O)cccccc6NC=O)C
Scaffold Graph/Node/Bond level: O=C(OCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4NC2)c1ccccc1
Scaffold Graph/Node level: OC(OCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4NC2)C1CCCCC1
Scaffold Graph level: CC(CCC12CCCC34C(CC1)C(CC23)C1CCC2CC1C4C2)C1CCCCC1
Functional groups: cC(=O)OC; COC; cNC(C)=O; CO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
ajacine
External chemical identifiers:
CID:CID_101667972; ZINC:ZINC000072170685; FDASRS:GP3SE3H2BB
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ajacine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 628.76
Log P RDKit 2.09
Topological polar surface area (Å2) RDKit 136.02
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Ajacine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.35
Ajacine
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 High
Log Kp (Skin permeation, cm/s) SwissADME -9.16
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 No
P-glycoprotein substrate SwissADME Yes