IMPPAT Phytochemical information: 
Gagamine
Gagamine
Summary

SMILES: O[C@H]1CC[C@]2(C(=CC[C@@]3([C@@H]2C[C@@H](OC(=O)c2cccnc2)[C@]2([C@]3(O)CC[C@@]2(O)C(O)C)C)O)C1)C
InChI: InChI=1S/C27H37NO7/c1-16(29)25(32)10-11-27(34)24(25,3)21(35-22(31)17-5-4-12-28-15-17)14-20-23(2)8-7-19(30)13-18(23)6-9-26(20,27)33/h4-6,12,15-16,19-21,29-30,32-34H,7-11,13-14H2,1-3H3/t16?,19-,20+,21+,23-,24+,25+,26-,27+/m0/s1
InChIKey: DRPIMPNUZUSUTN-WNCHUELASA-N
DeepSMILES: O[C@H]CC[C@]C=CC[C@@][C@@H]6C[C@@H]OC=O)ccccnc6))))))))[C@][C@]6O)CC[C@@]5O)CO)C))))))C)))))O))))C6))C
Scaffold Graph/Node/Bond level: O=C(OC1CC2C3CCCCC3=CCC2C2CCCC12)c1cccnc1
Scaffold Graph/Node level: OC(OC1CC2C3CCCCC3CCC2C2CCCC12)C1CCCNC1
Scaffold Graph level: CC(CC1CC2C3CCCCC3CCC2C2CCCC12)C1CCCCC1
Functional groups: CO; CC=C(C)C; cC(=O)OC; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Pregnane steroids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Pregnane steroids
Synonymous chemical names:
gagamine, Gagamine
External chemical identifiers:
CID:CID_102005844
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gagamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 487.59
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 140.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Gagamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
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 0.32
Gagamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.69
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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