IMPPAT Phytochemical information: 
Amphibine A
Amphibine A
Summary

SMILES: CC[C@@H]([C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](N(C)C)Cc2c[nH]c3c2cccc3)[C@@H](Oc2ccc(/C=C\NC1=O)cc2)C(C)C)C
InChI: InChI=1S/C33H43N5O4/c1-7-21(4)28-32(40)34-17-16-22-12-14-24(15-13-22)42-30(20(2)3)29(33(41)36-28)37-31(39)27(38(5)6)18-23-19-35-26-11-9-8-10-25(23)26/h8-17,19-21,27-30,35H,7,18H2,1-6H3,(H,34,40)(H,36,41)(H,37,39)/b17-16-/t21-,27-,28-,29-,30-/m0/s1
InChIKey: ZNUMAFXIQXNMMH-UZFRKIFNSA-N
DeepSMILES: CC[C@@H][C@@H]NC=O)[C@@H]NC=O)[C@@H]NC)C))Ccc[nH]cc5cccc6)))))))))))))[C@@H]Occcc/C=C\NC%14=O)))))cc6)))))))CC)C)))))))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)C(NC(=O)CCc2c[nH]c3ccccc23)COc2ccc(cc2)C=CN1
Scaffold Graph/Node level: OC1CNC(O)C(NC(O)CCC2CNC3CCCCC23)COC2CCC(CCN1)CC2
Scaffold Graph level: CC1CCCC2CCC(CC2)CCC(CC(C)CCC2CCC3CCCCC32)C(C)CC1
Functional groups: c/C=C\NC(=O)C; CNC(=O)C; CNC(C)=O; CN(C)C; c[nH]c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids|Amino acids and Peptides
NP Classifier Superclass: Peptide alkaloids
NP Classifier Class: Ansa peptide alkaloids
Synonymous chemical names:
amphibine a
External chemical identifiers:
CID:CID_5281581; ChEBI:CHEBI:2680; ZINC:ZINC000004098483
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Amphibine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 573.74
Log P RDKit 3.86
Topological polar surface area (Å2) RDKit 115.56
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Amphibine A
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 Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.33
Amphibine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.99
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