IMPPAT Phytochemical information: 
Amphibine B
Amphibine B
Summary

SMILES: CC[C@@H]([C@@H](C(=O)N1CC[C@H]2[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N/C=C\c1ccc(O2)cc1)NC(=O)[C@@H](N(C)C)Cc1ccccc1)C
InChI: InChI=1S/C39H47N5O5/c1-5-26(2)34(42-37(46)32(43(3)4)25-29-14-10-7-11-15-29)39(48)44-23-21-33-35(44)38(47)41-31(24-28-12-8-6-9-13-28)36(45)40-22-20-27-16-18-30(49-33)19-17-27/h6-20,22,26,31-35H,5,21,23-25H2,1-4H3,(H,40,45)(H,41,47)(H,42,46)/b22-20-/t26-,31-,32-,33-,34-,35-/m0/s1
InChIKey: BZXBQQGSSIQELG-HVQQJYASSA-N
DeepSMILES: CC[C@@H][C@@H]C=O)NCC[C@H][C@H]5C=O)N[C@@H]Ccccccc6)))))))C=O)N/C=C\ccccO%14)cc6)))))))))))))))))))NC=O)[C@@H]NC)C))Ccccccc6)))))))))))C
Scaffold Graph/Node/Bond level: O=C(CCc1ccccc1)NCC(=O)N1CCC2Oc3ccc(cc3)C=CNC(=O)C(Cc3ccccc3)NC(=O)C21
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCC(O)N1CCC2OC3CCC(CCNC(O)C(CC4CCCCC4)NC(O)C21)CC3
Scaffold Graph level: CC(CCC1CCCCC1)CCC(C)C1CCC2CC3CCC(CCCC(C)C(CC4CCCCC4)CC(C)C21)CC3
Functional groups: CNC(C)=O; CN(C(C)=O)C; CN(C)C; CNC(=O)C; c/C=C\NC(=O)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 b
External chemical identifiers:
CID:CID_5281582; ChEBI:CHEBI:2681; ZINC:ZINC000004098484
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Amphibine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 665.84
Log P RDKit 3.57
Topological polar surface area (Å2) RDKit 120.08
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Amphibine B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.304906
Amphibine B
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 -6.41
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