IMPPAT Phytochemical information: 
(2S,3S)-2-(dimethylamino)-3-methyl-N-[(3R,4S,7S,10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
(2S,3S)-2-(dimethylamino)-3-methyl-N-[(3R,4S,7S,10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
Summary

SMILES: CC[C@@H]([C@@H](C(=O)N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N/C=C\c2ccc(O[C@@H]1C(C)C)cc2)N(C)C)C
InChI: InChI=1S/C28H44N4O4/c1-9-19(6)24(32(7)8)28(35)31-23-25(18(4)5)36-21-12-10-20(11-13-21)14-15-29-26(33)22(16-17(2)3)30-27(23)34/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,33)(H,30,34)(H,31,35)/b15-14-/t19-,22-,23-,24-,25+/m0/s1
InChIKey: ULQXKOIGVXLOOC-TYCDZCMWSA-N
DeepSMILES: CC[C@@H][C@@H]C=O)N[C@@H]C=O)N[C@@H]CCC)C)))C=O)N/C=C\ccccO[C@@H]%14CC)C))))cc6))))))))))))))))NC)C)))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)CCOc2ccc(cc2)C=CN1
Scaffold Graph/Node level: OC1CCOC2CCC(CCNC(O)CN1)CC2
Scaffold Graph level: CC1CCCC2CCC(CCCC(C)CC1)CC2
Functional groups: CN(C)C; CNC(C)=O; 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:
frangulanine
External chemical identifiers:
CID:CID_101967141
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3S)-2-(dimethylamino)-3-methyl-N-[(3R,4S,7S,10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 500.68
Log P RDKit 3.18
Topological polar surface area (Å2) RDKit 99.77
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.61
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
(2S,3S)-2-(dimethylamino)-3-methyl-N-[(3R,4S,7S,10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
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 0.51
(2S,3S)-2-(dimethylamino)-3-methyl-N-[(3R,4S,7S,10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.82
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