IMPPAT Phytochemical information: 
(4S,5R,6R)-6-hydroxy-4,5-dimethyl-2-oxo-1,4,5,6-tetrahydropyrrolo[1,2-d][1,4]oxazocine-9-carbaldehyde
(4S,5R,6R)-6-hydroxy-4,5-dimethyl-2-oxo-1,4,5,6-tetrahydropyrrolo[1,2-d][1,4]oxazocine-9-carbaldehyde
Summary

SMILES: C[C@@H]1[C@@H](O)c2ccc(n2CC(=O)O[C@H]1C)C=O
InChI: InChI=1S/C12H15NO4/c1-7-8(2)17-11(15)5-13-9(6-14)3-4-10(13)12(7)16/h3-4,6-8,12,16H,5H2,1-2H3/t7-,8-,12+/m0/s1
InChIKey: BJGONNCLQGPBIC-YVZVNANGSA-N
DeepSMILES: C[C@@H][C@@H]O)ccccn5CC=O)O[C@H]%11C))))))C=O
Scaffold Graph/Node/Bond level: O=C1Cn2cccc2CCCO1
Scaffold Graph/Node level: OC1CN2CCCC2CCCO1
Scaffold Graph level: CC1CCCCC2CCCC2C1
Functional groups: CO; cn(c)C; CC(=O)OC; cC=O
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|Polyketides
Synonymous chemical names:
desmodimine
External chemical identifiers:
CID:CID_192463
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(4S,5R,6R)-6-hydroxy-4,5-dimethyl-2-oxo-1,4,5,6-tetrahydropyrrolo[1,2-d][1,4]oxazocine-9-carbaldehyde
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 237.26
Log P RDKit 0.92
Topological polar surface area (Å2) RDKit 68.53
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
(4S,5R,6R)-6-hydroxy-4,5-dimethyl-2-oxo-1,4,5,6-tetrahydropyrrolo[1,2-d][1,4]oxazocine-9-carbaldehyde
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.582107
(4S,5R,6R)-6-hydroxy-4,5-dimethyl-2-oxo-1,4,5,6-tetrahydropyrrolo[1,2-d][1,4]oxazocine-9-carbaldehyde
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.27
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 No