IMPPAT Phytochemical information: 
Methyl acetoacetate

Methyl acetoacetate
Summary

SMILES: COC(=O)CC(=O)C
InChI: InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
InChIKey: WRQNANDWMGAFTP-UHFFFAOYSA-N
DeepSMILES: COC=O)CC=O)C
Functional groups: COC(C)=O; CC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Keto acids and derivatives
ClassyFire Subclass: Beta-keto acids and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates
NP Classifier Class: Oxo fatty acids
Synonymous chemical names:
acetoacetic acid methyl ester
External chemical identifiers:
CID:CID_7757; ChEMBL:CHEMBL3186053; ChEBI:CHEBI:166454; ZINC:ZINC000005159232; FDASRS:CW4I82QAX1; SureChEMBL:SCHEMBL1162; MolPort-001-789-977
Chemical structure download


Methyl acetoacetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 116.12
Log P RDKit 0.14
Topological polar surface area (Å2) RDKit 43.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 5
Number of heavy atoms RDKit 8
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
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 0


Methyl acetoacetate
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 3
Ghose filter RDKit Failed
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 0.380402


Methyl acetoacetate
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 -7.03
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