ChemFOnt: Showing chemical card for 6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CFc000228205)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:53:54 UTC

Chemfont ID

CFc000228205

Molecule Identification

Common Name

6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Definition

6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, also known as N(4)-methyl-D-asparaginylamoxicillin, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on 6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
N(4)-Methyl-D-asparaginylamoxicillin	MeSH

Chemical Formula

C₂₁H₂₇N₅O₇S

Average Molecular Weight

493.54

Monoisotopic Molecular Weight

493.163119403

IUPAC Name

6-{2-[2-amino-3-(methylcarbamoyl)propanamido]-2-(4-hydroxyphenyl)acetamido}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

6-{2-[2-amino-3-(methylcarbamoyl)propanamido]-2-(4-hydroxyphenyl)acetamido}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CNC(=O)CC(N)C(=O)NC(C(=O)NC1C2SC(C)(C)C(N2C1=O)C(O)=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)

InChI Key

BHELIUBJHYAEDK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Penicillin
Asparagine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Penam
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Fatty acyl
Benzenoid
Thiazolidine
Tertiary carboxylic acid amide
Beta-lactam
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Azetidine
Carboxamide group
Lactam
Thioether
Organoheterocyclic compound
Azacycle
Dialkylthioether
Hemithioaminal
Monocarboxylic acid or derivatives
Carboxylic acid
Primary amine
Organic oxygen compound
Primary aliphatic amine
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	0.59	ALOGPS
logP	-4.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	119.56 m³·mol⁻¹	ChemAxon
Polarizability	48.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0248670

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2245

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CFc000228205)

MOL for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for CFc000228205 (6-[[2-[[2-Amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)