Metampicillin (CED0024005)

Record Information

Version

1.0

Creation Date

2026-03-31 20:42:51 UTC

Update Date

2026-08-19 20:17:58 UTC

Accession Number

CHEM057806

Identification

Common Name

Metampicillin

Class

Small Molecule

Description

Metampicillin is an organic compound with the formula C17H19N3O4S1 and an average molecular weight of 361.42 g/mol. Metampicillin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is classified as an organoheterocyclic compound. This substance is found in or released from one recorded source: healthcare, pharmaceuticals & veterinary products (Antibiotics). Recorded exposure routes for this compound include inhalation and oral administration.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-(methylideneamino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6beta-[(2R)-2-(Methylideneamino)-2-phenylacetamido]penicillanic acid	ChEBI
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-(methylideneamino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-[(2R)-2-(Methylideneamino)-2-phenylacetamido]penicillanate	Generator
6b-[(2R)-2-(Methylideneamino)-2-phenylacetamido]penicillanic acid	Generator
6beta-[(2R)-2-(Methylideneamino)-2-phenylacetamido]penicillanate	Generator
6Β-[(2R)-2-(methylideneamino)-2-phenylacetamido]penicillanate	Generator
6Β-[(2R)-2-(methylideneamino)-2-phenylacetamido]penicillanic acid	Generator
Suvipen	MeSH
Methampicillin	MeSH
Methampicillin, calcium salt (2:1), (2S-(2alpha,5alpha,6beta(s*)))-isomer	MeSH
Methampicillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer	MeSH
6-(2-Methyleneamino-2-phenylacetamido)penicillanic acid	MeSH
Magnipen	MeSH
Metakes	MeSH
Serfabiotic	MeSH
Metampicillin sodium	MeSH
Methampicillin, sodium salt	MeSH

Chemical Formula

C₁₇H₁₉N₃O₄S₁

Average Molecular Mass

361.420 g/mol

Monoisotopic Mass

361.110 g/mol

CAS Registry Number

6489-97-0;22232-69-5

IUPAC Name

(2S,5R,6R)-3,3-dimethyl-6-[(2R)-2-(methylideneamino)-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

metampicillin

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N=C)C3=CC=CC=C3)C(=O)N2[C@H]1C(O)=O

InChI Identifier

InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1

InChI Key

FZECHKJQHUVANE-MCYUEQNJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hemithioaminal
Thioether
Imine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:52060 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1.74	ALOGPS
logP	-0.38	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	4.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.87 m³·mol⁻¹	ChemAxon
Polarizability	36.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-014i-2900000000-83eeadfcefc6e1f19d9c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1953000000-d92ae9e630c7ede30878	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02t9-2920000000-87a7fa2c48319613eeaa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066u-8900000000-84c48ff453a9feae384d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0091000000-f9f2fdb808ce545b9a7c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0391000000-fb86b8e6c7494dffb3aa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-016r-9830000000-9c0166c7481bfa26dc39	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
6267.0	Log mg/kg	[3500:11000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
696	Nanotechnology	Industrial manufacturing & chemical processing	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	0.155698
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	79.6398
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	0.233548
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	0.233548
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	82.0531
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	4.7488
Click to view 3D structure	Baculoviral IAP repeat-containing protein 8	Q96P09	Humans	Predicted (SEA)	12.2223
Click to view 3D structure	Baculoviral IAP repeat-containing protein 2	Q13490	Humans	Predicted (SEA)	23.8997
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	0.233548
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	15.1027
Click to view 3D structure	E3 ubiquitin-protein ligase XIAP	P98170	Humans	Predicted (SEA)	78.8613
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	8.71911
Click to view 3D structure	Extended-spectrum beta-lactamase PER-6	D5HSX5	Aeromonas allosaccharophila	Predicted (SEA)	0.856341
Click to view 3D structure	ADC-14 protein	Q0VTR6	Acinetobacter genomosp. 3	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-lactamase SHV-11	Q7X575	Escherichia coli	Predicted (SEA)	0.856341
Click to view 3D structure	ADC-16 protein	Q0VTR8	Acinetobacter genomosp. 3	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	2.10193
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	396.175
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	761.288
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	637.585
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	819.83
Click to view 3D structure	Cathepsin S	P25774	Humans	Predicted (SEA)	862.569
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	2027.27
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	713.644
Click to view 3D structure	Baculoviral IAP repeat-containing protein 3	Q13489	Humans	Predicted (SEA)	55.9736