temocillin - Moligand™ , Bacterial penicillin-binding protein inhibitor, CAS No.66148-78-5, Bacterial penicillin-binding protein inhibitor

CAS: 66148-78-5 Cat. No.: T614377 Formula: C₁₆H₁₈N₂O₇S₂ Molecular Weight: 414.5 PubChem CID: 171758

GRADE & PURITY Moligand™

Synonyms

(2S,5R,6S)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|TEMOCILLIN [MI]|Temocillinum|(2S,5R,6S)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|TEMOCILLIN [INN]|Temocillina|Temocilline|4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((CARBOXY-3-THIENYLACETYL)AMINO)-6-METHOXY-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.ALPHA.))-|BRL 17421|Temocillin [USAN:INN:BAN]|Ethyl 2-(benzoyl-3,4-dichloroanilino)propanoate #|Temocillinum [INN-Latin]|N-((2S,5R,6S)-2-Carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-3-thiophenemalonamic acid|Temocillina [INN-Spanish]|Temocillin|TEMOCILLIN [WHO-DD]|(2S,5R,6S)-6-[(3-hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|BRL 17421 FREE ACID|Temocillin (USAN)|BRL 17421 [as sodium]|(2S,5R,6S)-6-[2-carboxy(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|BRL17421|BRL-17421|BRL-17421 FREE ACID|(2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|(2S,5R,6S)-6-[2-carboxy-2-(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|Temocilline [INN-French]|N-[(2S,5R,6S)-2-Carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-3-thiophenemalonamic acid|TEMOCILLIN [MART.]|Bromocriptina (INN-Spanish)|4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6alpha))-|(2S,5R,6S)-6-(2-carboxy-2-(thiophen-3-yl)acetamido)-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|TEMOCILLIN [USAN]|BROMOCRIPTINE MESYLATE (USP-RS)|(1s,3s,5r)-3-tropyloxy-8-isopropyltropaniumbromide|Negaban

Storage

Room temperature

Specifications

Synonyms

(2S,5R,6S)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | TEMOCILLIN [MI] | Temocillinum | (2S,5R,6S)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | TEMOCILLIN [INN] | Temocillina | Temocillin Show more

Specifications & Purity

Moligand™

Storage

Room temperature

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Bacterial penicillin-binding protein inhibitor

Product Properties

alogp

1.1

Names and Identifiers

Canonical Smiles

CO[C@@]1(NC(=O)C(c2cscc2)C(=O)O)C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C

IUPAC Name

(2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

InChIKey

BVCKFLJARNKCSS-DWPRYXJFSA-N

INCHI

1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1

Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@](C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C

PubChem CID

171758

Molecular Weight

414.5

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Penicillins N-acyl-alpha amino acids and derivatives 1,3-dicarbonyl compounds Dicarboxylic acids and derivatives Thiophenes Thiazolidines Tertiary carboxylic acid amides Heteroaromatic compounds Secondary carboxylic acid amides Azetidines Thiohemiaminal derivatives Azacyclic compounds Carboxylic acids Dialkylthioethers Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-dipeptide - Penicillin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Penam - Dicarboxylic acid or derivatives - 1,3-dicarbonyl compound - Beta-lactam - Tertiary carboxylic acid amide - Thiazolidine - Thiophene - Heteroaromatic compound - Azetidine - Secondary carboxylic acid amide - Carboxamide group - Lactam - Hemithioaminal - Thioether - Azacycle - Organoheterocyclic compound - Dialkylthioether - Carboxylic acid - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: penicillin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Klebsiella pneumoniae (43867 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Beta-lactamase L1 (242 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Chryseobacterium indologenes (25 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pectobacterium atrosepticum (15 Activities)

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Serum (58 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 414.500 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 414.056 Da
• Monoisotopic Mass: 414.056 Da
• Topological Polar Surface Area: 187.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 700.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 66148-78-5, the molecular formula is C16H18N2O7S2, and the molecular weight is 414.5 g/mol. InChIKey BVCKFLJARNKCSS-DWPRYXJFSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.