Ampicillin trihydrate - analytical standard, Moligand™ , CAS No.7177-48-2

CAS: 7177-48-2 Cat. No.: A102050 Formula: C₁₆H₁₉N₃O₄S·3H₂O Molecular Weight: 403.45 EC Number: 615-347-9

GRADE & PURITY Analytical standard, Moligand™

Synonyms

CHEBI:31209 | Amcill (TN) | HMS2095G10 | AMPICILLIN TRIHYDRATE [WHO-IP] | Cymbi | MFCD00072036 | Ampicillin hydrate | AMPICILLIN TRIHYDRATE [WHO-DD] | Ampicillin hydrate (JP17) | AMPICILLIN TRIHYDRATE [EP MONOGRAPH] | D-(-)--Aminobenzylpenicillin (trihydr

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

CHEBI:31209 | Amcill (TN) | HMS2095G10 | AMPICILLIN TRIHYDRATE [WHO-IP] | Cymbi | MFCD00072036 | Ampicillin hydrate | AMPICILLIN TRIHYDRATE [WHO-DD] | Ampicillin hydrate (JP17) | AMPICILLIN TRIHYDRATE [EP MONOGRAPH] | D-(-)--Aminobenzylpenicillin (trihydr

Specifications & Purity

analytical standard, Moligand™

Biochemical and Physiological Mechanisms

β-lactam antibiotic (MIC 50 = 3.12 μg/ml). Competitively inhibits transpeptidase causing cell wall disruption to Gram-positive and Gram-negative bacteria. Active in vitro and in vivo .

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard, Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

Pubchem Sid

508814158

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/508814158

Canonical Smiles

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C.O.O.O

IUPAC Name

(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;trihydrate

InChIKey

RXDALBZNGVATNY-CWLIKTDRSA-N

INCHI

1S/C16H19N3O4S.3H2O/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;;;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);3*1H2/t9-,10-,11+,14-;;;/m1.../s1

Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C.O.O.O

Alternate CAS

69-53-4

Molecular Weight

403.45

Reaxy-Rn

54277913

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=54277913&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Lactams
      • Subclass Beta lactams
        • Level5 Penams
          • Level6 Penicillins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Lactams
• Subclass: Beta lactams
• Intermediate Tree Nodes: Penams
• Direct Parent: Penicillins
• Alternative Parents: N-acyl-alpha amino acids and derivatives Alpha amino acid amides Phenylacetamides Aralkylamines Thiazolidines Tertiary carboxylic acid amides Secondary carboxylic acid amides Amino acids Azetidines Thiohemiaminal derivatives Monocarboxylic acids and derivatives Azacyclic compounds Dialkylthioethers Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Penicillin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - Phenylacetamide - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Thiazolidine - Tertiary carboxylic acid amide - Amino acid or derivatives - Azetidine - Amino acid - Carboxamide group - Secondary carboxylic acid amide - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Dialkylthioether - Hemithioaminal - Thioether - Primary aliphatic amine - Amine - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Primary amine - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound 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].
• External Descriptors: hydrate

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(Human)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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Streptococcus viridans (303 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Proteus mirabilis (3894 Activities)

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Bacillus subtilis (32866 Activities)

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Bacillus spizizenii (1898 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture sensitive; Light sensitive
• Specific Rotation[α]: 293° (C=0.5,H2O)
• Melt Point(°C): 198-200°C
• Molecular Weight: 403.500 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 403.141 Da
• Monoisotopic Mass: 403.141 Da
• Topological Polar Surface Area: 141.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 562.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 4

XLogP3