Penicillanic Acid

HCID 6891CAS 87-53-6

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Basic information

Standard SMILES: CC1(C)S[C@@H]2CC(=O)N2[C@H]1C(=O)O
InChIKey: RBKMMJSQKNKNEV-RITPCOANSA-N
Molecular formula: C8H11NO3S
Average molar mass: 201.25 g/mol
Monoisotopic mass: 201.04596421

Overview

Penicillanic acid is a penam that consists of 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane bearing a carboxy group at position 2 and having (2S,5R)-configuration.

Names & identifiers

Preferred name: Penicillanic Acid
IUPAC: (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
English name: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Molecular formula: C8H11NO3S
Molecular weight: 201.24

Names & synonyms

PENICILLANIC ACID87-53-6PIS09H0QIXAcid, Penicillanic2,2-dimethylpenam-3alpha-carboxylic acidCHEBI:37806DTXSID902360384-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, (2S-cis)-(2S-cis)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidRefChem:170886DTXCID90158529201-750-3

Show more names

penicillanicaci(2S,5β)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid(2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, (2S,5R)-

(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPenicillansaureSulbactam Impurity 9EINECS 201-750-3UNII-PIS09H0QIXSCHEMBL462651PENICILLANIC ACID [MI]CHEMBL325758

Database identifiers

CAS: 87-53-6
PubChem CID: 6891
DTXSID: DTXSID90236038
ChEMBL: CHEMBL325758
ChEBI: CHEBI:37806
UNII: PIS09H0QIX
EC Number: 201-750-3
Nikkaji: J192.646B

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 82.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 13
Formal charge: 0
Complexity: 289

Physicochemical properties

Melting point: 208 · 208-209 °C
Boiling point: 423.8 · 423.8±45.0 °C(Predicted)
Density: 1.46 · 1.46±0.1 g/cm3(Predicted)
solubility: soluble in Water
form: Solid
pka: 2.43 · 2.43±0.50(Predicted)
color: Grey
FDA UNII: 9 H0QIX · PIS09H0QIX

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

Applications

UsesPenicillanic Acid Sodium Salt-d2 is an intermediate in the synthesis of Tazobactam-d4 which is the labeled analog of Tazobactam (T010095), a b-Lactamase inhibitor, used with b-lactam antibiotics to enhance their effect.

Upstream & downstream products

Upstream raw materials

Downstream products

brobactam 6β-Phthalimidopenicillanic Acid

Suppliers17 total

广州佳途科技股份有限公司81960175 18933936954 · [email protected]

南京望知星医药科技有限公司18569809817 · [email protected]

Guangzhou Tosun Pharmaceutical Limited+86-18124244216 +86-18124244216 · [email protected]

陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]

BOC Sciences16314854226 · [email protected]

Additional notes

DefinitionChEBI: A penam that consists of 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane bearing a carboxy group at position 2 and having (2S,5R)-configuration.