carumonam   Click here for help

GtoPdb Ligand ID: 12296

Synonyms: AMA-1080 | Ro 17-2301
Approved drug
carumonam is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Carumonam is a monocyclic β-lactam (monobactam) antibacterial compound. It is the result of modification of the natural product sulfazecin [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 290.52
Molecular weight 466.02
XLogP -3.17
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)OC[C@@H]1[C@H](NC(=O)/C(=N\OCC(=O)O)/c2csc(n2)N)C(=O)N1S(=O)(=O)O
Isomeric SMILES c1c(nc(s1)N)/C(=N/OCC(=O)O)/C(=O)N[C@H]1[C@H](N(C1=O)S(=O)(=O)O)COC(=O)N
InChI InChI=1S/C12H14N6O10S2/c13-11-15-4(3-29-11)7(17-28-2-6(19)20)9(21)16-8-5(1-27-12(14)23)18(10(8)22)30(24,25)26/h3,5,8H,1-2H2,(H2,13,15)(H2,14,23)(H,16,21)(H,19,20)(H,24,25,26)/b17-7-/t5-,8+/m1/s1
InChI Key UIMOJFJSJSIGLV-JNHMLNOCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Japan (0)
IUPAC Name Click here for help
2-[[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-(carbamoyloxymethyl)-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxyacetic acid
International Nonproprietary Names Click here for help
INN number INN
5508 carumonam
Synonyms Click here for help
AMA-1080 | Ro 17-2301
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Carumonam
Other databases
CAS Registry No. 87638-04-8 (source: Scifinder)
ChEBI CHEBI:55486
ChEMBL Ligand CHEMBL1614658
DrugBank Ligand DB13553
DrugCentral Ligand 521
GtoPdb PubChem SID 479821087
PubChem CID 6540466
Search Google for chemical match using the InChIKey UIMOJFJSJSIGLV-JNHMLNOCSA-N
Search Google for chemicals with the same backbone UIMOJFJSJSIGLV
Search PubMed clinical trials carumonam
Search PubMed titles carumonam
Search PubMed titles/abstracts carumonam
UniChem Compound Search for chemical match using the InChIKey UIMOJFJSJSIGLV-JNHMLNOCSA-N
UniChem Connectivity Search for chemical match using the InChIKey UIMOJFJSJSIGLV-JNHMLNOCSA-N