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spectinomycin   Click here for help

GtoPdb Ligand ID: 11127

Synonyms: actinospectacin | M-141 | Trobicin® | U-18409 | U-18409E | U18409
Approved drug PDB Ligand
spectinomycin is an approved drug
Compound class: Natural product
Comment: Spectinomycin is an aminocyclitol aminoglycoside bacteriostatic antibacterial. It was isolated from Streptomyces spectabilis. Spectinomycin is active against gram-negative bacteria.
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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Click here for structure editor
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 9
Hydrogen bond donors 5
Rotatable bonds 2
Topological polar surface area 129.51
Molecular weight 332.16
XLogP -1.91
No. Lipinski's rules broken 0

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 CN[C@H]1[C@H](O)[C@H]2O[C@@H]3O[C@H](C)CC(=O)[C@@]3(O[C@@H]2[C@H]([C@H]1O)NC)O
Isomeric SMILES CN[C@H]1[C@H](O)[C@H]2O[C@@H]3O[C@H](C)CC(=O)[C@@]3(O[C@@H]2[C@H]([C@H]1O)NC)O
InChI InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1
InChI Key UNFWWIHTNXNPBV-WXKVUWSESA-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 Natural product
Approved drug? Yes.
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
International Nonproprietary Names Click here for help
INN number INN
1429 spectinomycin
Synonyms Click here for help
actinospectacin | M-141 | Trobicin® | U-18409 | U-18409E | U18409
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Spectinomycin
Other databases
CAS Registry No. 1695-77-8 (source: PubChem)
ChEBI CHEBI:9215
ChEMBL Ligand CHEMBL1167
DrugBank Target DB00919
DrugCentral Ligand 2468
GtoPdb PubChem SID 434122187
PubChem CID 15541
RCSB PDB Ligand SCM
Search Google for chemical match using the InChIKey UNFWWIHTNXNPBV-WXKVUWSESA-N
Search Google for chemicals with the same backbone UNFWWIHTNXNPBV
Search PubMed clinical trials spectinomycin
Search PubMed titles spectinomycin
Search PubMed titles/abstracts spectinomycin
UniChem Compound Search for chemical match using the InChIKey UNFWWIHTNXNPBV-WXKVUWSESA-N
UniChem Connectivity Search for chemical match using the InChIKey UNFWWIHTNXNPBV-WXKVUWSESA-N