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sarecycline   Click here for help

GtoPdb Ligand ID: 12921

Synonyms: P005672 | Seysara®
Approved drug PDB Ligand
sarecycline is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Sarecycline is a tetracycline antibacterial with narrow-spectrum activity that was developed as an oral anti-acne therapeutic. Note that the structure shown here matches the CAS-assigned structure and is the same as the ChEMBL entry linked to below. The PubChem standardized chemical structure (CID 54681908) for sarecycline is represented with slightly different stereochemistry.
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 9
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 173.86
Molecular weight 487.5
XLogP -0.51
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)[C@H]1[C@]2([H])C[C@]3([H])CC4=C(C(=CC=C4CN(C)OC)O)C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O
Isomeric SMILES O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)(C[C@]3(C(=C2O)C(=O)C=4C(C3)=C(CN(OC)C)C=CC4O)[H])[H]
InChI InChI=1S/C24H29N3O8/c1-26(2)18-13-8-11-7-12-10(9-27(3)35-4)5-6-14(28)16(12)19(29)15(11)21(31)24(13,34)22(32)17(20(18)30)23(25)33/h5-6,11,13,18,28,30-31,34H,7-9H2,1-4H3,(H2,25,33)/t11-,13-,18-,24-/m0/s1
InChI Key PQJQFLNBMSCUSH-SBAJWEJLSA-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. US FDA (2018)
IUPAC Name Click here for help
(4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-{[methoxy(methyl)amino]methyl}-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9743 sarecycline
Synonyms Click here for help
P005672 | Seysara®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Seysara (Sarecycline)
Other databases
CAS Registry No. 1035654-66-0 (source: Scifinder)
ChEMBL Ligand CHEMBL2364632
DrugBank Ligand DB12035
DrugCentral Ligand 5298
GtoPdb PubChem SID 485206042
PubChem CID 54681908
RCSB PDB Ligand V7A
Search Google for chemical match using the InChIKey PQJQFLNBMSCUSH-SBAJWEJLSA-N
Search Google for chemicals with the same backbone PQJQFLNBMSCUSH
Search PubMed clinical trials sarecycline
Search PubMed titles sarecycline
Search PubMed titles/abstracts sarecycline
UniChem Compound Search for chemical match using the InChIKey PQJQFLNBMSCUSH-SBAJWEJLSA-N
UniChem Connectivity Search for chemical match using the InChIKey PQJQFLNBMSCUSH-SBAJWEJLSA-N