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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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (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
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UniChem Compound Search for chemical match using the InChIKey PQJQFLNBMSCUSH-SBAJWEJLSA-N
UniChem Connectivity Search for chemical match using the InChIKey PQJQFLNBMSCUSH-SBAJWEJLSA-N