rolitetracycline   Click here for help

GtoPdb Ligand ID: 12760

Synonyms: pyrrolidinylmethyltetracycline | Reverin® | SQ 15,659 | Syntetrin® | Velacycline®
Approved drug
rolitetracycline is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Rolitetracycline is a parenterally delivered prodrug of tetracycline, an antibacterial that has activity against Gram-negative and Gram-positive bacteria.
Note that the structure shown here matches the CAS-assigned structure and is the same as the ChEBI and ChEMBL entries linked to below. There is no exact match in PubChem for the structure shown here.

rolitetracycline is commercially available from our sponsors

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 11
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 170.87
Molecular weight 527.57
XLogP 0.22
No. Lipinski's rules broken 3

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 C[C@]1(C2=CC=CC(=C2C(=O)C3=C([C@]4([C@@]([H])(C[C@@]31[H])[C@@H](C(=C(C4=O)C(=O)NCN5CCCC5)O)N(C)C)O)O)O)O
Isomeric SMILES [H][C@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCN5CCCC5)=C(O)[C@H]2N(C)C
InChI InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1
InChI Key HMEYVGGHISAPJR-IAHYZSEUSA-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. FDA (1959)
Withdrawn drug? Yes
Is prodrug? Yes
Active form tetracycline
IUPAC Name Click here for help
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-[(pyrrolidin-1-yl)methyl]-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1041 rolitetracycline
Synonyms Click here for help
pyrrolidinylmethyltetracycline | Reverin® | SQ 15,659 | Syntetrin® | Velacycline®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rolitetracycline
Other databases
BindingDB Ligand 50477463
CAS Registry No. 751-97-3 (source: Scifinder)
ChEBI CHEBI:63334
ChEMBL Ligand CHEMBL1237046
DrugBank Ligand DB01301
DrugCentral Ligand 2399
GtoPdb PubChem SID 483123308
PubChem CID 54682938
Search Google for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N
Search Google for chemicals with the same backbone HMEYVGGHISAPJR
Search PubMed clinical trials rolitetracycline
Search PubMed titles rolitetracycline
Search PubMed titles/abstracts rolitetracycline
UniChem Compound Search for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N
UniChem Connectivity Search for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N

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MedChemExpress
Rolitetracycline (links to external site)
Cat. No. HY-18257