Quinupristin (CED0004968)

Record Information

Version

1.0

Creation Date

2016-05-25 18:27:13 UTC

Update Date

2026-05-14 16:59:53 UTC

Accession Number

CHEM022298

Identification

Common Name

Quinupristin

Class

Small Molecule

Description

Quinupristin is an organic compound with the chemical formula C53H67N9O10S. Quinupristin belongs to the depsipeptides, a subclass of peptidomimetics within the organic compounds. With an average molecular weight of 1,022 g/mol, Quinupristin is a heavy molecule. This compound is found in or released from healthcare, pharmaceuticals, and veterinary products used as antibiotics. Recorded exposure routes for the substance include inhalation and oral administration. In terms of biological activity, Quinupristin acts as an inhibitor of two protein targets: Large ribosomal subunit protein uL10 (rplJ) and Large ribosomal subunit protein uL22 (rplV).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5DElta-(3-quinuclidinyl)thiomethylpristinamycin ia	HMDB

Chemical Formula

C₅₃H₆₇N₉O₁₀S

Average Molecular Mass

1022.218 g/mol

Monoisotopic Mass

1021.473 g/mol

CAS Registry Number

120138-50-3

IUPAC Name

N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide

Traditional Name

quinupristin

SMILES

CC[C@H]1NC(=O)[C@@H](NC(=O)C2=NC=CC=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)C2CC(=O)C(CS[C@@H]3CN4CCC3CC4)CN2C(=O)[C@H](CC2=CC=C(C=C2)N(C)C)N(C)C(=O)[C@@H]2CCCN2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35?,37-,38+,39?,40+,43-,44+,45+/m1/s1

InChI Key

WTHRRGMBUAHGNI-MJWHERSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid ester
Macrolactam
Alpha-amino acid or derivatives
Pyridine carboxylic acid or derivatives
Pyridinecarboxamide
2-heteroaryl carboxamide
Aniline or substituted anilines
Dialkylarylamine
Quinuclidine
Tertiary aliphatic/aromatic amine
Piperidinone
Hydroxypyridine
Monocyclic benzene moiety
Piperidine
Benzenoid
Pyridine
Vinylogous acid
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Ketone
Lactam
Lactone
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Thioether
Sulfenyl compound
Dialkylthioether
Organoheterocyclic compound
Amine
Organic oxide
Organooxygen compound
Organosulfur compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclodepsipeptide (CHEBI:8732 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.18	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	8.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	231.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	272.84 m³·mol⁻¹	ChemAxon
Polarizability	107.02 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0c00-6970000181-0021de1f1b30de2483f9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h4o-2920000022-e4668837cc5c1097a5c6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fb9-3892312000-c8bc1d8139f72acffaba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-1952020010-0842fbe50825cbb08da5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-1910000011-7462578de298c38c44e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0900100000-b123fe4501640b802cd1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9100000001-eaa02d5f171652e68468	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9500000012-190a4b6a9e83296377d6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-9300000125-1464978e45207a6789af	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9000000001-7f4cef8f5acead1cb1a3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9400000014-979b65d16b1acb016f95	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-7900000000-e4ef6350037b608e09ad	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Quinupristin Action Pathway

Quinupristin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Growth factor receptor-bound protein 2	Q60631	Mus musculus	Predicted (SEA)	0.233548
Click to view 3D structure	Aureobasidin-resistance protein	Q9Y745	Neosartorya fumigata (Aspergillus fumigatus)	Predicted (SEA)	7.94062
Click to view 3D structure	Melanocortin receptor 4	P56450	Mus musculus	Predicted (SEA)	227.475
Click to view 3D structure	T-cell surface antigen CD2	P06729	Humans	Predicted (SEA)	42.9728
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	932.945
Click to view 3D structure	Inducible T-cell costimulator	Q9Y6W8	Humans	Predicted (SEA)	61.7344
Click to view 3D structure	Melanocortin receptor 3	P33033	Mus musculus	Predicted (SEA)	239.386
Click to view 3D structure	Plasminogen	P00747	Humans	Predicted (SEA)	660.317
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	1888.47
Click to view 3D structure	Proprotein convertase subtilisin/kexin type 9	Q80W65	Mus musculus	Predicted (SEA)	59.3211
Click to view 3D structure	Cathepsin G	P08311	Humans	Predicted (SEA)	201.552
Click to view 3D structure	Nicotinamide N-methyltransferase	O55239	Mus musculus	Predicted (SEA)	47.488
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	707.727
Click to view 3D structure	Kallikrein-7	P49862	Humans	Predicted (SEA)	73.8011
Click to view 3D structure	Neutrophil elastase	P08246	Humans	Predicted (SEA)	297.851
Click to view 3D structure	Melanocortin receptor 4	P32245	Humans	Predicted (SEA)	419.763
Click to view 3D structure	Myeloblastin	P24158	Humans	Predicted (SEA)	50.057
Click to view 3D structure	Coagulation factor XI	P03951	Humans	Predicted (SEA)	462.424
Click to view 3D structure	Endothelin-1 receptor	P25101	Humans	Predicted (SEA)	260.25
Click to view 3D structure	Serine protease 1	P00760	Bos taurus	Predicted (SEA)	446.232
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	2188.81
Click to view 3D structure	EH domain-containing protein 1	Q9H4M9	Humans	Predicted (SEA)	40.248
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	594.534
Click to view 3D structure	Plasma kallikrein	P03952	Humans	Predicted (SEA)	837.969
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	1885.9