Atosiban (CED0008356)

Record Information

Version

1.0

Creation Date

2016-05-22 06:55:06 UTC

Update Date

2026-08-22 14:34:45 UTC

Accession Number

CHEM020206

Identification

Common Name

Atosiban

Class

Small Molecule

Description

Atosiban is an organic compound with the chemical formula C43H67N11O12S2. Atosiban belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 994.19 g/mol, Atosiban is a heavy molecule. The compound is recorded as being found in or released from two sources: electrical and electronic equipment antennas, and gynecological pharmaceuticals and veterinary products. The recorded route of exposure for this substance is intravenous. Atosiban acts upon four recorded protein targets, serving as an antagonist of the oxytocin receptor (OXTR), the vasopressin V1a receptor (AVPR1A), the vasopressin V1b receptor (AVPR1B), and the vasopressin V2 receptor (AVPR2).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-5-Amino-2-({[(2S)-1-[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-6,9,12,15,18-pentahydroxy-7-[(C-hydroxycarbonimidoyl)methyl]-10-[(1R)-1-hydroxyethyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-N-[(C-hydroxycarbonimidoyl)methyl]pentanimidate	Generator
1-deamino-2-Tyr(oet)-4-THR-8-orn-oxytocin	MeSH
(Mpa(1),D-tyr(et)2,THR(4),orn(8))oxytocin	MeSH
(Mpa(1)-D-tyr(et)(2)-THR(4)-orn(8))-oxytocin	MeSH
Atosiban	MeSH

Chemical Formula

C₄₃H₆₇N₁₁O₁₂S₂

Average Molecular Mass

994.190 g/mol

Monoisotopic Mass

993.441 g/mol

CAS Registry Number

90779-69-4

IUPAC Name

(2S)-5-amino-2-({[(2S)-1-[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-6,9,12,15,18-pentahydroxy-7-[(C-hydroxycarbonimidoyl)methyl]-10-[(1R)-1-hydroxyethyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-N-[(C-hydroxycarbonimidoyl)methyl]pentanimidic acid

Traditional Name

atosiban

SMILES

[H][C@](C)(O)[C@]1([H])N=C(O)[C@@]([H])(N=C(O)[C@@]([H])(CC2=CC=C(OCC)C=C2)N=C(O)CCSSC[C@]([H])(N=C(O)[C@]([H])(CC(O)=N)N=C1O)C(=O)N1CCC[C@@]1([H])C(O)=N[C@@]([H])(CCCN)C(O)=NCC(O)=N)[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C43H67N11O12S2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1

InChI Key

VWXRQYYUEIYXCZ-OBIMUBPZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

Thia fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic transition metal salt
Organic alkali metal salt
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organic oxide
Carbonyl group
Organic salt
Organic sodium salt
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	0.065 g/L	ALOGPS
logP	1.28	ALOGPS
logP	0.19	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.78	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	392.08 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	276.15 m³·mol⁻¹	ChemAxon
Polarizability	102.62 Å³	ChemAxon
Number of Rings	3	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	splash10-05dj-4202040009-824b60c982cd25cc9c2d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9100001002-73237722147477e25123	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-7935000000-2478edd16a347f41e0b8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-0000323009-f7d6a238de3049a95f32	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-007o-3211122009-919201da08018c06ab68	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0084-4972202342-6e884d2e072d0cd848a1	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
316	Gynecologicals	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Atosiban Drug Metabolism Action Pathway

Atosiban Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Vasopressin V2 receptor	Q00788	Rattus norvegicus	Predicted (SEA)	132.966
Click to view 3D structure	Vasopressin V1a receptor	P30560	Rattus norvegicus	Predicted (SEA)	123.702
Click to view 3D structure	Oxytocin receptor	P30559	Humans	Predicted (SEA)	134.056
Click to view 3D structure	Vasopressin V2 receptor	P30518	Humans	Predicted (SEA)	127.984
Click to view 3D structure	Vasopressin V1b receptor	P47901	Humans	Predicted (SEA)	114.75
Click to view 3D structure	Vasopressin V1a receptor	P37288	Humans	Predicted (SEA)	190.341
Click to view 3D structure	Vasopressin V1b receptor	P48974	Rattus norvegicus	Predicted (SEA)	99.0242
Click to view 3D structure	Oxytocin receptor	P70536	Rattus norvegicus	Predicted (SEA)	126.427
Click to view 3D structure	Vasopressin V2 receptor	P32307	Sus scrofa	Predicted (SEA)	82.9873
Click to view 3D structure	Serine protease 1	P00760	Bos taurus	Predicted (SEA)	498.936
Click to view 3D structure	Envelope glycoprotein gp160	P19550	Human immunodeficiency virus type 1 group M subtype B (isolate SF162)(HIV-1)	Predicted (SEA)	76.6815
Click to view 3D structure	Trypsin-3	P35030	Humans	Predicted (SEA)	77.3821
Click to view 3D structure	Cathepsin G	P08311	Humans	Predicted (SEA)	408.319
Click to view 3D structure	C5a anaphylatoxin chemotactic receptor 1	P30993	Mus musculus	Predicted (SEA)	244.213
Click to view 3D structure	T-cell surface antigen CD2	P06729	Humans	Predicted (SEA)	59.0876
Click to view 3D structure	Plasminogen	P00747	Humans	Predicted (SEA)	1313.39
Click to view 3D structure	Telomeric repeat-binding factor 2	Q15554	Humans	Predicted (SEA)	189.874
Click to view 3D structure	Suppressor of tumorigenicity 14 protein	Q9Y5Y6	Humans	Predicted (SEA)	681.336
Click to view 3D structure	Serine protease 1	P07477	Humans	Predicted (SEA)	1107.02
Click to view 3D structure	Kallikrein-7	P49862	Humans	Predicted (SEA)	137.326
Click to view 3D structure	Neurotensin receptor type 1	O88319	Mus musculus	Predicted (SEA)	216.421
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	2606.16
Click to view 3D structure	Neurotensin receptor type 1	P30989	Humans	Predicted (SEA)	514.583
Click to view 3D structure	Adapter molecule crk	P46108	Humans	Predicted (SEA)	195.791
Click to view 3D structure	Neurotensin receptor type 1	P20789	Rattus norvegicus	Predicted (SEA)	214.864