(2S)-5-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-7-(carbamoylmethyl)-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 153910
• Molecular Formular: C43H67N11O12S2
• Molecular Mass: 994.18858
• Monoisotopic Mass: 993.44120864
• SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N1)Cc1ccc(cc1)OCC)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)[C@@H](C)O
• Canonical SMILES: NCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSCCC(=O)N[C@@H](Cc2ccc(cc2)OCC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N1)CC(=O)N)[C@H](O)C)[C@H](CC)C
• InChI: 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
• InChIKey: VWXRQYYUEIYXCZ-OBIMUBPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-7-(carbamoylmethyl)-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: atosiban
• Synonyms: 1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin; 1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin; Tractocile; Atosiban

Database IDs

• CAS Number: 90779-69-4
• MDL Number: MFCD00672436
• PubChem SID: 24724390; 162248049
• PubChem CID: 5311010

CALCULATED PROPERTIES

• Acid pKa: 11.276109
• H Acceptors: 13
• H Donor: 11
• LogD (pH = 5.5): -7.604245
• LogD (pH = 7.4): -6.751657
• Log P: -4.606656
• Molar Refractivity: 250.6237 cm^3
• Polarizability: 98.38658 Å^3
• Polar Surface Area: 365.67 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≤100 mg/mL
• Apperance: semisolid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... AVPR1A(552), OXTR(5021)rat ... Oxtr(25342)

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C43H67N11O12S2

DETAILS

Sigma Aldrich - A3480

Biochem/physiol Actions
Atosiban is a peptide oxytocin receptor antagonist.
Reconstitution
Reconstitute in deionized water at not less than 100 μg/mL, which can then be diluted into aqueous vehicle of choice. Solutions may be stored at 2-8 °C for up to seven days. For extended storage, add a carrier protein of 0.1% human serum albumin or bovine serum albumin and freeze in working aliquots at -20 °C.