(2S)-5-amino-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-[(2S)-butan-2-yl]-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 155686
• Molecular Formular: C48H74N12O12S2
• Molecular Mass: 1075.30436
• Monoisotopic Mass: 1074.49905787
• SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CSSC2(CCCCC2)CC(=O)N[C@@H](C(=O)N1)Cc1ccc(cc1)OC)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
• Canonical SMILES: NCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC2(CCCCC2)CC(=O)N[C@H](Cc2ccc(cc2)OC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N1)CC(=O)N)CCC(=O)N)[C@H](CC)C
• InChI: InChI=1S/C48H74N12O12S2/c1-4-27(2)40-46(70)56-31(16-17-36(50)61)42(66)57-33(23-37(51)62)43(67)58-34(47(71)60-21-9-11-35(60)45(69)55-30(10-8-20-49)41(65)53-25-38(52)63)26-73-74-48(18-6-5-7-19-48)24-39(64)54-32(44(68)59-40)22-28-12-14-29(72-3)15-13-28/h12-15,27,30-35,40H,4-11,16-26,49H2,1-3H3,(H2,50,61)(H2,51,62)(H2,52,63)(H,53,65)(H,54,64)(H,55,69)(H,56,70)(H,57,66)(H,58,67)(H,59,68)/t27-,30-,31-,32-,33-,34-,35-,40-/m0/s1
• InChIKey: ZWVZXPFUQHTUKV-SZQHDTAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-amino-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-[(2S)-butan-2-yl]-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: (2S)-5-amino-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-[(2S)-butan-2-yl]-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide
• Synonyms: [β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin

Database IDs

• CAS Number: 77327-45-8
• MDL Number: MFCD00135712
• PubChem SID: 162249824
• PubChem CID: 71312201

CALCULATED PROPERTIES

• Acid pKa: 11.361693
• H Acceptors: 13
• H Donor: 11
• LogD (pH = 5.5): -6.8194375
• LogD (pH = 7.4): -5.96701
• Log P: -3.8218317
• Molar Refractivity: 273.3734 cm^3
• Polarizability: 107.43632 Å^3
• Polar Surface Area: 388.53 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... OXT(5020), OXTR(5021)rat ... OXT(18429), OXTR(18430)

Product Information

• Purity: ≥93% (HPLC)
• Empirical Formula (Hill Notation): C48H74N12O12S2

DETAILS

Sigma Aldrich - O6887

Amino Acid Sequence
β-Mercapto-β,β-Cyclopentamethylenepropionyl-MeTyr-Ile-Gln-Asn-Cys-Pro-Orn-Gly-NH2 [Disulfide Bridge: 1-6]
General description
Potent oxytocin antagonist.