19-amino-13-(butan-2-yl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxylic acid

• ChemBase ID: 134015
• Molecular Formular: C30H44N8O10S2
• Molecular Mass: 740.84796
• Monoisotopic Mass: 740.26218165
• SMILES: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)Cc1ccc(cc1)O)N)C(=O)O)CC(=O)N)CCC(=O)N
• Canonical SMILES: CCC(C1NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(N)CSSCC(NC(=O)C(NC(=O)C(NC1=O)CCC(=O)N)CC(=O)N)C(=O)O)C
• InChI: InChI=1S/C30H44N8O10S2/c1-3-14(2)24-29(46)34-18(8-9-22(32)40)26(43)36-20(11-23(33)41)27(44)37-21(30(47)48)13-50-49-12-17(31)25(42)35-19(28(45)38-24)10-15-4-6-16(39)7-5-15/h4-7,14,17-21,24,39H,3,8-13,31H2,1-2H3,(H2,32,40)(H2,33,41)(H,34,46)(H,35,42)(H,36,43)(H,37,44)(H,38,45)(H,47,48)
• InChIKey: ITRWUGOBSKHPTA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 19-amino-13-(butan-2-yl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxylic acid
• IUPAC Traditional name: 19-amino-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(sec-butyl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxylic acid
• Synonyms: [Ile3]-Pressinoic acid; Tocinoic acid

Database IDs

• CAS Number: 34330-23-9
• MDL Number: MFCD00076737
• PubChem SID: 24900110; 162228292
• PubChem CID: 4202286

CALCULATED PROPERTIES

• Acid pKa: 3.2019262
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -5.6652975
• LogD (pH = 7.4): -5.841515
• Log P: -5.6672177
• Molar Refractivity: 181.5282 cm^3
• Polarizability: 71.37248 Å^3
• Polar Surface Area: 315.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - T3149

Amino Acid Sequence
Cys-Tyr-Ile-Gln-Asn-Cys [Disulfide bridge: 1-6]
Biochem/physiol Actions
Oxytocin inhibitor; induces maternal behavior.
Other Notes
N-terminal hexapeptide fragment of oxytocin.