(2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-[(2S)-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-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide

• ChemBase ID: 130459
• Molecular Formular: C43H66N12O12S2
• Molecular Mass: 1007.18734
• Monoisotopic Mass: 1006.43645761
• SMILES: O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]1N(C(=O)[C@@H]2NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](N)CSSC2)Cc2ccc(O)cc2)[C@@H](C)CC)CCC(=O)N)CC(=O)N)CCC1)CC(C)C
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@@H](Cc2ccc(cc2)O)NC(=O)[C@@H](N)CSSC[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CC(C)C)C
• InChI: InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
• InChIKey: XNOPRXBHLZRZKH-DSZYJQQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-[(2S)-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-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide
• IUPAC Traditional name: oxytocin
• Brand Name: Pitocin
• Synonyms: Oxytocin; α-Hypophamine; Oxytocic hormone; Oxytocin

Database IDs

• CAS Number: 50-56-6
• EC Number: 200-048-4
• MDL Number: MFCD00076731
• Beilstein Number: 3586108
• PubChem SID: 24897975; 24897994; 162224738
• PubChem CID: 439302
• CHEBI ID: 7872
• ATC CODE: H01BB02
• CHEMBL: 265640
• Chemspider ID: 388434
• DrugBank ID: DB00107
• IUPHAR ligand ID: 2176
• KEGG ID: D00089
• Unique Ingredient Identifier: 1JQS135EYN
• Wikipedia Title: Oxytocin

CALCULATED PROPERTIES

• Acid pKa: 9.503691
• H Acceptors: 13
• H Donor: 12
• LogD (pH = 5.5): -6.967106
• LogD (pH = 7.4): -5.3115015
• Log P: -4.997379
• Molar Refractivity: 252.1114 cm^3
• Polarizability: 98.93987 Å^3
• Polar Surface Area: 399.53 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• RTECS: RS7534000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Admin Routes: Intranasal, IV, IM
• Bioavailability: nil
• Excretion: Biliary and renal
• Half Life: 1–6 min
• Metabolism: hepatic oxytocinases
• Protein Bound: 30%
• Legal Status: Rx-only (US)
• Pregnancy Category: A (Australia)
• Gene Information: human ... OXT(5020); human ... OXT(5020), OXTR(5021)rat ... Oxtr(25342)

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C43H66N12O12S2

DETAILS

Sigma Aldrich - O4375

Amino Acid Sequence
Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Stimulates uterine contraction and lactation; increases Na+ excretion; stimulates myometrial GTPase and phospholipase C.
Physical form
Lyophilized powder containing 3% oxytocin with mannitol and buffer salts.

Sigma Aldrich - 75968

Amino Acid Sequence
Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Stimulates uterine contraction and lactation; increases Na+ excretion; stimulates myometrial GTPase and phospholipase C.