(3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-pyrrolidin-2-ylformamido]propanoic acid

• ChemBase ID: 131877
• Molecular Formular: C59H86N16O14
• Molecular Mass: 1243.41294
• Monoisotopic Mass: 1242.65094151
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]1CCCN1
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1)CC(=O)O)CC(=O)O)Cc1nc[nH]c1)Cc1ccccc1)C
• InChI: InChI=1S/C59H86N16O14/c1-31(2)23-40(52(83)67-38(20-14-22-65-59(61)62)51(82)68-39(49(60)80)24-34-15-9-7-10-16-34)69-53(84)41(25-35-17-11-8-12-18-35)72-57(88)47(32(3)4)74-55(86)42(26-36-29-63-30-66-36)70-54(85)43(27-45(76)77)73-58(89)48(33(5)6)75-56(87)44(28-46(78)79)71-50(81)37-19-13-21-64-37/h7-12,15-18,29-33,37-44,47-48,64H,13-14,19-28H2,1-6H3,(H2,60,80)(H,63,66)(H,67,83)(H,68,82)(H,69,84)(H,70,85)(H,71,81)(H,72,88)(H,73,89)(H,74,86)(H,75,87)(H,76,77)(H,78,79)(H4,61,62,65)/t37-,38-,39-,40-,41-,42-,43-,44-,47-,48-/m0/s1
• InChIKey: MXQCHKYVLFWFJG-SYQAEKSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-pyrrolidin-2-ylformamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-pyrrolidin-2-ylformamido]propanoic acid
• Synonyms: Pro-Asp-Val-Asp-His-Val-Phe-Leu-Arg-Phe-NH2

Database IDs

• CAS Number: 121801-61-4
• MDL Number: MFCD00133779
• PubChem SID: 162226154
• PubChem CID: 11972244

CALCULATED PROPERTIES

• Acid pKa: 3.3536296
• H Acceptors: 19
• H Donor: 17
• LogD (pH = 5.5): -6.9275913
• LogD (pH = 7.4): -6.1867304
• Log P: -6.1588326
• Molar Refractivity: 328.9585 cm^3
• Polarizability: 124.57586 Å^3
• Polar Surface Area: 482.2 Å^2
• Rotatable Bonds: 37
• 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 - P2178

Biochem/physiol Actions
Cardioinhibitory; inhibits contraction of the oviduct visceral muscle, but potentiates contraction of the extensortibiae muscle
Other Notes
FMRF-amide-like neuropeptide originally isolated from locust (Schistocera gregaria)