(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]-4-methylpentanamido]acetamido}acetamido)propanamido]hexanamido]-4-carbamoylbutanamido]propanamido]acetamido}-3-carboxypropanamido]-3-methylbutanoic acid

• ChemBase ID: 153530
• Molecular Formular: C50H80N18O16
• Molecular Mass: 1189.2812
• Monoisotopic Mass: 1188.59996857
• SMILES: C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)CNC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1c[nH]cn1)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)O)C(C)C)CC(=O)O)C)CCC(=O)N)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1nc[nH]c1)N)Cc1nc[nH]c1)CC(C)C)C
• InChI: InChI=1S/C50H80N18O16/c1-24(2)13-33(67-48(81)34(15-29-18-55-23-60-29)66-44(77)30(52)14-28-17-54-22-59-28)45(78)58-19-37(70)56-20-38(71)61-27(6)43(76)64-31(9-7-8-12-51)47(80)65-32(10-11-36(53)69)46(79)62-26(5)42(75)57-21-39(72)63-35(16-40(73)74)49(82)68-41(25(3)4)50(83)84/h17-18,22-27,30-35,41H,7-16,19-21,51-52H2,1-6H3,(H2,53,69)(H,54,59)(H,55,60)(H,56,70)(H,57,75)(H,58,78)(H,61,71)(H,62,79)(H,63,72)(H,64,76)(H,65,80)(H,66,77)(H,67,81)(H,68,82)(H,73,74)(H,83,84)/t26-,27-,30-,31-,32-,33-,34-,35-,41-/m0/s1
• InChIKey: STSKWZSBFZRSGP-GYDGUXFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]-4-methylpentanamido]acetamido}acetamido)propanamido]hexanamido]-4-carbamoylbutanamido]propanamido]acetamido}-3-carboxypropanamido]-3-methylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]-4-methylpentanamido]acetamido}acetamido)propanamido]hexanamido]-4-carbamoylbutanamido]propanamido]acetamido}-3-carboxypropanamido]-3-methylbutanoic acid
• Synonyms: Fibrinogen-γ Fragment 400-411; Fibrinogen-binding Inhibitor Peptide

Database IDs

• CAS Number: 89105-94-2
• MDL Number: MFCD00167528
• PubChem SID: 162247669
• PubChem CID: 9941719

CALCULATED PROPERTIES

• Acid pKa: 3.0947478
• H Acceptors: 20
• H Donor: 18
• LogD (pH = 5.5): -14.724697
• LogD (pH = 7.4): -13.668108
• Log P: -13.643529
• Molar Refractivity: 289.9084 cm^3
• Polarizability: 113.77235 Å^3
• Polar Surface Area: 547.19 Å^2
• Rotatable Bonds: 39
• 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

Pharmacology Properties

• Gene Information: human ... FGG(2266)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%
• Empirical Formula (Hill Notation): C50H80N18O16

DETAILS

Sigma Aldrich - F9145

Amino Acid Sequence
His-His-Leu-Gly-Gly-Ala-Lys-Gln-Ala-Gly-Asp-Val
Biochem/physiol Actions
Fibrinogen γ 400-411, a non-RGD containing sequence, is derived from plasmin digestion. If platelet activation is blocked with prostaglandin E1 blockade, it is required for the establishment of initial contact and support spreading but not firm adhesion on immobilized substrate. However, in activated platelets, single γ 400-411 sequence is no longer required for initiation of adhesion but becomes sufficient for firm adhesion. In contrast to the binding of whole fibrinogen, binding of fragment 400-411 does not lead to tyrosine phosphorylation for platelet proteins.