4-(2-{2-[2-(2-aminopropanamido)-3-carboxypropanamido]-3-hydroxypropanamido}acetamido)-4-({[(1-{[1-({1-[(1-{[1-({[({[({1-[(4-carbamimidamido-1-carboxybutyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)-3-carboxypropyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-carboxyethyl)carbamoyl]methyl}carbamoyl)butanoic acid

• ChemBase ID: 103256
• Molecular Formular: C63H97N19O26
• Molecular Mass: 1536.55598
• Monoisotopic Mass: 1535.68521432
• SMILES: CC(C)CC(NC(=O)C(Cc1ccccc1)NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C(CO)NC(=O)C(CC(=O)O)NC(=O)C(C)N)C(=O)NC(C)C(=O)NC(CCC(=O)O)C(=O)NCC(=O)NCC(=O)NCC(=O)NC(C(C)C)C(=O)NC(CCCNC(=N)N)C(=O)O
• Canonical SMILES: OCC(C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)O)CCCNC(=N)N)C(C)C)CCC(=O)O)C)CC(C)C)Cc1ccccc1)CC(=O)O)CCC(=O)O)NC(=O)C(NC(=O)C(N)C)CC(=O)O
• InChI: InChI=1S/C63H97N19O26/c1-29(2)19-37(57(102)73-32(6)53(98)76-35(15-17-48(91)92)55(100)70-24-43(85)68-23-42(84)69-25-46(88)82-51(30(3)4)61(106)77-36(62(107)108)13-10-18-67-63(65)66)79-58(103)38(20-33-11-8-7-9-12-33)80-59(104)39(21-49(93)94)75-45(87)27-71-54(99)34(14-16-47(89)90)74-44(86)26-72-56(101)41(28-83)81-60(105)40(22-50(95)96)78-52(97)31(5)64/h7-9,11-12,29-32,34-41,51,83H,10,13-28,64H2,1-6H3,(H,68,85)(H,69,84)(H,70,100)(H,71,99)(H,72,101)(H,73,102)(H,74,86)(H,75,87)(H,76,98)(H,77,106)(H,78,97)(H,79,103)(H,80,104)(H,81,105)(H,82,88)(H,89,90)(H,91,92)(H,93,94)(H,95,96)(H,107,108)(H4,65,66,67)
• InChIKey: JWICNZAGYSIBAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{2-[2-(2-aminopropanamido)-3-carboxypropanamido]-3-hydroxypropanamido}acetamido)-4-({[(1-{[1-({1-[(1-{[1-({[({[({1-[(4-carbamimidamido-1-carboxybutyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)-3-carboxypropyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-carboxyethyl)carbamoyl]methyl}carbamoyl)butanoic acid
• IUPAC Traditional name: 4-(2-{2-[2-(2-aminopropanamido)-3-carboxypropanamido]-3-hydroxypropanamido}acetamido)-4-({[(1-{[1-({1-[(1-{[1-({[({[({1-[(4-carbamimidamido-1-carboxybutyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)-3-carboxypropyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-carboxyethyl)carbamoyl]methyl}carbamoyl)butanoic acid
• Synonyms: Fibrinopeptide A human; Ala-Asp-Ser-Gly-Glu-Gly-Asp-Phe-Leu-Ala-Glu-Gly-Gly-Gly-Val-Arg; FIBRINOPEPTIDE A; Fibrinopeptide A 人类

Database IDs

• CAS Number: 25422-31-5
• MDL Number: MFCD00076437
• PubChem SID: 24894837; 162090351
• PubChem CID: 25081464

CALCULATED PROPERTIES

• Acid pKa: 2.8773515
• H Acceptors: 30
• H Donor: 25
• LogD (pH = 5.5): -20.27878
• LogD (pH = 7.4): -25.299337
• Log P: -16.056753
• Molar Refractivity: 373.3981 cm^3
• Polarizability: 142.25616 Å^3
• Polar Surface Area: 731.15 Å^2
• Rotatable Bonds: 51
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C
• 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 ... FGA(2243)

Product Information

• Purity: ≥96% (HPLC)

DETAILS

MP Biomedicals - 02151124

Source/Species: Human

Sigma Aldrich - F3254

Amino Acid Sequence
Ala-Asp-Ser-Gly-Glu-Gly-Asp-Phe-Leu-Ala-Glu-Gly-Gly-Gly-Val-Arg
Biochem/physiol Actions
Fibrin polymerization is initiated by thrombin cleavage of fibrinopeptide A from fibrinogen α chains, exposing two E domain E(A) sites. The phenylalanine at α chain residue 8 is important for efficient thrombin-catalyzed proteolysis of fibrinogen. Substitution of tyrosine for phenylalanine blocks sequential fibrinopeptide release and, thus, blocks polymerization and clot formation.

REFERENCES

• Johnson, B.J. and May, W.P., J. Pharm. Sci., 58: 1568 (1969).