(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-carbamoylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]propanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid

• ChemBase ID: 155199
• Molecular Formular: C47H74N16O10
• Molecular Mass: 1023.19166
• Monoisotopic Mass: 1022.57738265
• SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N)CCC(=O)N)CCCNC(=N)N)C)CCCNC(=N)N)C
• InChI: InChI=1S/C47H74N16O10/c1-4-25(2)37(45(72)73)61-41(68)32(14-8-20-55-47(52)53)58-38(65)26(3)57-40(67)31(13-7-19-54-46(50)51)59-42(69)34-15-9-21-62(34)44(71)35-16-10-22-63(35)43(70)33(17-18-36(49)64)60-39(66)29(48)23-27-24-56-30-12-6-5-11-28(27)30/h5-6,11-12,24-26,29,31-35,37,56H,4,7-10,13-23,48H2,1-3H3,(H2,49,64)(H,57,67)(H,58,65)(H,59,69)(H,60,66)(H,61,68)(H,72,73)(H4,50,51,54)(H4,52,53,55)/t25-,26-,29-,31-,32-,33-,34-,35-,37-/m0/s1
• InChIKey: OVXIMRGEBNSORH-PJRZOMOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-carbamoylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]propanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-carbamoylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]propanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid
• Synonyms: Fibronectin Adhesion-promoting Peptide

Database IDs

• CAS Number: 125720-21-0
• MDL Number: MFCD00237001
• PubChem SID: 162249337
• PubChem CID: 9811927

CALCULATED PROPERTIES

• Acid pKa: 3.6564956
• H Acceptors: 17
• H Donor: 15
• LogD (pH = 5.5): -9.854778
• LogD (pH = 7.4): -8.184194
• Log P: -5.7813544
• Molar Refractivity: 285.7236 cm^3
• Polarizability: 103.80611 Å^3
• Polar Surface Area: 432.12 Å^2
• Rotatable Bonds: 28
• 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: ≥95% (HPLC)
• Compostion: Peptide content, ~70%
• Empirical Formula (Hill Notation): C47H74N16O10

DETAILS

Sigma Aldrich - F3667

Amino Acid Sequence
Trp-Gln-Pro-Pro-Arg-Ala-Arg-Ile
Other Notes
Sequence found in the carboxy-terminal heparin-binding domain of fibronectin.