(2S)-2-[(2S)-2-{2-[(2S,3S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]acetamido}-3-hydroxypropanamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 133001
• Molecular Formular: C26H42N8O8
• Molecular Mass: 594.66048
• Monoisotopic Mass: 594.31256034
• SMILES: CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)NC(=O)CNC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H](Cc1ccc(cc1)O)N
• InChI: InChI=1S/C26H42N8O8/c1-3-14(2)21(34-22(38)17(27)11-15-6-8-16(36)9-7-15)24(40)31-12-20(37)32-19(13-35)23(39)33-18(25(41)42)5-4-10-30-26(28)29/h6-9,14,17-19,21,35-36H,3-5,10-13,27H2,1-2H3,(H,31,40)(H,32,37)(H,33,39)(H,34,38)(H,41,42)(H4,28,29,30)/t14-,17-,18-,19-,21-/m0/s1
• InChIKey: MWOGMBZGFFZBMK-LJZWMIMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{2-[(2S,3S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]acetamido}-3-hydroxypropanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{2-[(2S,3S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]acetamido}-3-hydroxypropanamido]-5-carbamimidamidopentanoic acid
• Synonyms: Laminin Fragment 929-933; Tyr-Ile-Gly-Ser-Arg

Database IDs

• CAS Number: 110590-64-2
• MDL Number: MFCD00076472
• PubChem SID: 162227278; 24900419
• PubChem CID: 123977

CALCULATED PROPERTIES

• Acid pKa: 3.3797379
• H Acceptors: 12
• H Donor: 11
• LogD (pH = 5.5): -6.386466
• LogD (pH = 7.4): -4.713095
• Log P: -4.3523207
• Molar Refractivity: 160.359 cm^3
• Polarizability: 58.465748 Å^3
• Polar Surface Area: 282.08 Å^2
• Rotatable Bonds: 18
• 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 - T7154

Amino Acid Sequence
Tyr-Ile-Gly-Ser-Arg
Biochem/physiol Actions
Tyr-Ile-Gly-Ser-Arg is a fragment of domain III of the laminin B1 chain . It is a major receptor binding site in laminin. It competes with laminin for the cell surface receptor. It is an inhibitor of tumor growth and metastasis.