1-[2-(2-{2-[2-(2-aminoacetamido)-5-carbamimidamidopentanamido]acetamido}-3-carboxypropanamido)-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 103861
• Molecular Formular: C23H39N9O10
• Molecular Mass: 601.61006
• Monoisotopic Mass: 601.28198849
• SMILES: CC(O)C(NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)CN)C(=O)N1CCCC1C(=O)O
• Canonical SMILES: NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)O)C(O)C)CC(=O)O)CCCNC(=N)N
• InChI: InChI=1S/C23H39N9O10/c1-11(33)18(21(40)32-7-3-5-14(32)22(41)42)31-20(39)13(8-17(36)37)30-16(35)10-28-19(38)12(29-15(34)9-24)4-2-6-27-23(25)26/h11-14,18,33H,2-10,24H2,1H3,(H,28,38)(H,29,34)(H,30,35)(H,31,39)(H,36,37)(H,41,42)(H4,25,26,27)
• InChIKey: UMZVBZDHGKJFGQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(2-{2-[2-(2-aminoacetamido)-5-carbamimidamidopentanamido]acetamido}-3-carboxypropanamido)-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: 1-[2-(2-{2-[2-(2-aminoacetamido)-5-carbamimidamidopentanamido]acetamido}-3-carboxypropanamido)-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: Gly-Arg-Gly-Asp-Thr-Pro; GRGDTP; GLY-ARG-GLY-ASP-THR-PRO

Database IDs

• CAS Number: 108682-58-2
• MDL Number: MFCD00076465
• PubChem SID: 162092467; 24895222
• PubChem CID: 4644096

CALCULATED PROPERTIES

• Rotatable Bonds: 17
• Lipinski's Rule of Five: false
• Acid pKa: 3.1175885
• H Acceptors: 14
• H Donor: 11
• LogD (pH = 5.5): -10.217592
• LogD (pH = 7.4): -10.344159
• Log P: -10.217766
• Molar Refractivity: 151.1093 cm^3
• Polarizability: 55.077145 Å^3
• Polar Surface Area: 319.46 Å^2

PROPERTIES

Safety Information

• Storage Condition: -20°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 ... COL1A1(1277), COL1A2(1278), FN1(2335), VTN(7448)mouse ... COL1A1(12842), COL1A2(12843), FN1(14268), VTN(22370)rat ... COL1A1(29393), COL1A2(84352), FN1(25661), VTN(29169)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02153108

Inhibits the cell attachment of fibronectin, vitronectin and collagen Type I.

Sigma Aldrich - G5646

Amino Acid Sequence
Gly-Arg-Gly-Asp-Thr-Pro
Biochem/physiol Actions
Inhibits cell attachment of fibronectin, vitronectin, and Type I collagen.

REFERENCES

• Dedhar, S., et al., J. Cell. Biol., 104: 585, (1987).
• Gehisen, K.R., et al., J. Cell. Biol., 106: 925, 1988).