(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]propanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]hexanamido]hexanamido]-4-carbamoylbutanamido]-3-methylbutanamido]-4-carboxybutanamido]hexanamido]propanamido]-4-methylpentanamido]pentanedioic acid

• ChemBase ID: 155135
• Molecular Formular: C99H175N33O33
• Molecular Mass: 2355.6501
• Monoisotopic Mass: 2354.30300523
• SMILES: C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCC(=O)O)CC(C)C)C)CCCCN)CCC(=O)O)C(C)C)CCC(=O)N)CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)N)CCCNC(=N)N)CCCNC(=N)N)CC(=O)O)CC(C)C)CC(=O)O)C)CO)CCCNC(=N)N)CCC(=O)O)C
• InChI: InChI=1S/C99H175N33O33/c1-47(2)41-54(103)80(148)118-58(24-18-38-111-97(105)106)85(153)121-60(26-20-40-113-99(109)110)87(155)129-68(45-75(143)144)93(161)128-66(43-49(5)6)92(160)130-67(44-74(141)142)90(158)116-53(11)79(147)131-69(46-133)94(162)122-59(25-19-39-112-98(107)108)86(154)124-62(28-32-71(135)136)82(150)115-51(9)77(145)117-56(22-13-16-36-101)83(151)120-57(23-14-17-37-102)84(152)123-61(27-31-70(104)134)89(157)132-76(50(7)8)95(163)125-63(29-33-72(137)138)88(156)119-55(21-12-15-35-100)81(149)114-52(10)78(146)127-65(42-48(3)4)91(159)126-64(96(164)165)30-34-73(139)140/h47-69,76,133H,12-46,100-103H2,1-11H3,(H2,104,134)(H,114,149)(H,115,150)(H,116,158)(H,117,145)(H,118,148)(H,119,156)(H,120,151)(H,121,153)(H,122,162)(H,123,152)(H,124,154)(H,125,163)(H,126,159)(H,127,146)(H,128,161)(H,129,155)(H,130,160)(H,131,147)(H,132,157)(H,135,136)(H,137,138)(H,139,140)(H,141,142)(H,143,144)(H,164,165)(H4,105,106,111)(H4,107,108,112)(H4,109,110,113)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,76-/m0/s1
• InChIKey: LDXUYMBPAYIMJR-UGXKBFFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]propanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]hexanamido]hexanamido]-4-carbamoylbutanamido]-3-methylbutanamido]-4-carboxybutanamido]hexanamido]propanamido]-4-methylpentanamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]propanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]hexanamido]hexanamido]-4-carbamoylbutanamido]-3-methylbutanamido]-4-carboxybutanamido]hexanamido]propanamido]-4-methylpentanamido]pentanedioic acid
• Synonyms: Leu-Arg-Arg-Asp-Leu-Asp-Ala-Ser-Arg-Glu-Ala-Lys-Lys-Gln-Val-Glu-Lys-Ala-Leu-Glu

Database IDs

• CAS Number: 152044-86-5
• MDL Number: MFCD00792854
• PubChem SID: 162249273
• PubChem CID: 71312084

CALCULATED PROPERTIES

• Acid pKa: 2.8633087
• H Acceptors: 46
• H Donor: 40
• LogD (pH = 5.5): -21.526814
• LogD (pH = 7.4): -24.955494
• Log P: -19.222445
• Molar Refractivity: 609.9766 cm^3
• Polarizability: 227.21312 Å^3
• Polar Surface Area: 1129.8 Å^2
• Rotatable Bonds: 87
• 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)
• Compostion: Peptide content, ~65%
• Empirical Formula (Hill Notation): C99H175N33O33

DETAILS

Sigma Aldrich - L7783

Application
Of possible use as an antigen to produce a rheumatic fever vaccine.
Other Notes
Peptide from the conserved region of Group A streptococcal M protein.