1-(2-{2-[2-(2-{2-[(1-{1-[2-(2-{2-[2-(2-{2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{2-[2-(2-amino-3-methylpentanamido)-3-hydroxybutanamido]-3-hydroxypropanamido}-3-phenylpropanamido)-4-carboxybutanamido]-4-carboxybutanamido}propanamido)hexanamido]acetamido}-4-methylpentanamido)-3-carboxypropanamido]-5-carbamimidamidopentanamido}-3-methylpentanamido)-3-carbamoylpropanamido]-4-carboxybutanamido}-5-carbamimidamidopentanamido)-4-(methylsulfanyl)butanoyl]pyrrolidine-2-carbonyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanamido}-5-carbamimidamidopentanamido)-3-carboxypropanamido]propanamido}-4-(methylsulfanyl)butanoyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 155286
• Molecular Formular: C124H205N39O39S2
• Molecular Mass: 2930.3224
• Monoisotopic Mass: 2928.46982994
• SMILES: CCC(C)C(C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC(Cc1ccccc1)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(C)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)CC)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCSC)C(=O)N1CCCC1C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)NC(CCSC)C(=O)N1CCCC1C(=O)O)N
• Canonical SMILES: NCCCCC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)O)CCSC)C)CC(=O)O)CCCNC(=N)N)CCCNC(=N)N)CCSC)CCCNC(=N)N)CCC(=O)O)CC(=O)N)C(CC)C)CCCNC(=N)N)CC(=O)O)CC(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(C(CC)C)N)CO)Cc1ccccc1)CCC(=O)O)CCC(=O)O)C
• InChI: InChI=1S/C124H205N39O39S2/c1-12-62(5)94(127)114(195)160-96(66(9)165)116(197)158-83(60-164)112(193)154-79(55-67-26-15-14-16-27-67)109(190)149-75(38-41-91(172)173)105(186)148-73(36-39-89(168)169)100(181)141-64(7)97(178)144-68(28-17-18-44-125)99(180)140-59-88(167)143-78(54-61(3)4)108(189)156-82(58-93(176)177)111(192)147-72(32-22-48-139-124(134)135)106(187)159-95(63(6)13-2)115(196)157-80(56-87(126)166)110(191)150-74(37-40-90(170)171)104(185)146-69(29-19-45-136-121(128)129)102(183)153-77(43-53-204-11)117(198)162-50-24-34-85(162)119(200)161-49-23-33-84(161)113(194)151-71(31-21-47-138-123(132)133)101(182)145-70(30-20-46-137-122(130)131)103(184)155-81(57-92(174)175)107(188)142-65(8)98(179)152-76(42-52-203-10)118(199)163-51-25-35-86(163)120(201)202/h14-16,26-27,61-66,68-86,94-96,164-165H,12-13,17-25,28-60,125,127H2,1-11H3,(H2,126,166)(H,140,180)(H,141,181)(H,142,188)(H,143,167)(H,144,178)(H,145,182)(H,146,185)(H,147,192)(H,148,186)(H,149,190)(H,150,191)(H,151,194)(H,152,179)(H,153,183)(H,154,193)(H,155,184)(H,156,189)(H,157,196)(H,158,197)(H,159,187)(H,160,195)(H,168,169)(H,170,171)(H,172,173)(H,174,175)(H,176,177)(H,201,202)(H4,128,129,136)(H4,130,131,137)(H4,132,133,138)(H4,134,135,139)
• InChIKey: JRQDGUSHUYLSHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{2-[2-(2-{2-[(1-{1-[2-(2-{2-[2-(2-{2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{2-[2-(2-amino-3-methylpentanamido)-3-hydroxybutanamido]-3-hydroxypropanamido}-3-phenylpropanamido)-4-carboxybutanamido]-4-carboxybutanamido}propanamido)hexanamido]acetamido}-4-methylpentanamido)-3-carboxypropanamido]-5-carbamimidamidopentanamido}-3-methylpentanamido)-3-carbamoylpropanamido]-4-carboxybutanamido}-5-carbamimidamidopentanamido)-4-(methylsulfanyl)butanoyl]pyrrolidine-2-carbonyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanamido}-5-carbamimidamidopentanamido)-3-carboxypropanamido]propanamido}-4-(methylsulfanyl)butanoyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: 1-(2-{2-[2-(2-{2-[(1-{1-[2-(2-{2-[2-(2-{2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{2-[2-(2-amino-3-methylpentanamido)-3-hydroxybutanamido]-3-hydroxypropanamido}-3-phenylpropanamido)-4-carboxybutanamido]-4-carboxybutanamido}propanamido)hexanamido]acetamido}-4-methylpentanamido)-3-carboxypropanamido]-5-carbamimidamidopentanamido}-3-methylpentanamido)-3-carbamoylpropanamido]-4-carboxybutanamido}-5-carbamimidamidopentanamido)-4-(methylsulfanyl)butanoyl]pyrrolidine-2-carbonyl}pyrrolidin-2-yl)formamido]-5-carbamimidamidopentanamido}-5-carbamimidamidopentanamido)-3-carboxypropanamido]propanamido}-4-(methylsulfanyl)butanoyl)pyrrolidine-2-carboxylic acid
• Synonyms: Ile-Thr-Ser-Phe-Glu-Glu-Ala-Lys-Gly-Leu-Asp-Arg-Ile-Asn-Glu-Arg-Met-Pro-Pro-Arg-Arg-Asp-Ala-Met-Pro; Calcineurin autoinhibitory fragment

Database IDs

• CAS Number: 148067-21-4
• MDL Number: MFCD00214597
• PubChem SID: 162249424; 24892659
• PubChem CID: 16219117

CALCULATED PROPERTIES

• Acid pKa: 2.9437292
• H Acceptors: 53
• H Donor: 44
• LogD (pH = 5.5): -22.166275
• LogD (pH = 7.4): -22.150414
• Log P: -22.150425
• Molar Refractivity: 764.6927 cm^3
• Polarizability: 282.55347 Å^3
• Polar Surface Area: 1279.02 Å^2
• Rotatable Bonds: 97
• 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: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C124H205N39O39S2

DETAILS

Sigma Aldrich - C3937

Application
Membrane-impermeable blocker of calcineurin.1