(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S,3S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanoyl]pyrrolidin-2-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-3-phenylpropanamido]-3-carboxypropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]propanamido]propanamido]pentanedioic acid

• ChemBase ID: 133814
• Molecular Formular: C92H150N28O29
• Molecular Mass: 2112.3456
• Monoisotopic Mass: 2111.11235092
• SMILES: CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: OC[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)C)C)C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)CC(C)C)CC(=O)O)CCCNC(=N)N)Cc1ccccc1)CC(=O)O)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C92H150N28O29/c1-13-47(10)71(118-84(143)62-28-21-35-120(62)87(146)70(46(8)9)117-81(140)59(40-67(129)130)113-78(137)56(36-43(2)3)110-74(133)51(93)38-65(125)126)88(147)119-34-20-27-61(119)83(142)103-41-63(122)106-52(24-17-31-100-90(94)95)75(134)111-57(37-50-22-15-14-16-23-50)79(138)112-58(39-66(127)128)80(139)108-53(25-18-32-101-91(96)97)76(135)107-54(26-19-33-102-92(98)99)77(136)115-69(45(6)7)86(145)114-60(42-121)82(141)116-68(44(4)5)85(144)105-48(11)72(131)104-49(12)73(132)109-55(89(148)149)29-30-64(123)124/h14-16,22-23,43-49,51-62,68-71,121H,13,17-21,24-42,93H2,1-12H3,(H,103,142)(H,104,131)(H,105,144)(H,106,122)(H,107,135)(H,108,139)(H,109,132)(H,110,133)(H,111,134)(H,112,138)(H,113,137)(H,114,145)(H,115,136)(H,116,141)(H,117,140)(H,118,143)(H,123,124)(H,125,126)(H,127,128)(H,129,130)(H,148,149)(H4,94,95,100)(H4,96,97,101)(H4,98,99,102)/t47-,48-,49-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,68-,69-,70-,71-/m0/s1
• InChIKey: CNNRZOUCQVLOST-RBHZDPOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S,3S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanoyl]pyrrolidin-2-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-3-phenylpropanamido]-3-carboxypropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]propanamido]propanamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S,3S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanoyl]pyrrolidin-2-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-3-phenylpropanamido]-3-carboxypropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]propanamido]propanamido]pentanedioic acid
• Synonyms: Calcineurin substrate

Database IDs

• CAS Number: 113873-67-9
• MDL Number: MFCD00236901
• PubChem SID: 162228091
• PubChem CID: 16198110

CALCULATED PROPERTIES

• Acid pKa: 2.859654
• H Acceptors: 39
• H Donor: 32
• LogD (pH = 5.5): -17.009874
• LogD (pH = 7.4): -20.474566
• Log P: -14.795502
• Molar Refractivity: 552.3285 cm^3
• Polarizability: 203.72958 Å^3
• Polar Surface Area: 924.67 Å^2
• Rotatable Bonds: 66
• 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 - C5207

Amino Acid Sequence
Asp-Leu-Asp-Val-Pro-Ile-Pro-Gly-Arg-Phe-Asp-Arg-Arg-Val-Ser-Val-Ala-Ala-Glu
Biochem/physiol Actions
Peptide from the regulatory RII subunit of cAMP-dependent protein kinase. Useful in assays for protein phosphatase-2B (calcineurin) activity.