(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]hexanamido]-3-phenylpropanamido]-3-carbamoylpropanamido]propanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-methylpentanamido]hexanamido]acetamido}propanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-4-(methylsulfanyl)butanamido]-4-methylpentanamido]propanoic acid

• ChemBase ID: 155244
• Molecular Formular: C103H185N31O24S
• Molecular Mass: 2273.8293
• Monoisotopic Mass: 2272.39294696
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)N
• Canonical SMILES: NCCCC[C@@H](C(=O)NCC(=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)C)CC(C)C)CCSC)[C@H](O)C)[C@H](O)C)CC(C)C)[C@H](CC)C)C)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)CCCCN)CCCCN)Cc1ccccc1)CC(=O)N)C)CCCNC(=N)N)CCCNC(=N)N)CCCCN)CC(C)C
• InChI: InChI=1S/C103H185N31O24S/c1-17-58(10)80(98(154)131-75(50-57(8)9)97(153)133-82(63(15)136)100(156)134-81(62(14)135)99(155)126-72(39-46-159-16)92(148)127-73(48-55(4)5)93(149)119-61(13)101(157)158)132-84(140)59(11)117-79(138)53-116-86(142)66(33-21-25-40-104)122-95(151)74(49-56(6)7)128-90(146)68(35-23-27-42-106)124-89(145)71(38-30-45-115-103(112)113)125-88(144)70(37-29-44-114-102(110)111)120-83(139)60(12)118-94(150)77(52-78(109)137)130-96(152)76(51-64-31-19-18-20-32-64)129-91(147)69(36-24-28-43-107)123-87(143)67(34-22-26-41-105)121-85(141)65(108)47-54(2)3/h18-20,31-32,54-63,65-77,80-82,135-136H,17,21-30,33-53,104-108H2,1-16H3,(H2,109,137)(H,116,142)(H,117,138)(H,118,150)(H,119,149)(H,120,139)(H,121,141)(H,122,151)(H,123,143)(H,124,145)(H,125,144)(H,126,155)(H,127,148)(H,128,146)(H,129,147)(H,130,152)(H,131,154)(H,132,140)(H,133,153)(H,134,156)(H,157,158)(H4,110,111,114)(H4,112,113,115)/t58-,59-,60-,61-,62+,63+,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,80-,81-,82-/m0/s1
• InChIKey: LRKHMNPQPYICFK-RBGVSSEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]hexanamido]-3-phenylpropanamido]-3-carbamoylpropanamido]propanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-methylpentanamido]hexanamido]acetamido}propanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-4-(methylsulfanyl)butanamido]-4-methylpentanamido]propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]hexanamido]-3-phenylpropanamido]-3-carbamoylpropanamido]propanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-methylpentanamido]hexanamido]acetamido}propanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-4-(methylsulfanyl)butanamido]-4-methylpentanamido]propanoic acid
• Synonyms: CaM kinase II (290-309); Calmodulin-dependent Protein Kinase II fragment 290-309

Database IDs

• CAS Number: 115044-69-4
• MDL Number: MFCD00076719
• PubChem SID: 162249382
• PubChem CID: 71312108

CALCULATED PROPERTIES

• Acid pKa: 3.534465
• H Acceptors: 35
• H Donor: 34
• LogD (pH = 5.5): -26.390303
• LogD (pH = 7.4): -23.01629
• Log P: -9.712636
• Molar Refractivity: 610.5357 cm^3
• Polarizability: 232.07755 Å^3
• Polar Surface Area: 927.65 Å^2
• Rotatable Bonds: 82
• 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

Pharmacology Properties

• Gene Information: human ... CAMK2A(815), CAMK2B(816), CAMK2D(817), CAMK2G(818)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ≥70%
• Empirical Formula (Hill Notation): C103H185N31O24S

DETAILS

Sigma Aldrich - C4926

Amino Acid Sequence
Leu-Lys-Lys-Phe-Asn-Ala-Arg-Arg-Lys-Leu-Lys-Gly-Ala-Ile-Leu-Thr-Thr-Met-Leu-Ala
Biochem/physiol Actions
Potent Ca2+/calmodulin-dependent protein kinase II inhibitor.