(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-3-methylbutanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid

• ChemBase ID: 155202
• Molecular Formular: C65H118N22O20
• Molecular Mass: 1527.76782
• Monoisotopic Mass: 1526.88927429
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)N)O
• 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)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)C)CC(=O)O)C(C)C)[C@H](O)C)CCC(=O)O)CCC(=O)N)CCCNC(=N)N)CCCNC(=N)N)CC(C)C)C)NC(=O)[C@H](CCCCN)N
• InChI: InChI=1S/C65H118N22O20/c1-31(2)28-43(83-51(94)34(7)76-54(97)38(17-11-13-25-67)78-53(96)37(68)16-10-12-24-66)60(103)80-40(19-15-27-75-65(72)73)55(98)79-39(18-14-26-74-64(70)71)56(99)81-41(20-22-46(69)89)57(100)82-42(21-23-47(90)91)58(101)87-50(36(9)88)62(105)86-49(33(5)6)61(104)84-44(30-48(92)93)59(102)77-35(8)52(95)85-45(63(106)107)29-32(3)4/h31-45,49-50,88H,10-30,66-68H2,1-9H3,(H2,69,89)(H,76,97)(H,77,102)(H,78,96)(H,79,98)(H,80,103)(H,81,99)(H,82,100)(H,83,94)(H,84,104)(H,85,95)(H,86,105)(H,87,101)(H,90,91)(H,92,93)(H,106,107)(H4,70,71,74)(H4,72,73,75)/t34-,35-,36+,37-,38-,39-,40-,41-,42-,43-,44-,45-,49-,50-/m0/s1
• InChIKey: WRSMVHZKPDCKNQ-DBSTUJSUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-3-methylbutanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-3-methylbutanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid
• Synonyms: Autocamtide 2 trifluoroacetate salt

Database IDs

• CAS Number: 129198-88-5
• MDL Number: MFCD00143639
• PubChem SID: 162249340
• PubChem CID: 71312099

CALCULATED PROPERTIES

• Acid pKa: 3.1370153
• H Acceptors: 29
• H Donor: 26
• LogD (pH = 5.5): -19.565172
• LogD (pH = 7.4): -17.243275
• Log P: -14.373569
• Molar Refractivity: 401.2858 cm^3
• Polarizability: 149.53644 Å^3
• Polar Surface Area: 726.28 Å^2
• Rotatable Bonds: 55
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL
• Apperance: white powder

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 ... CAMK1(8536)mouse ... CAMK1(52163)rat ... CAMK1(171503)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ≥60%
• Empirical Formula (Hill Notation): C65H118N22O20

DETAILS

Sigma Aldrich - A0591

Amino Acid Sequence
Lys-Lys-Ala-Leu-Arg-Arg-Gln-Glu-Thr-Val-Asp-Ala-Leu
Substrates
A highly selective synthetic Ca2+/calmodulin-dependent protein kinase substrate.1 The peptide contains the sequence around the autophosphorylation site in the autoinhibitory domain of calmodulin-dependent protein kinase II (CaM kinase II).