(2S)-2-[(2S)-2-[(2S)-2-[(2S,5S)-5-[(2S)-2-[(2R)-2-[(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-carboxybutanamido]-5-carbamimidamidopentanamido]-6-carbamimidamido-2-oxohexyl]-4-carbamoylbutanamido]-4-carboxybutanamido]-4-oxo-2-(propan-2-yl)hexanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid

• ChemBase ID: 155276
• Molecular Formular: C65H114N20O21
• Molecular Mass: 1511.72206
• Monoisotopic Mass: 1510.84674077
• SMILES: C[C@@H](C(=O)C[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)CC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)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)C[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)C[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)CCC(=O)O)CCC(=O)N)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)O)C)NC(=O)[C@H](CCCCN)N
• InChI: InChI=1S/C65H114N20O21/c1-32(2)28-46(63(105)106)85-54(96)36(7)78-62(104)45(31-52(93)94)84-56(98)38(33(3)4)30-47(86)34(5)76-59(101)43(19-22-50(89)90)81-55(97)37(18-21-49(69)88)29-48(87)40(16-12-26-74-64(70)71)79-60(102)42(17-13-27-75-65(72)73)83-61(103)44(20-23-51(91)92)80-53(95)35(6)77-58(100)41(15-9-11-25-67)82-57(99)39(68)14-8-10-24-66/h32-46H,8-31,66-68H2,1-7H3,(H2,69,88)(H,76,101)(H,77,100)(H,78,104)(H,79,102)(H,80,95)(H,81,97)(H,82,99)(H,83,103)(H,84,98)(H,85,96)(H,89,90)(H,91,92)(H,93,94)(H,105,106)(H4,70,71,74)(H4,72,73,75)/t34-,35-,36-,37+,38-,39-,40-,41-,42-,43-,44-,45-,46-/m0/s1
• InChIKey: COEHZSYVSXUBHI-CYZNULJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S,5S)-5-[(2S)-2-[(2R)-2-[(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-carboxybutanamido]-5-carbamimidamidopentanamido]-6-carbamimidamido-2-oxohexyl]-4-carbamoylbutanamido]-4-carboxybutanamido]-4-oxo-2-(propan-2-yl)hexanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S,5S)-5-[(2S)-2-[(2R)-2-[(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]propanamido]-4-carboxybutanamido]-5-carbamimidamidopentanamido]-6-carbamimidamido-2-oxohexyl]-4-carbamoylbutanamido]-4-carboxybutanamido]-2-isopropyl-4-oxohexanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid
• Synonyms: AIP; [Ala9]-Autocamtide 2; Autocamtide 2-related inhibitory peptide

Database IDs

• CAS Number: 167114-91-2
• PubChem SID: 162249414
• PubChem CID: 71312113

CALCULATED PROPERTIES

• Acid pKa: 3.0385745
• H Acceptors: 30
• H Donor: 24
• LogD (pH = 5.5): -15.068698
• LogD (pH = 7.4): -15.050109
• Log P: -15.0497055
• Molar Refractivity: 396.1141 cm^3
• Polarizability: 147.18306 Å^3
• Polar Surface Area: 719.29 Å^2
• Rotatable Bonds: 57
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: lyophilized 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 ... CAMK2A(815), CAMK2B(816), CAMK2D(817)mouse ... CAMK2A(12322), CAMK2B(12323), CAMK2D(108058)rat ... CAMK2A(25400), CAMK2B(24245), CAMK2D(24246)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ≥70%
• Empirical Formula (Hill Notation): C64H116N22O19

DETAILS

Sigma Aldrich - A4308

Amino Acid Sequence
Lys-Lys-Ala-Leu-Arg-Arg-Gln-Glu-Ala-Val-Asp-Ala-Leu
Biochem/physiol Actions
Potent inhibitor of calmodulin-depentent protein kinase II.