(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]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-3-methylbutanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid

• ChemBase ID: 155614
• Molecular Formular: C65H113N21O20
• Molecular Mass: 1508.72142
• Monoisotopic Mass: 1507.84707512
• 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](Cc1c[nH]cn1)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)Cc1nc[nH]c1)CC(C)C)C)NC(=O)[C@H](CCCCN)N
• InChI: InChI=1S/C65H113N21O20/c1-31(2)25-43(81-52(93)34(7)75-55(96)39(16-11-13-23-67)77-54(95)38(68)15-10-12-22-66)60(101)82-44(27-37-29-72-30-74-37)61(102)78-40(17-14-24-73-65(70)71)56(97)79-41(18-20-47(69)88)57(98)80-42(19-21-48(89)90)58(99)86-51(36(9)87)63(104)85-50(33(5)6)62(103)83-45(28-49(91)92)59(100)76-35(8)53(94)84-46(64(105)106)26-32(3)4/h29-36,38-46,50-51,87H,10-28,66-68H2,1-9H3,(H2,69,88)(H,72,74)(H,75,96)(H,76,100)(H,77,95)(H,78,102)(H,79,97)(H,80,98)(H,81,93)(H,82,101)(H,83,103)(H,84,94)(H,85,104)(H,86,99)(H,89,90)(H,91,92)(H,105,106)(H4,70,71,73)/t34-,35-,36+,38-,39-,40-,41-,42-,43-,44-,45-,46-,50-,51-/m0/s1
• InChIKey: SKKYWKZBFLZUDN-CFWYEEEESA-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]-3-(1H-imidazol-4-yl)propanamido]-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]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-4-carboxybutanamido]-3-hydroxybutanamido]-3-methylbutanamido]-3-carboxypropanamido]propanamido]-4-methylpentanoic acid
• Synonyms: Autocamtide 3

Database IDs

• MDL Number: MFCD00467166
• PubChem SID: 162249752
• PubChem CID: 71312172

CALCULATED PROPERTIES

• Acid pKa: 3.1368377
• H Acceptors: 27
• H Donor: 24
• LogD (pH = 5.5): -17.463034
• LogD (pH = 7.4): -15.036026
• Log P: -14.283025
• Molar Refractivity: 384.856 cm^3
• Polarizability: 147.4071 Å^3
• Polar Surface Area: 693.06 Å^2
• Rotatable Bonds: 53
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble

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)mouse ... CAMK2A(12322), CAMK2B(12323), CAMK2D(108058), CAMK2G(12325)rat ... CAMK2A(25400), CAMK2B(24245), CAMK2D(24246), CAMK2G(171140)

Product Information

• Purity: ≥95% (HPLC)
• Compostion: Peptide content, ≥80%
• Mol. Weight: calculated mol wt 1507

DETAILS

Sigma Aldrich - A8473

Amino Acid Sequence
Lys-Lys-Ala-Leu-His-Arg-Gln-Glu-Thr-Val-Asp-Ala-Leu
Biochem/physiol Actions
Selective calcium/calmodulin-dependent protein kinase II (CaMKII) substrate.