(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]pentanamido]-4-carboxybutanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]hexanoic acid

• ChemBase ID: 153626
• Molecular Formular: C79H141N31O20
• Molecular Mass: 1845.16054
• Monoisotopic Mass: 1844.09691607
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)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)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCCN)CCCNC(=N)N)Cc1ccc(cc1)O)CO)CCCNC(=N)N)CCCNC(=N)N)CO)CC(C)C)[C@H](CC)C)CCC(=O)O)CCCNC(=N)N)CCCNC(=N)N)N
• InChI: InChI=1S/C79H141N31O20/c1-5-43(4)60(109-66(121)51(28-29-59(114)115)102-63(118)48(19-11-33-94-76(85)86)99-62(117)47(18-10-32-93-75(83)84)98-61(116)46(82)16-6-8-30-80)72(127)106-54(38-42(2)3)67(122)107-56(40-111)69(124)101-49(20-12-34-95-77(87)88)64(119)103-52(22-14-36-97-79(91)92)73(128)110-37-15-23-58(110)71(126)108-57(41-112)70(125)105-55(39-44-24-26-45(113)27-25-44)68(123)100-50(21-13-35-96-78(89)90)65(120)104-53(74(129)130)17-7-9-31-81/h24-27,42-43,46-58,60,111-113H,5-23,28-41,80-82H2,1-4H3,(H,98,116)(H,99,117)(H,100,123)(H,101,124)(H,102,118)(H,103,119)(H,104,120)(H,105,125)(H,106,127)(H,107,122)(H,108,126)(H,109,121)(H,114,115)(H,129,130)(H4,83,84,93)(H4,85,86,94)(H4,87,88,95)(H4,89,90,96)(H4,91,92,97)/t43-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,60-/m0/s1
• InChIKey: KCZQVMUDQWHYKI-ZPXCENDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]pentanamido]-4-carboxybutanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]hexanoic acid
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]pentanamido]-4-carboxybutanamido]-3-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]hexanoic acid
• Synonyms: Crebtide

Database IDs

• MDL Number: MFCD03453644
• PubChem SID: 162247765
• PubChem CID: 16136337

CALCULATED PROPERTIES

• Acid pKa: 3.3257
• H Acceptors: 38
• H Donor: 35
• LogD (pH = 5.5): -24.173437
• LogD (pH = 7.4): -23.726637
• Log P: -14.364157
• Molar Refractivity: 522.5539 cm^3
• Polarizability: 182.83379 Å^3
• Polar Surface Area: 892.36 Å^2
• Rotatable Bonds: 65
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Compostion: Peptide content, ~80%
• Empirical Formula (Hill Notation): C79H141N31O20

DETAILS

Sigma Aldrich - C6110

Amino Acid Sequence
Lys-Arg-Arg-Glu-Ile-Leu-Ser-Arg-Arg-Pro-Ser-Tyr-Arg-Lys
Other Notes
Peptide corresponding to the consensus phosphorylation site at Ser133 of the cyclic AMP response element binding protein (CREB).