(4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-3-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-4-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 155626
• Molecular Formular: C68H115N23O20
• Molecular Mass: 1574.7828
• Monoisotopic Mass: 1573.8688732
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)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)O)CCCNC(=N)N)CC(C)C)CCCNC(=N)N)CC(=O)O)Cc1ccccc1)CCC(=O)O)CO)C)CO)[C@H](CC)C)NC(=O)[C@H](CCCNC(=N)N)N
• InChI: InChI=1S/C68H115N23O20/c1-6-36(4)52(90-56(101)40(19-10-11-25-69)81-54(99)39(70)18-12-26-77-66(71)72)63(108)89-47(33-92)60(105)80-37(5)53(98)88-48(34-93)61(106)82-41(23-24-50(94)95)55(100)85-45(31-38-16-8-7-9-17-38)58(103)86-46(32-51(96)97)59(104)83-42(20-13-27-78-67(73)74)64(109)91-29-15-22-49(91)62(107)87-44(30-35(2)3)57(102)84-43(65(110)111)21-14-28-79-68(75)76/h7-9,16-17,35-37,39-49,52,92-93H,6,10-15,18-34,69-70H2,1-5H3,(H,80,105)(H,81,99)(H,82,106)(H,83,104)(H,84,102)(H,85,100)(H,86,103)(H,87,107)(H,88,98)(H,89,108)(H,90,101)(H,94,95)(H,96,97)(H,110,111)(H4,71,72,77)(H4,73,74,78)(H4,75,76,79)/t36-,37-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,52-/m0/s1
• InChIKey: NPUSRFWRIUYFIF-KTFPRAGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-3-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-4-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-3-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-4-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: BPDEtide

Database IDs

• MDL Number: MFCD00214605
• PubChem SID: 162249764
• PubChem CID: 71312176

CALCULATED PROPERTIES

• Acid pKa: 3.0492263
• H Acceptors: 31
• H Donor: 27
• LogD (pH = 5.5): -18.624512
• LogD (pH = 7.4): -16.510736
• Log P: -13.570689
• Molar Refractivity: 425.1472 cm^3
• Polarizability: 153.76329 Å^3
• Polar Surface Area: 730.51 Å^2
• Rotatable Bonds: 53
• 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 ... PRKG1(5592)

Product Information

• Purity: ≥90% (HPLC)
• Mol. Weight: calculated mol wt 1575

DETAILS

Sigma Aldrich - B7681

Amino Acid Sequence
Arg-Lys-Ile-Ser-Ala-Ser-Glu-Phe-Asp-Arg-Pro-Leu-Arg
Biochem/physiol Actions
Substrate for PKG.
General description
Specific substrate for protein kinase G (PKG) with no phosphorylation detected for calcium/calmodulin kinase II (CaMKII) or protein kinase C (PKC).