(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]propanamido]-3-(phosphonooxy)propanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]propanoic acid

• ChemBase ID: 153802
• Molecular Formular: C31H58N13O12P
• Molecular Mass: 835.845881
• Monoisotopic Mass: 835.40655099
• SMILES: C[C@@H](C(=O)N[C@@H](COP(=O)(O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)N
• Canonical SMILES: NC(=N)NCCC[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)C)C(C)C)COP(=O)(O)O)C)NC(=O)[C@H](CCCNC(=N)N)N
• InChI: InChI=1S/C31H58N13O12P/c1-15(2)22(27(49)40-17(4)29(51)52)43-26(48)21-10-7-13-44(21)28(50)20(14-56-57(53,54)55)42-23(45)16(3)39-25(47)19(9-6-12-38-31(35)36)41-24(46)18(32)8-5-11-37-30(33)34/h15-22H,5-14,32H2,1-4H3,(H,39,47)(H,40,49)(H,41,46)(H,42,45)(H,43,48)(H,51,52)(H4,33,34,37)(H4,35,36,38)(H2,53,54,55)/t16-,17-,18-,19-,20-,21-,22-/m0/s1
• InChIKey: SYLMVFSDXGIMAW-CPDXTSBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]propanamido]-3-(phosphonooxy)propanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]propanamido]-3-(phosphonooxy)propanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]propanoic acid
• Synonyms: Arg-Arg-Ala-pSer-Pro-Val-Ala

Database IDs

• MDL Number: MFCD02094090
• PubChem SID: 162247941
• PubChem CID: 71311735

CALCULATED PROPERTIES

• Acid pKa: 1.3641709
• H Acceptors: 18
• H Donor: 15
• LogD (pH = 5.5): -11.632986
• LogD (pH = 7.4): -10.984054
• Log P: -10.945946
• Molar Refractivity: 220.2346 cm^3
• Polarizability: 77.83497 Å^3
• Polar Surface Area: 419.69 Å^2
• Rotatable Bonds: 24
• 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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C31H58N13O12P

DETAILS

Sigma Aldrich - A4602

Amino Acid Sequence
Arg-Arg-Ala-pSer-Pro-Val-Ala
Biochem/physiol Actions
The phosphoseryl peptide RRApSPVA can provide a sensitive evaluation of the majority of acid and alkaline phosphatases, while being refractory to protein phosphatases.