(4S)-4-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carboxyethyl]carbamoyl}methyl)carbamoyl]-4-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]butanoic acid

• ChemBase ID: 132982
• Molecular Formular: C70H112N24O23
• Molecular Mass: 1657.78528
• Monoisotopic Mass: 1656.83321596
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccc(cc1)O)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CCCNC(=N)N)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)C)CCC(=O)O)CC(=O)O)Cc1nc[nH]c1)C)CO
• InChI: InChI=1S/C70H112N24O23/c1-33(2)53(92-62(110)47(28-52(101)102)85-50(98)30-80-59(107)43(20-21-51(99)100)87-55(103)34(3)82-58(106)41(72)26-38-16-18-40(97)19-17-38)65(113)90-46(27-39-29-77-32-81-39)61(109)83-36(5)57(105)93-54(37(6)96)66(114)91-48(31-95)63(111)88-44(12-7-8-22-71)67(115)94-25-11-15-49(94)64(112)84-35(4)56(104)86-42(13-9-23-78-69(73)74)60(108)89-45(68(116)117)14-10-24-79-70(75)76/h16-19,29,32-37,41-49,53-54,95-97H,7-15,20-28,30-31,71-72H2,1-6H3,(H,77,81)(H,80,107)(H,82,106)(H,83,109)(H,84,112)(H,85,98)(H,86,104)(H,87,103)(H,88,111)(H,89,108)(H,90,113)(H,91,114)(H,92,110)(H,93,105)(H,99,100)(H,101,102)(H,116,117)(H4,73,74,78)(H4,75,76,79)/t34-,35-,36-,37+,41-,42-,43-,44-,45-,46-,47-,48-,49-,53-,54-/m0/s1
• InChIKey: JJNXAJMLWIIHBK-QOECIXTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carboxyethyl]carbamoyl}methyl)carbamoyl]-4-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carboxyethyl]carbamoyl}methyl)carbamoyl]-4-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]butanoic acid
• Synonyms: Tyr-Ala-Glu-Gly-Asp-Val-His-Ala-Thr-Ser-Lys-Pro-Ala-Arg-Arg; Peptide Sequencing Standard

Database IDs

• MDL Number: MFCD00214050
• PubChem SID: 162227259
• PubChem CID: 71308615

CALCULATED PROPERTIES

• Acid pKa: 3.0924344
• H Acceptors: 32
• H Donor: 28
• LogD (pH = 5.5): -19.72173
• LogD (pH = 7.4): -17.303562
• Log P: -16.803595
• Molar Refractivity: 426.9434 cm^3
• Polarizability: 158.5555 Å^3
• Polar Surface Area: 775.72 Å^2
• Rotatable Bonds: 52
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• 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: 2-8°C

Product Information

• Packaging: vial of ~20 nmol
• Mol. Weight: average mol wt 1,658 Da by calculation; monoisotopic mol wt 1,657 Da

DETAILS

Sigma Aldrich - P2046

Application
Useful in evaluating the efficiency of protein sequencers.