(3S)-3-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S,2R)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-carboxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxypropyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}propanoic acid; trifluoroacetic acid

• ChemBase ID: 155655
• Molecular Formular: C96H150F3N33O32
• Molecular Mass: 2335.4153096
• Monoisotopic Mass: 2334.10767447
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(=O)O)C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=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)CC(=O)O)Cc1nc[nH]c1)[C@H](CC)C)C)CC(=O)N)CCCNC(=N)N)CCCNC(=N)N)[C@H](O)C)CCCNC(=N)N)CO)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H]([C@H](O)C)N)Cc1ccc(cc1)O)C)CC(=O)O)Cc1ccccc1)C
• InChI: InChI=1S/C94H149N33O30.C2HF3O2/c1-11-42(3)70(125-86(152)59(31-50-19-14-13-15-20-50)119-85(151)62(36-68(138)139)118-75(141)44(5)111-82(148)58(32-51-24-26-53(132)27-25-51)121-91(157)73(49(10)131)127-87(153)69(96)47(8)129)89(155)113-45(6)76(142)123-63(40-128)78(144)108-38-65(134)115-55(22-17-29-106-93(100)101)81(147)126-72(48(9)130)88(154)109-39-66(135)114-54(21-16-28-105-92(98)99)79(145)116-56(23-18-30-107-94(102)103)80(146)120-61(34-64(95)133)83(149)112-46(7)77(143)124-71(43(4)12-2)90(156)122-60(33-52-37-104-41-110-52)84(150)117-57(74(97)140)35-67(136)137;3-2(4,5)1(6)7/h13-15,19-20,24-27,37,41-49,54-63,69-73,128-132H,11-12,16-18,21-23,28-36,38-40,96H2,1-10H3,(H2,95,133)(H2,97,140)(H,104,110)(H,108,144)(H,109,154)(H,111,148)(H,112,149)(H,113,155)(H,114,135)(H,115,134)(H,116,145)(H,117,150)(H,118,141)(H,119,151)(H,120,146)(H,121,157)(H,122,156)(H,123,142)(H,124,143)(H,125,152)(H,126,147)(H,127,153)(H,136,137)(H,138,139)(H4,98,99,105)(H4,100,101,106)(H4,102,103,107);(H,6,7)/t42-,43-,44-,45-,46-,47+,48+,49+,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,69-,70-,71-,72-,73-;/m0./s1
• InChIKey: CJBPFVMGYBOAOJ-AYVQDJQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S,2R)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-carboxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxypropyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}propanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S,2R)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-carboxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxypropyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}propanoic acid; trifluoroacetic acid
• Synonyms: Protein kinase A inhibitor fragment 5-24 amide trifluoroacetate salt

Database IDs

• MDL Number: MFCD03788008
• PubChem SID: 162249793
• PubChem CID: 71312191

CALCULATED PROPERTIES

• Acid pKa: 3.139873
• H Acceptors: 41
• H Donor: 39
• LogD (pH = 5.5): -24.445747
• LogD (pH = 7.4): -22.050962
• Log P: -21.188446
• Molar Refractivity: 577.0274 cm^3
• Polarizability: 212.94148 Å^3
• Polar Surface Area: 1055.23 Å^2
• Rotatable Bonds: 72
• 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 ... PKIA(5569)

Product Information

• Purity: ≥95% (HPLC)
• Compostion: Peptide content, ~75%
• Shipped in: wet ice
• Mol. Weight: calculated mol wt 2219

DETAILS

Sigma Aldrich - P7739

Amino Acid Sequence
Thr-Thr-Tyr-Ala-Asp-Phe-Ile-Ala-Ser-Gly-Arg-Thr-Gly-Arg-Arg-Asn-Ala-Ile-His-Asp-NH2
Biochem/physiol Actions
Binds to the catalytic subunit of protein kinase A (PKA), mimicking the protein substrate