(4S)-4-{[(1S)-1-[({[({2-[(2S)-2-[({[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]-3-carboxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-carbamoyl-1-oxobutan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}methyl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-4-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-methylbutanamido]acetamido}-4-carbamoylbutanamido]-3-methylbutanamido]butanoic acid

• ChemBase ID: 130981
• Molecular Formular: C153H259N49O52
• Molecular Mass: 3616.99066
• Monoisotopic Mass: 3614.91286977
• SMILES: C[C@@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)CNC(=O)CNC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)N)CCCNC(=N)N)CCC(=O)O)C)CCC(=O)O)CC(=O)O)CC(C)C)CCC(=O)N)CCC(=O)N)CCC(=O)O)CC(C)C)C)CO)CC(C)C)CCC(=O)N)CC(C)C)C)CC(C)C)CCC(=O)O)CO)CC(C)C)CCC(=O)N
• InChI: InChI=1S/C153H259N49O52/c1-71(2)55-94(193-134(237)91(40-48-119(222)223)189-148(251)122(78(15)16)200-135(238)86(33-41-105(156)205)179-112(212)67-175-147(250)121(77(13)14)199-136(239)88(35-43-107(158)207)188-139(242)97(58-74(7)8)194-142(245)100(61-120(224)225)197-133(236)90(39-47-118(220)221)182-124(227)80(18)177-129(232)89(38-46-117(218)219)186-130(233)84(29-23-51-167-152(162)163)183-126(229)82(155)27-22-50-166-151(160)161)128(231)172-63-110(210)169-62-109(209)170-68-115(215)201-53-25-31-103(201)145(248)174-64-111(211)176-79(17)123(226)171-65-113(213)180-101(69-203)144(247)196-99(60-76(11)12)141(244)190-92(36-44-108(159)208)149(252)202-54-26-32-104(202)146(249)198-95(56-72(3)4)137(240)178-81(19)125(228)192-96(57-73(5)6)138(241)185-85(37-45-116(216)217)127(230)173-66-114(214)181-102(70-204)143(246)195-98(59-75(9)10)140(243)187-87(34-42-106(157)206)132(235)184-83(28-20-21-49-154)131(234)191-93(150(253)254)30-24-52-168-153(164)165/h71-104,121-122,203-204H,20-70,154-155H2,1-19H3,(H2,156,205)(H2,157,206)(H2,158,207)(H2,159,208)(H,169,210)(H,170,209)(H,171,226)(H,172,231)(H,173,230)(H,174,248)(H,175,250)(H,176,211)(H,177,232)(H,178,240)(H,179,212)(H,180,213)(H,181,214)(H,182,227)(H,183,229)(H,184,235)(H,185,241)(H,186,233)(H,187,243)(H,188,242)(H,189,251)(H,190,244)(H,191,234)(H,192,228)(H,193,237)(H,194,245)(H,195,246)(H,196,247)(H,197,236)(H,198,249)(H,199,239)(H,200,238)(H,216,217)(H,218,219)(H,220,221)(H,222,223)(H,224,225)(H,253,254)(H4,160,161,166)(H4,162,163,167)(H4,164,165,168)/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,121-,122-/m0/s1
• InChIKey: JEPNOJXFZHBCTB-ZCUALFGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-[({[({2-[(2S)-2-[({[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]-3-carboxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-carbamoyl-1-oxobutan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}methyl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-4-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-methylbutanamido]acetamido}-4-carbamoylbutanamido]-3-methylbutanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-[({[({2-[(2S)-2-[({[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]-3-carboxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-carbamoyl-1-oxobutan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}methyl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)methyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-4-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-methylbutanamido]acetamido}-4-carbamoylbutanamido]-3-methylbutanamido]butanoic acid
• Synonyms: Arg-Arg-Glu-Ala-Glu-Asp-Leu-Gln-Val-Gly-Gln-Val-Glu-Leu-Gly-Gly-Gly-Pro-Gly-Ala-Gly-Ser-Leu-Gln-Pro-Leu-Ala-Leu-Glu-Gly-Ser-Leu-Gln-Lys-Arg; Insulin C chain; C-Peptide human; Proinsulin connecting peptide; Proinsulin C-Peptide (55-89) human

Database IDs

• CAS Number: 11097-48-6
• MDL Number: MFCD00076294
• PubChem SID: 162225259
• PubChem CID: 71308369

CALCULATED PROPERTIES

• Acid pKa: 2.8132796
• H Acceptors: 63
• H Donor: 55
• LogD (pH = 5.5): -32.460236
• LogD (pH = 7.4): -35.845196
• Log P: -30.076523
• Molar Refractivity: 912.887 cm^3
• Polarizability: 345.36166 Å^3
• Polar Surface Area: 1646.18 Å^2
• Rotatable Bonds: 125
• Lipinski's Rule of Five: false

PROPERTIES

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 ... INS(3630)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C153H259N49O52

DETAILS

Sigma Aldrich - C5051

Biochem/physiol Actions
In proinsulin the insulin A and B chains are linked by C peptide. During the biosynthesis of insulin, the C peptide promotes proper protein folding and disulfide bond placement after which it is cleaved. The cleaved peptide may inhibit insulin aggregation and is stored and released from the β cells with insulin in a one-to-one molar ratio. C peptide is a marker for β cell function in vivo; levels are enhanced in insulin resistance or insuloma and reduced in insulin insufficiency (type I diabetes). C peptide may alleviate the vascular damage and neuropathy associated with insulin depletion.

Sigma Aldrich - C4999

Amino Acid Sequence
Arg-Arg-Glu-Ala-Glu-Asp-Leu-Gln-Val-Gly-Gln-Val-Glu-Leu-Gly-Gly-Gly-Pro-Gly-Ala-Gly-Ser-Leu-Gln-Pro-Leu-Ala-Leu-Glu-Gly-Ser-Leu-Gln-Lys-Arg
Other Notes
Human proinsulin, the single-chain peptide precursor of insulin, consists of the insulin A and B chains connected by the 31 amino acid C-peptide. Cleavage of proinsulin by proteolytic enzymes produces insulin and free C-peptide. The product here is the 35-mer peptide (Arg-Arg-C-Peptide-Lys-Arg) observed to separate the insulin A and B chains.1
Biochem/physiol Actions
C-Peptide Fragment (55-89) is a fragment derived from the proinsulin C-peptide. C-peptide has cell signaling activity that involves calcium-dependent intracellular signaling. C-Peptide Fragment 55-89 may be used to help researchers understand the role of specific sequences within the C-peptide in binding, conformation and function of C-peptide.
C-Peptide was initially thought to have no intrinsic biological activity. More recent research has identified multiple biological effects of C-peptide, including binding to cell membranes, activation of signaling pathways, and stimulation of Na+,K+-ATPase and endothelial nitric oxide synthetase. However, the exact function of C-peptide is unclear due to conflicting physiological effects.