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Also known as: 33017-11-7, Proinsulin c-peptide (human), Human c-peptide, Insulin c-peptide, Nmij-crm 6901a, Proinsulin c-peptide human

Molecular Formula

C₁₂₉H₂₁₁N₃₅O₄₈

Molecular Weight

3020.3 g/mol

InChI Key

VOUAQYXWVJDEQY-QENPJCQMSA-N

FDA UNII

O2J76Y002M

The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.

1 2D Structure

C-Peptide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S)-4-amino-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[2-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[2-[[2-[(2S)-2-[[2-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(1S)-4-amino-1-carboxy-4-oxobutyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

2.1.2 InChI

InChI=1S/C129H211N35O48/c1-58(2)42-77(155-113(195)74(31-39-102(184)185)151-127(209)105(65(15)16)162-114(196)71(25-32-88(131)167)145-95(174)54-141-126(208)104(64(13)14)161-115(197)72(26-33-89(132)168)150-118(200)80(45-61(7)8)156-121(203)83(48-103(186)187)159-112(194)73(30-38-101(182)183)148-107(189)67(18)143-109(191)69(130)24-36-99(178)179)111(193)138-50-93(172)135-49-92(171)136-55-98(177)163-40-20-22-86(163)124(206)140-51-94(173)142-66(17)106(188)137-52-96(175)146-84(56-165)122(204)157-81(46-62(9)10)119(201)152-75(27-34-90(133)169)128(210)164-41-21-23-87(164)125(207)160-78(43-59(3)4)116(198)144-68(19)108(190)154-79(44-60(5)6)117(199)149-70(29-37-100(180)181)110(192)139-53-97(176)147-85(57-166)123(205)158-82(47-63(11)12)120(202)153-76(129(211)212)28-35-91(134)170/h58-87,104-105,165-166H,20-57,130H2,1-19H3,(H2,131,167)(H2,132,168)(H2,133,169)(H2,134,170)(H,135,172)(H,136,171)(H,137,188)(H,138,193)(H,139,192)(H,140,206)(H,141,208)(H,142,173)(H,143,191)(H,144,198)(H,145,174)(H,146,175)(H,147,176)(H,148,189)(H,149,199)(H,150,200)(H,151,209)(H,152,201)(H,153,202)(H,154,190)(H,155,195)(H,156,203)(H,157,204)(H,158,205)(H,159,194)(H,160,207)(H,161,197)(H,162,196)(H,178,179)(H,180,181)(H,182,183)(H,184,185)(H,186,187)(H,211,212)/t66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,104-,105-/m0/s1

2.1.3 InChI Key

VOUAQYXWVJDEQY-QENPJCQMSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NCC(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C1CCCN1C(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)CNC(=O)C(C)NC(=O)CNC(=O)C2CCCN2C(=O)CNC(=O)CNC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C(CCC(=O)O)N

2.1.5 Isomeric 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)O)NC(=O)CNC(=O)[C@@H]2CCCN2C(=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)N

2.2 Other Identifiers

2.2.1 UNII

O2J76Y002M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cbx129801

2. C Peptide

3. C Peptide, Proinsulin

4. C-peptide

5. C-peptide, Proinsulin

6. Connecting Peptide

7. Proinsulin C Peptide

8. Proinsulin C-peptide

2.3.2 Depositor-Supplied Synonyms

1. 33017-11-7

2. Proinsulin C-peptide (human)

3. Human C-peptide

4. Insulin C-peptide

5. Nmij-crm 6901a

6. Proinsulin C-peptide Human

7. C-peptide (human) Acetate Salt

8. C-peptide, Proinsulin

9. C-peptide(human)

10. C-peptide, Human

11. Cbx129801

12. Cbx 129801

13. Gtpl6145

14. Chembl4594409

15. Dtxsid00186651

16. Mfcd00076295

17. C-peptide Fragment 3-33 Human, >=85% (hplc)

18. 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

19. H-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-oh

20. H-glu-val-glu-asp-leu-gln-val-arg-asp-val-glu-leu-ala-gly-ala-pro-gly-glu-gly-gly-leu-gln-pro-leu-ala-leu-glu-gly-ala-leu-gln-oh

21. Proinsulin Connecting Peptide (human), 1-de-l-arginine-2-de-l-arginine-34-de-l-lysine-35-de-l-arginine-

2.4 Create Date

2007-07-04

3 Chemical and Physical Properties

Molecular Formula	C₁₂₉H₂₁₁N₃₅O₄₈
Molecular Weight	3020.3 g/mol
XLogP3	-12.6
Hydrogen Bond Donor Count	41
Hydrogen Bond Acceptor Count	49
Rotatable Bond Count	101
Exact Mass	3019.5179284 g/mol
Monoisotopic Mass	3018.5145736 g/mol
Topological Polar Surface Area	1320 Å²
Heavy Atom Count	212
Formal Charge	0
Complexity	7190
Isotope Atom Count	0
Defined Atom Stereocenter Count	24
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1