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Hepcidin-25 peptide

CAT: 0466-SB001-01MGSize: 0.1 mgDry Ice: NoHazardous: No
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Description
Hepcidin, also known as LEAP-1 (liver-expressed antimicrobial peptide) or Hepcidin-25 is a hormone of 25 amino acids. Hepcidin is a cationic, cysteine-rich and tightly folded peptide stabilized by 4 disulfide bonds that plays a major role in innate immunity and iron homeostasis. Hepcidin inhibits iron transport by binding to the iron export channel ferroportin which is located on the basolateral surface of gut enterocytes and the plasma membrane of reticuloendothelial cells (macrophages) . Hepcidin breaks down the transporter protein in the lysosome. Inhibiting ferroportin prevents iron exportation and iron is retained in cells. Hepcidin is regulated by iron through a complex of integral hemochromatosis proteins, like HFE, HJV and transferrin receptor 2. Hepcidin is also characterized by is antimicrobial activity in several vertebrate species, exerting its antimicrobial effect against both Gram-positive and Gram-negative bacteria as well as yeast, with for example an IC50 value against Saccharomyces cerevisae of 18 µM.
CAS Number
342809-17-0
Product Name Alternative
LEAP-1
Sequence
DTHFPICIFCCGCCHRSKCGMCCKT-OH
Peptide Number
SB001
Disulfide Bonds
Cys7 – Cys23, Cys10 – Cys13, Cys11 – Cys19, Cys14 – Cys22

Chemical Information

Hepcidin 25 (human)

See also: Hepcidin (preferred).

CAS Number342809-17-0
PubChem CID133065673
IUPAC Name(3S)-3-amino-4-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S,3S)-1-[[(1R,6R,12R,17R,20S,23S,26R,31R,34R,39R,42S,45S,48S,51S,59S)-51-(4-aminobutyl)-31-[[(2S)-6-amino-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1-oxohexan-2-yl]carbamoyl]-20-benzyl-23-[(2S)-butan-2-yl]-45-(3-carbamimidamidopropyl)-48-(hydroxymethyl)-42-(1H-imidazol-5-ylmethyl)-59-(2-methylsulfanylethyl)-7,10,19,22,25,33,40,43,46,49,52,54,57,60,63,64-hexadecaoxo-3,4,14,15,28,29,36,37-octathia-8,11,18,21,24,32,41,44,47,50,53,55,58,61,62,65-hexadecazatetracyclo[32.19.8.26,17.212,39]pentahexacontan-26-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-oxobutanoic acid
Molecular FormulaC113H170N34O31S9
Molecular Weight2789.4
XLogP-10.9
Topological Polar Surface Area1250
Hydrogen Bond Donor Count36
Hydrogen Bond Acceptor Count46
Rotatable Bond Count49
Heavy Atom Count187
Formal Charge0
Complexity5940
SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H]4CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]5CCCN5C(=O)[C@H](CC6=CC=CC=C6)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(=O)O)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CSSC[C@@H](C(=O)NCC(=O)N3)NC2=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC4=O)CC8=CN=CN8)CCCNC(=N)N)CO)CCCCN)CCSC)CC9=CC=CC=C9
InChI
InChI=1S/C113H170N34O31S9/c1-8-56(3)86-108(173)132-69(36-60-22-12-10-13-23-60)97(162)139-80-52-183-182-48-76-101(166)140-78-50-185-186-51-79(138-95(160)68(30-35-179-7)126-83(151)43-122-91(156)74(46-180-181-47-75(137-104(80)169)92(157)123-44-84(152)127-76)136-94(159)65(26-16-18-31-114)129-100(165)73(45-148)135-93(158)67(28-20-33-121-113(117)118)128-98(163)70(131-103(78)168)38-62-41-119-54-124-62)105(170)141-77(102(167)130-66(27-17-19-32-115)96(161)146-89(59(6)150)112(177)178)49-184-187-53-81(106(171)143-86)142-109(174)87(57(4)9-2)144-107(172)82-29-21-34-147(82)111(176)72(37-61-24-14-11-15-25-61)134-99(164)71(39-63-42-120-55-125-63)133-110(175)88(58(5)149)145-90(155)64(116)40-85(153)154/h10-15,22-25,41-42,54-59,64-82,86-89,148-150H,8-9,16-21,26-40,43-53,114-116H2,1-7H3,(H,119,124)(H,120,125)(H,122,156)(H,123,157)(H,126,151)(H,127,152)(H,128,163)(H,129,165)(H,130,167)(H,131,168)(H,132,173)(H,133,175)(H,134,164)(H,135,158)(H,136,159)(H,137,169)(H,138,160)(H,139,162)(H,140,166)(H,141,170)(H,142,174)(H,143,171)(H,144,172)(H,145,155)(H,146,161)(H,153,154)(H,177,178)(H4,117,118,121)/t56-,57-,58+,59+,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,86-,87-,88-,89-/m0/s1
InChIKey
XJOTXKZIRSHZQV-RXHOOSIZSA-N
Chemical Structure
2D Structure
2D structure of Hepcidin 25 (human)
CAS: 342809-17-0
CID: 133065673
Formula: C113H170N34O31S9
MW: 2789.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight2789.4
XLogP3-10.9
Hydrogen Bond Donor Count36
Hydrogen Bond Acceptor Count46
Rotatable Bond Count49
Exact Mass2788.0291202
Monoisotopic Mass2787.0257653
Topological Polar Surface Area1250 Ų
Heavy Atom Count187
Formal Charge0
Complexity5940
Isotope Atom Count0
Defined Atom Stereocenter Count27
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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