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[Pyr1]apelin-13 (human)

CAT: 0466-SB311-1MGSize: 1 mgDry Ice: NoHazardous: No
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Description
[Pyr1]apelin-13 (human) (CAS: 217082-60-5) Apelin GPCR-Receptor The Apelin receptor, also known as APJ, APLNR, and AGTRL1, is a member of the class A family of G protein-coupled receptors (GPCRs) . It has been identified in various species, including mouse, rat, cow, rhesus macaque, Xenopus laevis, and Danio rerio, and it shares structural similarities with the angiotensin II type l receptor (AT1) . However, despite a 54% homology in transmembrane regions with AT1, it does not bind angiotensin II. Initially designated as an "orphan" GPCR, due to the absence of a known ligand, O'Dowd & al. named it APJ in 19935. Comprising 380 amino acid residues, APJ features the characteristic 7-transmembrane domain structure, typical of a class A GPCR. Nowadays, it is known that APLNR depicts physiological roles, including regulation of cardiovascular function, fluid homeostasis, the adipoinsular axis, gastrointestinal and immunomodulatory functions. Apelin isoforms Apelin (APLN) endogenous APJ ligand, is a 36-amino acids peptide, initially discovered in bovine stomach extracts. It is expressed and released by cultured adipocytes from a 77-amino acids prepropeptide, whose sequence was identified in human and bovine tissues, with the last 23 residues of the C terminus being identical in mammals. Cleavage of this preproapelin at specific sites generates different isoforms, including apelin-36, apelin-17, apelin-13, and [Pyr1]apelin-13, which all act as agonists at the apelin receptor and equipotent mediators of vascular tone and cardiac contractility in human tissues in vitro. All of these predicted isoforms have been shown to be present in vivo, but the predominant isoforms in plasma are [Pyr1]apelin-13, apelin-13 and apelin-17, with [Pyr1]apelin-13 and apelin-13. Among these, [Pyr1]apelin-13 and apelin-13 are notably robust activators of apelin receptors in cell lines, while apelin-36 demonstrates remarkable efficacy as an inhibitor of HIV infection in vitro. [Pyr1]apelin-13 peptide Although apelin-36 is the most widely expressed APLN isoform, apelin-13 remains the more potent and abundant peptide in blood circulation. Notably, [Pyr1]apelin-13 (CAS: 217082-60-5) is the predominant isoform in human cardiac tissue, showcasing its physiological significance in regulating cardiovascular function. SB-PEPTIDE is pleased to offer [Pyr1]apelin-13, as well as apelin-36 (see apelin-36 webpage), for further research into their multifaceted functions and therapeutic applications.
CAS Number
217082-60-5
Product Name Alternative
[Pyr1]apelin-13 (human)
Sequence
XRPRLSHKGPMPF (X=pyrGlu)
Peptide Number
SB311

Chemical Information

[Pyr1]apelin-13

P-Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe is a thirteen-membered polypeptide consisting of p-Glu, Arg, Pro, Arg, Leu, Ser, His, Lys, Gly, Pro, Met, Pro and Phe residues joined in sequence. It has a role as a neuroprotective agent, an apoptosis inhibitor and a human metabolite. It is a tautomer of a [Pyr1]apelin-13(2+).

CAS Number217082-60-5
PubChem CID25085173
IUPAC Name(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-1-[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-1-[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
Molecular FormulaC69H108N22O16S
Molecular Weight1533.8
XLogP-5.9
Topological Polar Surface Area618
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count21
Rotatable Bond Count44
Heavy Atom Count108
Formal Charge0
Complexity3160
SMILES
CC(C)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N2CCC[C@H]2C(=O)N[C@@H](CCSC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H]5CCCN5C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H]6CCC(=O)N6
InChI
InChI=1S/C69H108N22O16S/c1-39(2)32-47(85-57(96)43(17-9-26-76-68(71)72)82-63(102)52-20-12-29-90(52)65(104)45(18-10-27-77-69(73)74)83-58(97)44-22-23-54(93)80-44)59(98)88-50(37-92)61(100)86-48(34-41-35-75-38-79-41)60(99)81-42(16-7-8-25-70)56(95)78-36-55(94)89-28-11-19-51(89)62(101)84-46(24-31-108-3)66(105)91-30-13-21-53(91)64(103)87-49(67(106)107)33-40-14-5-4-6-15-40/h4-6,14-15,35,38-39,42-53,92H,7-13,16-34,36-37,70H2,1-3H3,(H,75,79)(H,78,95)(H,80,93)(H,81,99)(H,82,102)(H,83,97)(H,84,101)(H,85,96)(H,86,100)(H,87,103)(H,88,98)(H,106,107)(H4,71,72,76)(H4,73,74,77)/t42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
InChIKey
GGMAXEWLXWJGSF-PEWBXTNBSA-N
Chemical Structure
2D Structure
2D structure of [Pyr1]apelin-13
CAS: 217082-60-5
CID: 25085173
Formula: C69H108N22O16S
MW: 1533.8
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight1533.8
XLogP3-5.9
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count21
Rotatable Bond Count44
Exact Mass1532.80343662
Monoisotopic Mass1532.80343662
Topological Polar Surface Area618 Ų
Heavy Atom Count108
Formal Charge0
Complexity3160
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes