H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2
PubChem CID
16129620
Structure
Molecular Formula
Synonyms
- SERMORELIN
- 86168-78-7
- Sermorelin (INN)
- CHEBI:9118
- D08509
Molecular Weight
3357.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2007-07-03
- Modify:2025-01-18
Description
Sermorelin is a 29 amino acid polypeptide that is used to treat growth problems (usually in children) due to growth hormone deficiency. It is the biologically active fragment of human growth hormone-releasing factor (GHRH). It has a role as a diagnostic agent. It is a polypeptide and a peptide hormone.
Sermorelin acetate is the acetate salt of an amidated synthetic 29-amino acid peptide (GRF 1-29 NH 2 ) that corresponds to the amino-terminal segment of the naturally occurring human growth hormone-releasing hormone (GHRH or GRF) consisting of 44 amino acid residues
The biologically active fragment of human growth hormone-releasing factor, consisting of GHRH(1-29)-amide. This N-terminal sequence is identical in several mammalian species, such as human, pig, and cattle. It is used to diagnose or treat patients with GROWTH HORMONE deficiency.
See also: Sermorelin (annotation moved to).
Chemical Structure Depiction
Conformer generation is disallowed since too many atoms, too flexible, too many undefined stereo centers
SVG Image
IUPAC Condensed
H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2
Sequence
YADAXFXNSYRKVLGQLSARKLLQDXMSR
HELM
PEPTIDE1{(Y,[dY]).(A,[dA]).(D,[dD]).(A,[dA]).[*C(=O)C(C(C)CC)N* |$_R2;;;;;;;;;_R1$|].(F,[dF]).[*C(=O)C(C(C)O)N* |$_R2;;;;;;;;_R1$|].(N,[dN]).(S,[dS]).(Y,[dY]).(R,[dR]).(K,[dK]).(V,[dV]).(L,[dL]).G.(Q,[dQ]).(L,[dL]).(S,[dS]).(A,[dA]).(R,[dR]).(K,[dK]).(L,[dL]).(L,[dL]).(Q,[dQ]).(D,[dD]).[*C(=O)C(C(C)CC)N* |$_R2;;;;;;;;;_R1$|].(M,[dM]).(S,[dS]).(R,[dR]).[am]}$$$$V2.0
IUPAC
DL-tyrosyl-DL-alanyl-DL-alpha-aspartyl-DL-alanyl-DL-isoleucyl-DL-phenylalanyl-DL-threonyl-DL-asparagyl-DL-seryl-DL-tyrosyl-DL-arginyl-DL-lysyl-DL-valyl-DL-leucyl-glycyl-DL-glutaminyl-DL-leucyl-DL-seryl-DL-alanyl-DL-arginyl-DL-lysyl-DL-leucyl-DL-leucyl-DL-glutaminyl-DL-alpha-aspartyl-DL-isoleucyl-DL-methionyl-DL-seryl-DL-argininamide
4-[[1-[[1-[[1-[[1-[[4-amino-1-[[1-[[1-[[1-[[6-amino-1-[[1-[[1-[[2-[[5-amino-1-[[1-[[1-[[1-[[1-[[6-amino-1-[[1-[[1-[[5-amino-1-[[1-[[1-[[1-[[1-[(1-amino-5-carbamimidamido-1-oxopentan-2-yl)amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoylamino]-4-oxobutanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C149H246N44O42S/c1-20-77(13)116(191-122(211)81(17)168-132(221)104(66-113(204)205)178-121(210)79(15)167-123(212)88(152)62-84-39-43-86(198)44-40-84)145(234)185-102(63-83-32-23-22-24-33-83)138(227)193-118(82(18)197)146(235)186-103(65-111(155)202)137(226)189-108(71-196)142(231)182-101(64-85-41-45-87(199)46-42-85)136(225)175-93(38-31-56-165-149(161)162)126(215)174-91(35-26-28-53-151)131(220)190-115(76(11)12)143(232)184-97(58-72(3)4)124(213)166-68-112(203)170-94(47-49-109(153)200)128(217)180-100(61-75(9)10)135(224)188-106(69-194)140(229)169-80(16)120(209)172-92(37-30-55-164-148(159)160)125(214)173-90(34-25-27-52-150)127(216)179-99(60-74(7)8)134(223)181-98(59-73(5)6)133(222)176-95(48-50-110(154)201)129(218)183-105(67-114(206)207)139(228)192-117(78(14)21-2)144(233)177-96(51-57-236-19)130(219)187-107(70-195)141(230)171-89(119(156)208)36-29-54-163-147(157)158/h22-24,32-33,39-46,72-82,88-108,115-118,194-199H,20-21,25-31,34-38,47-71,150-152H2,1-19H3,(H2,153,200)(H2,154,201)(H2,155,202)(H2,156,208)(H,166,213)(H,167,212)(H,168,221)(H,169,229)(H,170,203)(H,171,230)(H,172,209)(H,173,214)(H,174,215)(H,175,225)(H,176,222)(H,177,233)(H,178,210)(H,179,216)(H,180,217)(H,181,223)(H,182,231)(H,183,218)(H,184,232)(H,185,234)(H,186,235)(H,187,219)(H,188,224)(H,189,226)(H,190,220)(H,191,211)(H,192,228)(H,193,227)(H,204,205)(H,206,207)(H4,157,158,163)(H4,159,160,164)(H4,161,162,165)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
WGWPRVFKDLAUQJ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCSC)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC3=CC=C(C=C3)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C149H246N44O42S
Computed by PubChem 2.2 (PubChem release 2021.10.14)
86168-78-7
- Geref
- GHRH(1-29)NH2
- GRF(1-29)NH2
- Growth Hormone-Releasing Factor(1-29)Amide
- hGHRH(1-29)NH2
- Sermorelin
- Sermorelin Acetate
- Somatotropin-Releasing-Hormone(1-29)Amide
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
3357.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-12.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
52
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
49
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
118
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
3356.8220541 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
3355.8186992 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
1470 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
236
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
7640
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
31
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
-0.33
9.99
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Sermorelin (annotation moved to)
Gene Count
For the treatment of dwarfism, prevention of HIV-induced weight loss
Sermorelin is used in the treatment of children with growth hormone deficiency or growth failure. Geref increases plasma growth hormone (GH) concentration by stimulating the pituitary gland to release GH. Geref is similar to the full-length native hormone (44 residues) in its ability to stimulate GH secretion in humans.
11-12 min
Sermorelin binds to the growth hormone releasing hormone receptor and mimics native GRF in its ability to stimulate growth hormone secretion.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=WGWPRVFKDLAUQJ-UHFFFAOYSA-N
- ChEBI
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useSermorelinhttps://www.drugbank.ca/drugs/DB00010
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citing
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- PharmGKBLICENSEPharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).https://www.pharmgkb.org/page/policies
- Springer Nature
- WHO Anatomical Therapeutic Chemical (ATC) ClassificationLICENSEUse of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.https://www.whocc.no/copyright_disclaimer/
- WikipediaSermorelinhttps://en.wikipedia.org/wiki/Sermorelin
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.html
- PubChem
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- PATENTSCOPE (WIPO)SID 389158119https://pubchem.ncbi.nlm.nih.gov/substance/389158119
CONTENTS