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Glepaglutide

PubChem CID
146170995
Structure
Glepaglutide_small.png
Molecular Formula
Synonyms
  • Glepaglutide
  • ZP1848
  • Glepaglutide (USAN)
  • ZP-1848
  • GLEPAGLUTIDE [USAN]
Molecular Weight
4316 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2020-06-20
  • Modify:
    2025-01-18
Description
Glepaglutide is under investigation in clinical trial NCT00868660 (Healthy Normal Single Ascending Dose and Crohn's Patient Multiple Ascending Dose).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Glepaglutide.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-His-Gly-Glu-Gly-Thr-Phe-Ser-Ser-Glu-Leu-Ala-Thr-Ile-Leu-Asp-Ala-Leu-Ala-Ala-Arg-Asp-Phe-Ile-Ala-Trp-Leu-Ile-Ala-Thr-Lys-Ile-Thr-Asp-Lys-Lys-Lys-Lys-Lys-Lys-NH2
Sequence
HGEGTFSSELATILDALAARDFIAWLIATKITDKKKKKK
PLN
H-HGEGTFSSELATILDALAARDFIAWLIATKITDKKKKKK-[NH2]
HELM
PEPTIDE1{H.G.E.G.T.F.S.S.E.L.A.T.I.L.D.A.L.A.A.R.D.F.I.A.W.L.I.A.T.K.I.T.D.K.K.K.K.K.K.[am]}$$$$
IUPAC
L-histidyl-glycyl-L-alpha-glutamyl-glycyl-L-threonyl-L-phenylalanyl-L-seryl-L-seryl-L-alpha-glutamyl-L-leucyl-L-alanyl-L-threonyl-L-isoleucyl-L-leucyl-L-alpha-aspartyl-L-alanyl-L-leucyl-L-alanyl-L-alanyl-L-arginyl-L-alpha-aspartyl-L-phenylalanyl-L-isoleucyl-L-alanyl-L-tryptophyl-L-leucyl-L-isoleucyl-L-alanyl-L-threonyl-L-lysyl-L-isoleucyl-L-threonyl-L-alpha-aspartyl-L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-lysinamide

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(4S)-5-[[2-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-6-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-4-[[2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]acetyl]amino]-5-oxopentanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

3.1.2 InChI

InChI=1S/C197H325N53O55/c1-27-102(13)152(190(299)220-111(22)166(275)248-157(113(24)254)194(303)230-129(66-45-52-78-204)176(285)244-155(105(16)30-4)192(301)250-158(114(25)255)195(304)240-142(90-151(267)268)183(292)228-128(65-44-51-77-203)173(282)227-127(64-43-50-76-202)172(281)226-126(63-42-49-75-201)171(280)225-125(62-41-48-74-200)170(279)224-124(61-40-47-73-199)169(278)222-123(160(206)269)60-39-46-72-198)245-185(294)136(83-101(11)12)234-182(291)139(86-118-91-211-122-59-38-37-58-120(118)122)232-164(273)109(20)219-189(298)153(103(14)28-2)246-186(295)138(85-117-56-35-32-36-57-117)235-184(293)141(89-150(265)266)236-174(283)130(67-53-79-210-197(207)208)223-162(271)107(18)215-161(270)106(17)216-177(286)133(80-98(5)6)231-163(272)108(19)217-179(288)140(88-149(263)264)237-180(289)135(82-100(9)10)238-191(300)154(104(15)29-3)247-196(305)159(115(26)256)249-165(274)110(21)218-178(287)134(81-99(7)8)233-175(284)132(69-71-148(261)262)229-187(296)143(95-251)242-188(297)144(96-252)241-181(290)137(84-116-54-33-31-34-55-116)239-193(302)156(112(23)253)243-146(258)94-213-168(277)131(68-70-147(259)260)221-145(257)93-212-167(276)121(205)87-119-92-209-97-214-119/h31-38,54-59,91-92,97-115,121,123-144,152-159,211,251-256H,27-30,39-53,60-90,93-96,198-205H2,1-26H3,(H2,206,269)(H,209,214)(H,212,276)(H,213,277)(H,215,270)(H,216,286)(H,217,288)(H,218,287)(H,219,298)(H,220,299)(H,221,257)(H,222,278)(H,223,271)(H,224,279)(H,225,280)(H,226,281)(H,227,282)(H,228,292)(H,229,296)(H,230,303)(H,231,272)(H,232,273)(H,233,284)(H,234,291)(H,235,293)(H,236,283)(H,237,289)(H,238,300)(H,239,302)(H,240,304)(H,241,290)(H,242,297)(H,243,258)(H,244,285)(H,245,294)(H,246,295)(H,247,305)(H,248,275)(H,249,274)(H,250,301)(H,259,260)(H,261,262)(H,263,264)(H,265,266)(H,267,268)(H4,207,208,210)/t102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112+,113+,114+,115+,121-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,152-,153-,154-,155-,156-,157-,158-,159-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.3 InChIKey

DOAUQKRTILFGHV-PDCMDPCFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.4 SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CC5=CNC=N5)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C197H325N53O55
Computed by PubChem 2.1 (PubChem release 2021.05.07)

3.3 Other Identifiers

3.3.1 CAS

914009-86-2

3.3.2 DrugBank ID

3.3.3 NCI Thesaurus Code

3.3.4 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
4316 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-19
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
62
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
65
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
151
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
4315.4330713 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
4313.4263617 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
1770 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
305
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
10200
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
45
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
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 2019.06.18)

4.2 Chemical Classes

4.2.1 Drugs

4.2.1.1 Human Drugs
Paediatric drug

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Treatment of short bowel syndrome

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 EU Clinical Trials Register

7.3 EMA Drug Information

Type
Paediatric investigation
Active Substance
Therapeutic Area
Gastroentology-Hepatology
Drug Form
Solution for injection
Administration Route
Subcutaneous use
Decision Type
P: decision agreeing on a investigation plan, with or without partial waiver(s) and or deferral(s)
Decision Date
2021-10-29

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Human Drugs -> EU pediatric investigation plans

9 Associated Disorders and Diseases

10 Literature

10.1 Chemical Co-Occurrences in Literature

10.2 Chemical-Gene Co-Occurrences in Literature

10.3 Chemical-Disease Co-Occurrences in Literature

11 Classification

11.1 NCI Thesaurus Tree

11.2 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  2. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  3. EU Clinical Trials Register
  4. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  5. NCI Thesaurus (NCIt)
    LICENSE
    Unless 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
  6. Therapeutic Target Database (TTD)
  7. Wikidata
  8. PubChem
  9. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS