Geclosporin
PubChem CID
6475296
Structure
Molecular Formula
Synonyms
- Cyclosporin G
- Geclosporin
- 74436-00-3
- cyclosporine G
- Geclosporin [INN]
Molecular Weight
1216.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2006-04-29
- Modify:2025-01-04
Description
Geclosporin has been reported in Trichoderma polysporum and Tolypocladium inflatum with data available.
Chemical Structure Depiction
Conformer generation is disallowed since too many atoms, too flexible
SVG Image
IUPAC Condensed
cyclo[Ala-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-N(Me)Bmt(E)-Nva-Sar-N(Me)Leu-Val-N(Me)Leu]
HELM
PEPTIDE1{A.[dA].[meL].[meL].[meV].[*C(=O)[C@H]([C@@H]([C@H](C)C/C=C/C)O)N(*)C |$_R2;;;;;;;;;;;;;_R1;$|].[Nva].[Sar].[meL].V.[meL]}$PEPTIDE1,PEPTIDE1,11:R2-1:R1$$$
IUPAC
cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-N-methyl-(4R)-4-[(E)-but-2-enyl]-4-methyl-L-threonyl-L-norvalyl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl]
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C63H113N11O12/c1-25-27-29-41(15)53(76)52-57(80)66-44(28-26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27,35-48,50-53,76H,26,28-34H2,1-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b27-25+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
ZMKGDQSIRSGUDJ-VSROPUKISA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CCC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C63H113N11O12
Computed by PubChem 2.2 (PubChem release 2021.10.14)
74436-00-3
- 2-norVal-cyclosporin
- 2-norvalyl-cyclosporin
- 7-L-norvaline-cyclosporin A
- cyclosporin G
- cyclosporin, 2-norvaline-
- cyclosporin, norVal(2)-
- cyclosporine G
- norvaline(2)-cyclosporine
- NVa(2)-cyclosporin
- OG 37-325
- OG37-325
- Cyclosporin G
- Geclosporin
- 74436-00-3
- cyclosporine G
- Geclosporin [INN]
- Cyclosporin-g
- 2-norVal-cyclosporin
- Cyclosporin A, 7-L-norvaline-
- UNII-UA3JNW70T9
- UA3JNW70T9
- (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- SDZ-37-325
- CYCLOSPORIN G [MI]
- OG-37-325
- Cyclo(((2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl)-L-norvalyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl)
- CYCLO((2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL-L-NORVALYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL-L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL)
- CYCLO(L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL-(3R,4R,6E)-6,7-DIDEHYDRO-3-HYDROXY-N,4-DIMETHYL-L-2-AMINOOCTANOYL-L-NORVALYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)
- NVa(2)-cyclosporin
- 2-norvalyl-cyclosporin
- norvaline(2)-cyclosporine
- cyclosporin, 2-norvaline-
- cyclosporin, norVal(2)-
- geclosporina
- geclosporine
- geclosporinum
- 7-L-norvaline-cyclosporin A
- (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-((E,1R,2R)-1-hydroxy-2-methylhex-4-enyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- OG37-325
- OG 37-325
- SCHEMBL2110698
- CHEMBL2107422
- ZMKGDQSIRSGUDJ-VSROPUKISA-N
- EX-A2493
- SDZ37325
- BDBM50422041
- OG37325
- BC171087
- HY-105023
- CS-0024720
- Q27290967
- (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
1216.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
7.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
16
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
1215.85701808 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
1215.85701808 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
279 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
86
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
2340
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
12
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
1
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)
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
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Immunosuppressive Agents
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=ZMKGDQSIRSGUDJ-VSROPUKISA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jspcyclosporin Ghttps://ctdbase.org/detail.go?type=chem&acc=C045571
- Japan Chemical Substance Dictionary (Nikkaji)
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Geclosporinhttps://www.wikidata.org/wiki/Q27290967LOTUS Treehttps://lotus.naturalproducts.net/
- 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-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Springer Nature
- Wikidatageclosporinhttps://www.wikidata.org/wiki/Q27290967
- PubChem
- 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.htmlcyclosporin Ghttps://www.ncbi.nlm.nih.gov/mesh/67045571Immunosuppressive Agentshttps://www.ncbi.nlm.nih.gov/mesh/68007166
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388433067https://pubchem.ncbi.nlm.nih.gov/substance/388433067
CONTENTS