Geclosporin
Basic information
- CAS
74436-00-3- Standard SMILES
C/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](CCC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C- InChIKey
ZMKGDQSIRSGUDJ-VSROPUKISA-N- Molecular formula
- C63H113N11O12
- Average molar mass
- 1,216.6 g/mol
- Monoisotopic mass
- 1,215.85701808
Overview
geclosporin has been reported in Trichoderma polysporum and Tolypocladium inflatum with data available.
Names & identifiers
- Preferred name
- Geclosporin
- IUPAC
- (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
- English name
- Geclosporin
- Molecular formula
- C63H113N11O12
- Molecular weight
- 1216.64
Names & synonyms
Cyclosporin GGeclosporin74436-00-3cyclosporine GCyclosporin-g2-norVal-cyclosporingeclosporinageclosporineCyclosporin A, 7-L-norvaline-UA3JNW70T9SDZ37325(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
Show more names
CS-2592Cyclosporin G (9CI)Cyclosporin Impurity GCyclosporine Impurity GCyclosporine Impurity 7Ring spore fungus element
SDZ-37-325OG37325OG-37-325NVa(2)-cyclosporin2-norvalyl-cyclosporinnorvaline(2)-cyclosporinecyclosporin, 2-norvaline-cyclosporin, norVal(2)-
Properties
Computed structural properties
- XLogP
- 7.9
- Topological polar surface area
- 279 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 16
- Heavy atoms
- 86
- Formal charge
- 0
- Complexity
- 2,340
Physicochemical properties
- Melting point
- 196 · 196-197°
- alpha
- 20 · D20 -245° (c = 1.0 in chloroform); D20 -191° (c = 1.04 in methanol)
- Boiling point
- 1297.8 · 1297.8±65.0 °C(Predicted)
- Density
- 1.013 · 1.013±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 13.32 · 13.32±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability
- Hygroscopic
- InChIKey
- ZMKGDQSIRSGUDJ-LIAWPGETNA-N
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 JNW70T9 · UA3JNW70T9
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Applications
UsesCylclosporin G is a derivative of Cyclosporin A, an immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection. A group of nonpolar cyclic oligopeptides with immunosupppressant activity.
UsesCylclosporin G is a derivative of Cyclosporin A (C989900), an immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection. A group of nonpolar cyclic oligopeptides with immunosupppressant activity.
Related reactions
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Compound notes
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