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Sordarin

CAT: 0013-GTR19279313-02Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19279313-02Size:50 mg
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Description
Sordarin (Compound 1) is an antifungal agent that targets elongation factor 2 (EF2) and features a tetracyclic diterpene core with a norbornene system. It can be isolated from the fungus Sordaria araneosa. Sordarin exhibits potent antifungal activity against Saccharomyces cerevisiae and Candida albicans. By stabilizing the ribosome/EF2 complex, Sordarin blocks ribosomal translocation along mRNA during nascent polypeptide chain elongation, thereby inhibiting fungal protein synthesis.
CAS Number
11076-17-8
Smiles
C (O) (=O) [C@]12[C@@]3 (CO[C@H]4[C@@H] (O) [C@H] (O) [C@H] (OC) [C@@H] (C) O4) [C@] (C[C@]1 (C=O) [C@]5 ([C@] (C3) ([C@H] (C) CC5) [H]) [H]) (C=C2C (C) C) [H]
Molecular Formula
C27H40O8
Molecular Weight
492.61
Notes
For research use only.

Chemical Information

Sordarin

Sordarin is an antifungal metabolite of Sordaria araneosa that inhibits protein synthesis. It has a tetracyclic diterpene glycoside structure. It has a role as an antifungal agent and a protein synthesis inhibitor. It is a glycoside, a tetracyclic diterpenoid and a monosaccharide derivative.

CAS Number11076-17-8
PubChem CID485851
IUPAC Name(1R,2S,4R,5R,8R,9S,11R)-2-[[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxymethyl]-9-formyl-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
Molecular FormulaC27H40O8
Molecular Weight492.6
XLogP1.5
Topological Polar Surface Area123
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Heavy Atom Count35
Formal Charge0
Complexity917
SMILES
C[C@@H]1CC[C@@H]2[C@@H]1C[C@@]3([C@@H]4C[C@]2([C@]3(C(=C4)C(C)C)C(=O)O)C=O)CO[C@H]5[C@H]([C@@H]([C@@H]([C@H](O5)C)OC)O)O
InChI
InChI=1S/C27H40O8/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32)/t14-,15-,16+,17-,18-,20+,21+,22-,23-,25+,26+,27+/m1/s1
InChIKey
OGGVRVMISBQNMQ-YPBSLCSMSA-N
Chemical Structure
2D Structure
2D structure of Sordarin
CAS: 11076-17-8
CID: 485851
Formula: C27H40O8
MW: 492.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight492.6
XLogP31.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass492.27231823
Monoisotopic Mass492.27231823
Topological Polar Surface Area123 Ų
Heavy Atom Count35
Formal Charge0
Complexity917
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

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