Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H44O8 |
Molecular Weight | 568.6977 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@]3([H])[C@@]4(C)C=CC(=O)[C@@H](C)[C@]4([H])[C@H](OC(C)=O)C(=O)[C@]3(C)[C@@]1(C)C[C@H](OC(C)=O)\C2=C(\CCC=C(C)C)C(O)=O
InChI
InChIKey=MDFZYGLOIJNNRM-OAJDADRGSA-N
InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
Molecular Formula | C33H44O8 |
Molecular Weight | 568.6977 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24772371Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/27876600
https://www.ncbi.nlm.nih.gov/pubmed/27373660
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24772371
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/27876600
https://www.ncbi.nlm.nih.gov/pubmed/27373660
Helvolic acid is a mycotoxin with antibacterial activity that shows broad activity against Gram positive and negative bacteria. For example Helvolic acid showed potent inhibitory effects against Staphylococcus aureus and Pseudomonas aeruginosa with MIC (minimum inhibitory concentration) values of 5.8 and 4.6ug/mL, respectively. It is a steroidal triterpene that is an inhibitor of the protein biosynthesis through archeal EF-2 (elongation factor 2). Shows antioxidant effects. Helvolic acid also showed in vitro antitrypanosomal activity against Trypanosoma brucei brucei. It showed inhibitory activity against Candida albicans and Plasmodium falciparum.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL352 |
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Target ID: CHEMBL348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27876600 |
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Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27373660 |
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Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738405 |
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Target ID: CHEMBL359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24772371 |
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Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15522437 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka. | 2014 Mar |
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In Vitro Antitrypanosomal Activity of the Secondary Metabolites from the Mutant Strain IU-3 of the Insect Pathogenic Fungus Ophiocordyceps coccidiicola NBRC 100683. | 2016 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27604096
Doses of 10 and 20 mg/kg/day helvolic acid did not exert significant antitumor activity. Co-administration of 10 mg/kg/day helvolic acid and 20 mg/kg/day cyclophosphamide (CTX) - showed promising antitumor activity
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15522437
Helvolic acid was shown to inhibit C. albicans with MIC 31.5 ug/mL
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:44:07 GMT 2023
by
admin
on
Fri Dec 15 19:44:07 GMT 2023
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Record UNII |
MZX54GS8AH
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Record Status |
Validated (UNII)
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Record Version |
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