HELVOLIC ACID

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27876600 \| https://www.ncbi.nlm.nih.gov/pubmed/24772371	Inhibitor 8297
Pseudomonas aeruginosa 12 Target ID: CHEMBL348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27876600	Inhibitor 8297
Trypanosoma brucei brucei 12 Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27373660	Inhibitor 8297
Plasmodium falciparum 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738405	Inhibitor 8297
Bacillus subtilis 8 Target ID: CHEMBL359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24772371	Inhibitor 8297
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15522437	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738405	Curative	Basic research	Unknown Approved Use Unknown
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27373660	Curative	Basic research	Unknown Approved Use Unknown
Pseudomonas aeruginosa infection 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27876600	Curative	Basic research	Unknown Approved Use Unknown
Staphylococcus aureus infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27876600 https://www.ncbi.nlm.nih.gov/pubmed/24772371	Curative	Basic research	Unknown Approved Use Unknown
Candida infections 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15522437	Curative	Basic research	Unknown Approved Use Unknown

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	24772371
In Vitro Antitrypanosomal Activity of the Secondary Metabolites from the Mutant Strain IU-3 of the Insect Pathogenic Fungus Ophiocordyceps coccidiicola NBRC 100683.	2016	27373660

Patents

Sample Use Guides

In Vivo Use Guide

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

Helvolic acid was shown to inhibit C. albicans with MIC 31.5 ug/mL

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:44:07 GMT 2023` Edited by `admin` on `Fri Dec 15 19:44:07 GMT 2023`
Record UNII	MZX54GS8AH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HELVOLIC ACID

Common Name

English

FUMIGACIN

Common Name

English

29-NORDAMMARA-1,17(20),24-TRIEN-21-OIC ACID, 6,16-BIS(ACETYLOXY)-3,7-DIOXO-, (4.ALPHA.,6.BETA.,8.ALPHA.,9.BETA.,13.ALPHA.,14.BETA.,16.BETA.,17Z)-

Common Name

English

HELVOLIC ACID [MI]

Common Name

English

(Z)-6.BETA.,16.BETA.-DIHYDROXY-3,7-DIOXO-29-NOR-8.ALPHA.,9.BETA.,13.ALPHA.,14.BETA.-DAMMARA-1,17(20),24-TRIEN-21-OIC ACID DIACETATE

Common Name

English

NSC-319943

Code

English

Code System Code Type Description

NSC

319943