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Structure Database (LMSD)

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Common Name

Helvolic acid

Systematic Name

(4α,6β,8α,9β,13α,14β,16β,17β)-6,16- bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid

Synonyms

LM ID

LMPR0106080005

Formula

C₃₃H₄₄O₈

Exact Mass

Calculate m/z

568.303621

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Helvolic acid is a mycotoxin originally isolated from A. fumigatus that has broad-spectrum antibiotic activity against Gram-positive and Gram-negative bacteria.^1,2 At 4-16 mg/L, it acted synergistically with erythromycin (500-2,000 mg/L) in vitro on five multi-drug resistant strains of S. aureus.³ At 10 mg/kg/d, it reduced tumor growth and prolonged survival synergistically with cyclophosphamide (20 mg/kg/d) in a mouse model of sarcoma but had no effect when administered alone.⁴

This information has been provided by Cayman Chemical

References

4. Xiao, J.-H., Zhang, Y., Liang, G.-Y., et al. Synergistic antitumor efficacy of antibacterial helvolic acid from Cordyceps taii and cyclophosphamide in a tumor mouse model. Exp. Biol. Med. (Maywood) 242(2), 214-222 (2017).

1. Chain, E., Florey, H.W., Jennings, M.A., et al. Helvolic acid, an antibiotic produced by Apergillus funigatus, mut. helvola Yuill. Br. J. Exp. Pathol. 24(3), 108-119 (1943).

2. Qin, L., Li, B., Guan, J., et al. In vitro synergistic antibacterial activities of helvolic acid on multi-drug resistant Staphylococcus aureus. Nat. Prod. Res. 23(4), 309-318 (2009).

3. Ratnaweera, P.B., Williams, D.E., de Silva, E.D., et al. Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka. Mycology 5(1), 23-28 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Aspergillus fumigatus (#746128)

Eurotiomycetes (#147545)

Stereochemistry of helvolic acid.,
Tetrahedron Lett, 1967

Pubmed ID: 6046345

String Representations

InChiKey (Click to copy)

MDFZYGLOIJNNRM-OAJDADRGSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1=CC(=O)[C@@H](C)[C@]2([H])[C@H](OC(C)=O)C(=O)[C@@]3(C)[C@]([H])([C@]21C)CC[C@@]1([H])/C(=C(/C(O)=O)\CC/C=C(\C)/C)/[C@@H](OC(C)=O)C[C@@]13C