Compound ID | 1970

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Helvolic acid

Synonym(s): Fumigacin

Class: Fusidane

Spectrum of activity: Gram-positive
Details of activity: Inhibits the function of elongation factor G (EF-G), leading to the inhibition of protein synthesis. Bacteriostatic activity against Gram-positive bacteria
Description: Natural product produced by Aspergillus and other fungi
Year first mentioned: 1943
Development status: Experimental
Chemical structure(s):
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Molecular weight: 568.7
Iso. SMILES: C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]4[C@@]3(C[C@@H](C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
InChI Key: MDFZYGLOIJNNRM-HYNRAYKSSA-N
Can. SMILES: CC(=CCCC(=C1[C@@H]2CC[C@H]3[C@@]4(C)C=CC(=O)[C@@H](C)[C@@H]4[C@@H](C(=O)[C@]3(C)[C@@]2(C)C[C@@H]1OC(=O)C)OC(=O)C)C(=O)O)C
InChI: 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)/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/Helvolic-acid
Guide to Pharmacology: helvolic acid
Citations:
  • https://pubs.acs.org/doi/10.1021/acs.jnatprod.8b00382
  • https://watermark.silverchair.com/evaa163.pdf?token=AQECAHi208BE49Ooan9kkhW_Ercy7Dm3ZL_9Cf3qfKAc485ysgAAAuEwggLdBgkqhkiG9w0BBwagggLOMIICygIBADCCAsMGCSqGSIb3DQEHATAeBglghkgBZQMEAS4wEQQMfOO3aKQlA6RjaO31AgEQgIIClOv_dSjvoI97m5UU3tBLtdpcdCN20QxXJ9uI36Nyi1r-cQU92YJJLJkDB7cFle0JVEmhH_e-u5By5dBDqwcwhMuI5UkJubwrbphUL_IZOnP-N2V6aWRpQUBRMvZ4fGJ8C93FCBojQ3wSmoO6B4zApuZN4HZbgSoTgdahzfCh37dFTwBwPCl3AcJNdOuTEWyNcCx7rlbgE6zxNh4QywlUaF7GtGivmC9h3OvttkQ65XUrMnu1Vy92xDC1KnJXkLwGzVre5uIheKaOj5Z1NYd-6n4R8T6sJRAB6RWjyMiOEGphgUKR6zfG4vadclnC2a0F-OAVG6CRs5Rr3Pd_EGp7RJTg38GVaifGWzB3F15HT3vxWjQ6ea5gcP6S4grTRz1iMY0mEthIp0yaVnQT2kj9goa27yIZ3-BefjoJUTq4-vZoG4CD9hyo7u0v5xDTNocLW1McZ8oPWstCj9m2d36MJT6OuhRRtnJJIKlC-r_OPHVNcp7B7walmt4j3NcRe2VNj7WCOjMrUI1dOgketUegKRcv9OqahBbybY3FKoJdXt0uxqTWmaofkXO3BJ73Obu6qS3kEJuGCzv3rYTGf_ary33r-c4h-GXyzog5FVCOqM_vI4aB0J5Chos3rpPTElYnKzq2CeX70PuUWZo1dwwD_Z34pVNtHtvYRba8JccuUdf835SNfTI5Nl_LIrrZ2hN32jjKXNKTgQaodE8C721hhIgzxK0c-PYXUoQ3kPwHZlWaQiuKC1d007o0g7o5WXT95xcVbf5JIEuEWNOpPA2alykyejE0XOJyfA4-XlQ4l8Qv9gu60VSkxuuOS-MXGTdX1JyPhxzSMTTeFB_eI01S22IW_IuWMx7wexdAO5nQEuBuhDTfpw
  • https://www.nature.com/articles/s41467-017-01813-9
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2065532/

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