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Hyaluromycin

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Hyaluromycin
Names
Systematic IUPAC name
(2S)-4,9,10'-Trihydroxy-N-(2-hydroxy-5-oxo-1-cyclopenten-1-yl)-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C30H21NO13/c1-41-16-8-15(34)19-20(23(16)36)25(38)27-12(22(19)35)9-30(44-27)5-4-10-6-11-7-17(28(39)31-21-13(32)2-3-14(21)33)42-29(40)18(11)24(37)26(10)43-30/h6-8,32,35,37-38H,2-5,9H2,1H3,(H,31,39)/t30-/m0/s1
    Key: SVUGCIHLYMYXQP-PMERELPUSA-N
  • InChI=1S/C30H21NO13/c1-41-16-8-15(34)19-20(23(16)36)25(38)27-12(22(19)35)9-30(44-27)5-4-10-6-11-7-17(28(39)31-21-13(32)2-3-14(21)33)42-29(40)18(11)24(37)26(10)43-30/h6-8,32,34,36-37H,2-5,9H2,1H3,(H,31,39)/t30-/m0/s1
    Key: LBCHZWBDBFDLQH-PMERELPUSA-N
  • O=C1OC(=Cc2cc3CC[C@]4(Cc5c(O4)c(O)c4C(=O)C(=CC(=O)c4c5O)OC)Oc3c(O)c12)C(=O)NC=1C(=O)CCC=1O
  • COC1=C(C2=C(C(=C1)O)C(=O)C3=C(C2=O)O[C@]4(C3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)NC7=C(CCC7=O)O)O)O
Properties
C30H21NO13
Molar mass 603.492 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hyaluromycin is a member of the rubromycin family of antibiotics that inhibits the hydrolysis of hyaluronic acid by hyaluronidase.[1] It has been isolated from cultures of Streptomyces hyaluromycini.[2]

References

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  1. ^ Harunari E, Imada C, Igarashi Y, Fukuda T, Terahara T, Kobayashi T (January 2014). "Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp". Marine Drugs. 12 (1): 491–507. doi:10.3390/md12010491. PMC 3917283. PMID 24451191.
  2. ^ Harunari E, Komaki H, Ichikawa N, Hosoyama A, Kimura A, Hamada M, Igarashi Y (January 2018). "Draft genome sequence of Streptomyces hyaluromycini MB-PO13T, a hyaluromycin producer". Standards in Genomic Sciences. 13 (2): 2. doi:10.1186/s40793-017-0286-7. PMC 5765640. PMID 29371910.