Fumiquinazoline

Fumiquinazoline

Fumiquinazoline C
Identifiers
CAS Number
  • A: 140715-85-1 ☒N
  • B: 140852-71-7[1] ☒N
  • C: 140924-01-2[1] ☒N
  • D: 140715-86-2[1] ☒N
  • E: 140715-87-3[1] ☒N
  • F 169626-35-1 I 278184-56-8
3D model (JSmol)
  • A: Interactive image
  • B: Interactive image
  • C: Interactive image
  • D: Interactive image
  • E: Interactive image
ChEBI
  • A: CHEBI:64546
  • C: CHEBI:64551
ChEMBL
  • A: ChEMBL2229120
  • D: ChEMBL2229119
KEGG
  • C: C22148
  • D: C22149
PubChem CID
  • A: 11247802
  • B: 15224332
  • C: 11339719
  • D: 9980845
  • E: 10027910
CompTox Dashboard (EPA)
  • B: DTXSID101017926
  • C: DTXSID80893275
  • E: DTXSID401017937
InChI
  • A: InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13-,18+,23-,24-/m0/s1
    Key: DQQCCKFZJNINST-VCPZKGNQSA-N
  • B: InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13+,18-,23+,24+/m1/s1
    Key: DQQCCKFZJNINST-ZRCGILORSA-N
  • C: InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(22(28)25-12)11-17-18(30)27-23(2,33-24)21-26-15-9-5-3-7-13(15)20(32)29(17)21/h3-10,12,17,22,25H,11H2,1-2H3,(H,27,30)/t12-,17+,22-,23-,24-/m0/s1
    Key: POEYRUBMWIOMTB-LTQSKDJASA-N
  • D: InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(33)11-17-18(30)26-23(2,29(12)22(24)28)21-25-15-9-5-3-7-13(15)20(32)27(17)21/h3-10,12,17,22,33H,11H2,1-2H3,(H,26,30)/t12-,17+,22+,23-,24-/m0/s1
    Key: YYLAARMDRFESOL-CVAYNVNESA-N
  • E: InChI=1S/C25H25N5O5/c1-13-20(32)29-17-11-7-5-9-15(17)25(34,23(29)26-13)12-18-19(31)28-24(2,35-3)22-27-16-10-6-4-8-14(16)21(33)30(18)22/h4-11,13,18,23,26,34H,12H2,1-3H3,(H,28,31)/t13-,18+,23-,24+,25-/m0/s1
    Key: MUUBSMIWCJLEGK-HBLJGDDGSA-N
  • A: C[C@H]1C2=NC3=CC=CC=C3C(=O)N2[C@@H](C(=O)N1)C[C@]4([C@H]5N[C@H](C(=O)N5C6=CC=CC=C64)C)O
  • B: C[C@@H]1C2=NC3=CC=CC=C3C(=O)N2[C@@H](C(=O)N1)C[C@]4([C@H]5N[C@H](C(=O)N5C6=CC=CC=C64)C)O
  • C: C[C@H]1C(=O)N2[C@H](N1)[C@]3(C[C@@H]4C(=O)N[C@@](O3)(C5=NC6=CC=CC=C6C(=O)N45)C)C7=CC=CC=C72
  • D: C[C@H]1C(=O)N2[C@@H]3N1[C@]4(C5=NC6=CC=CC=C6C(=O)N5[C@H](C[C@@]3(C7=CC=CC=C72)O)C(=O)N4)C
  • E: C[C@H]1C(=O)N2[C@H](N1)[C@@](C3=CC=CC=C32)(C[C@@H]4C(=O)N[C@](C5=NC6=CC=CC=C6C(=O)N45)(C)OC)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Fumiquinazolines are bio-active isolates of Aspergillus.[2][3]

References

  1. ^ a b c d Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 793. ISBN 978-1-4200-7770-4.
  2. ^ Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (2010). Dictionary of Alkaloids, Second Edition with CD-ROM. CRC Press. ISBN 9781420077704.
  3. ^ Walsh, Christopher T.; Tang, Yi (2017). Natural Product Biosynthesis: Chemical Logic and Enzymatic Machinery. Royal Society of Chemistry. ISBN 9781788010764.

Further reading

  • Cheng, Zhongbin; Lou, Lanlan; Liu, Dong; Li, Xiaodan; Proksch, Peter; Yin, Sheng; Lin, Wenhan (10 November 2016). "Versiquinazolines A–K, Fumiquinazoline-Type Alkaloids from the Gorgonian-Derived Fungus Aspergillus versicolor LZD-14-1". Journal of Natural Products. 79 (11): 2941–2952. doi:10.1021/acs.jnatprod.6b00801. PMID 27933898.
  • Ames, BD; Haynes, SW; Gao, X; Evans, BS; Kelleher, NL; Tang, Y; Walsh, CT (11 October 2011). "Complexity generation in fungal peptidyl alkaloid biosynthesis: oxidation of fumiquinazoline A to the heptacyclic hemiaminal fumiquinazoline C by the flavoenzyme Af12070 from Aspergillus fumigatus". Biochemistry. 50 (40): 8756–69. doi:10.1021/bi201302w. PMC 3194008. PMID 21899262.
  • Magotra, A; Kumar, M; Kushwaha, M; Awasthi, P; Raina, C; Gupta, AP; Shah, BA; Gandhi, SG; Chaubey, A (December 2017). "Epigenetic modifier induced enhancement of fumiquinazoline C production in Aspergillus fumigatus (GA-L7): an endophytic fungus from Grewia asiatica L". AMB Express. 7 (1): 43. doi:10.1186/s13568-017-0343-z. PMC 5315648. PMID 28213885.
  • New metabolites from the marine-derived fungus Aspergillus fumigatus
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