Fumiquinazoline

Fumiquinazoline
	; Fumiquinazoline C
Identifiers
CAS Number	A: 140715-85-1 ; B: 140852-71-7 ; C: 140924-01-2 ; D: 140715-86-2 ; E: 140715-87-3 ; 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;
	SMILES 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

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

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[1]
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.

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.

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[doa-1] [1]
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] [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] [3]
Walsh, Christopher T.; Tang, Yi (2017). Natural Product Biosynthesis: Chemical Logic and Enzymatic Machinery. Royal Society of Chemistry. ISBN 9781788010764.

[2]

[3]

[1]

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Fumiquinazoline

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References

Further reading

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Identifiers
Fumiquinazoline C
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
SMILES 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