Duclauxin

Duclauxin
Identifiers
CAS Number	1732-37-2;
3D model (JSmol)	Interactive image;
ChemSpider	68003973;
PubChem CID	10482567;
UNII	Y76N2QE4RZ ;
	InChI InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3/t21-,24+,25+,28-,29+/m0/s1 Key: WBQDAYWQELBEPU-FTAQWXBTSA-N;
	SMILES CC1=CC(=C2C3=C1C(=O)[C@H]4[C@H]([C@]3(COC2=O)[C@@H]5[C@]4(C6=C7C(=COC(=O)C7=C(C=C6C)O)C5=O)OC)OC(=O)C)O;
Properties
Chemical formula	C29H22O11
Molar mass	546.484 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Duclauxin is a chemical compound isolated from Penicillium duclauxi.^[1]

Other chemical compounds which are derivatives of duclauxin are known,^[2] such as cryptoclauxin, bacillisporins, and talaromycesones. They are sometimes referred to collectively as duclauxins.^[3]

Cryptoclauxin
Bacillisporin C
Bacillisporin F
Talaromycesone B

Notes

^ Kuhr, I; Fuska, J; Sedmera, P; Podojil, M; Vokoun, J; Vanĕk, Z (1973). "An antitumor antibiotic produced by Penicillium stipitatum Thom; its identity with duclauxin". The Journal of Antibiotics. 26 (9): 535–6. doi:10.7164/antibiotics.26.535. PMID 4799788.
^ Shahid, Hamza; Cai, Teng; Wang, Yuyang; Zheng, Caiqing; Yang, Yuting; Mao, Ziling; Ding, Ping; Shan, Tijiang (2021). "Duclauxin Derivatives from Fungi and Their Biological Activities". Frontiers in Microbiology. 12. doi:10.3389/fmicb.2021.766440. PMC 8727740.
^ Gao, Shu-Shan; Zhang, Tao; Garcia-Borràs, Marc; Hung, Yiu-Sun; Billingsley, John M.; Houk, K. N.; Hu, Youcai; Tang, Yi (2018). "Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide". Journal of the American Chemical Society. 140 (22): 6991–6997. doi:10.1021/jacs.8b03705. PMC 6309916. PMID 29741874.

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[1] Kuhr, I; Fuska, J; Sedmera, P; Podojil, M; Vokoun, J; Vanĕk, Z (1973). "An antitumor antibiotic produced by Penicillium stipitatum Thom; its identity with duclauxin". The Journal of Antibiotics. 26 (9): 535–6. doi:10.7164/antibiotics.26.535. PMID 4799788.

[2] Shahid, Hamza; Cai, Teng; Wang, Yuyang; Zheng, Caiqing; Yang, Yuting; Mao, Ziling; Ding, Ping; Shan, Tijiang (2021). "Duclauxin Derivatives from Fungi and Their Biological Activities". Frontiers in Microbiology. 12. doi:10.3389/fmicb.2021.766440. PMC 8727740.

[3] Gao, Shu-Shan; Zhang, Tao; Garcia-Borràs, Marc; Hung, Yiu-Sun; Billingsley, John M.; Houk, K. N.; Hu, Youcai; Tang, Yi (2018). "Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide". Journal of the American Chemical Society. 140 (22): 6991–6997. doi:10.1021/jacs.8b03705. PMC 6309916. PMID 29741874.

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Identifiers

CAS Number	1732-37-2
3D model (JSmol)	Interactive image
ChemSpider	68003973
PubChem CID	10482567
UNII	Y76N2QE4RZ^Y
InChI InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3/t21-,24+,25+,28-,29+/m0/s1 Key: WBQDAYWQELBEPU-FTAQWXBTSA-N
SMILES CC1=CC(=C2C3=C1C(=O)[C@H]4[C@H]([C@]3(COC2=O)[C@@H]5[C@]4(C6=C7C(=COC(=O)C7=C(C=C6C)O)C5=O)OC)OC(=O)C)O
Properties
Chemical formula	C₂₉H₂₂O₁₁
Molar mass	546.484 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references