Bactobolin

Bactobolin
Names
	IUPAC name (2S)-N-[(3S,4R,4aR,5R,6R)-3-(Dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-isochromen-4-yl]-2-aminopropanamide
Identifiers
CAS Number	72615-20-4 ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:138579 ;
ChEMBL	ChEMBL489472 ;
ChemSpider	35035304 ;
PubChem CID	54676871 ;
UNII	EOF7S67HS2 ;
CompTox Dashboard (EPA)	DTXSID20222944 ;
	InChI InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1 Key: RBCHRRIVFAIGFI-RGBMRXMBSA-N;
	SMILES C[C@@H](C(=O)N[C@@H]1[C@@H]2[C@H]([C@@H](CC(=C2C(=O)O[C@]1(C)C(Cl)Cl)O)O)O)N;
Properties
Chemical formula	C14H20Cl2N2O6
Molar mass	383.22 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

Last updated June 06, 2025

Bactobolin is a cytotoxic, polyketide-peptide and antitumor antibiotic with the molecular formula C₁₄H₂₀Cl₂N₂O₆.^[2]^[3]^[4]^[5] Bactobolin was discovered in 1979.^[6]

References

1 2 "Bactobolin". Pubchem.ncbi.NLM.nih.gov.
↑ Greenberg, E. Peter; Chandler, Josephine R.; Seyedsayamdost, Mohammad R. (27 March 2020). "The Chemistry and Biology of Bactobolin: A 10-Year Collaboration with Natural Product Chemist Extraordinaire Jon Clardy". Journal of Natural Products. 83 (3): 738–743. doi:10.1021/acs.jnatprod.9b01237. hdl: 1808/32425 . PMC 8118907 . PMID 32105069.
↑ Weinreb, Steven M. (1995). "Total synthesis of the microbial antitumor antibiotics actinobolin and bactobolin". Studies in Natural Products Chemistry. 16: 3–25. doi:10.1016/S1572-5995(06)80051-7. ISBN 9780444822642.
↑ Munakata, Tomohiko; Ikeda, Yoshifumi; Matsuki, Hideo; Isagai, Katsuyoshi (May 1983). "Cultural Conditions and Strain Improvement for Production of Bactobolin". Agricultural and Biological Chemistry. 47 (5): 929–934. doi:10.1080/00021369.1983.10865772.
↑ Franco, Carlos M.; Belda, Beatriz Vázquez (2 December 2020). Natural Compounds as Antimicrobial Agents. MDPI. p. 134. ISBN 978-3-03936-048-2.
↑ Reinhoudt, D. N.; Connors, T. A.; Pinedo, H. M.; Poll, K. W. van de (6 December 2012). Structure-Activity Relationships of Anti-Tumour Agents. Springer Science & Business Media. p. 270. ISBN 978-94-009-6798-4.

Weinreb, S. M.; Garigipati, R. S. (1 January 1989). "Design of an efficient strategy for total synthesis of the microbial metabolite (-)-bactobolin". Pure and Applied Chemistry. 61 (3): 435–438. doi: 10.1351/pac198961030435 .
Lukacs, Gabor; Ohno, Masaji (6 December 2012). Recent Progress in the Chemical Synthesis of Antibiotics. Springer Science & Business Media. p. 286. ISBN 978-3-642-75617-7.
Kocienski, Philip J. (14 May 2014). Protecting Groups, 3rd Edition 2005. Georg Thieme Verlag. p. 554. ISBN 978-3-13-179153-5.

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[Bactobolin-1] 1 2 "Bactobolin". Pubchem.ncbi.NLM.nih.gov.

[2] Greenberg, E. Peter; Chandler, Josephine R.; Seyedsayamdost, Mohammad R. (27 March 2020). "The Chemistry and Biology of Bactobolin: A 10-Year Collaboration with Natural Product Chemist Extraordinaire Jon Clardy". Journal of Natural Products. 83 (3): 738–743. doi:10.1021/acs.jnatprod.9b01237. hdl: 1808/32425 . PMC 8118907 . PMID 32105069.

[3] Weinreb, Steven M. (1995). "Total synthesis of the microbial antitumor antibiotics actinobolin and bactobolin". Studies in Natural Products Chemistry. 16: 3–25. doi:10.1016/S1572-5995(06)80051-7. ISBN 9780444822642.

[4] Munakata, Tomohiko; Ikeda, Yoshifumi; Matsuki, Hideo; Isagai, Katsuyoshi (May 1983). "Cultural Conditions and Strain Improvement for Production of Bactobolin". Agricultural and Biological Chemistry. 47 (5): 929–934. doi:10.1080/00021369.1983.10865772.

[5] Franco, Carlos M.; Belda, Beatriz Vázquez (2 December 2020). Natural Compounds as Antimicrobial Agents. MDPI. p. 134. ISBN 978-3-03936-048-2.

[6] Reinhoudt, D. N.; Connors, T. A.; Pinedo, H. M.; Poll, K. W. van de (6 December 2012). Structure-Activity Relationships of Anti-Tumour Agents. Springer Science & Business Media. p. 270. ISBN 978-94-009-6798-4.

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Names

IUPAC name (2S)-N-[(3S,4R,4aR,5R,6R)-3-(Dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-isochromen-4-yl]-2-aminopropanamide^[1]
Identifiers
CAS Number	72615-20-4 ^Y^[1]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:138579
ChEMBL	ChEMBL489472
ChemSpider	35035304
PubChem CID	54676871
UNII	EOF7S67HS2
CompTox Dashboard (EPA)	DTXSID20222944
InChI InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1 Key: RBCHRRIVFAIGFI-RGBMRXMBSA-N
SMILES C[C@@H](C(=O)N[C@@H]1[C@@H]2[C@H]([C@@H](CC(=C2C(=O)O[C@]1(C)C(Cl)Cl)O)O)O)N
Properties
Chemical formula	C₁₄H₂₀Cl₂N₂O₆
Molar mass	383.22 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

Bactobolin

References

Further reading