Sibiromycin

Sibiromycin
Names
	IUPAC name (6R,6aS)-2-[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-4,6-dihydroxy-3-methyl-8-[(E)-prop-1-enyl]-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
	Other names Sybiromycin
Identifiers
CAS Number	12684-33-2 ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:90941 ;
ChEMBL	ChEMBL462584 ;
ChemSpider	4941925 ;
PubChem CID	6437361 ;
CompTox Dashboard (EPA)	DTXSID101318295 ;
	InChI InChI=1S/C24H33N3O7/c1-6-7-13-8-15-21(30)26-17-14(22(31)27(15)10-13)9-16(11(2)18(17)28)34-23-20(29)24(4,32)19(25-5)12(3)33-23/h6-7,9-10,12,15,19-21,23,25-26,28-30,32H,8H2,1-5H3/b7-6+/t12-,15-,19-,20-,21+,23-,24+/m0/s1 Key: RAGFPHFDFVNLCG-INYQBOQCSA-N;
	SMILES C/C=C/C1=CN2[C@@H](C1)[C@H](NC3=C(C(=C(C=C3C2=O)O[C@H]4[C@@H]([C@]([C@H]([C@@H](O4)C)NC)(C)O)O)C)O)O;
Properties
Chemical formula	C24H33N3O7
Molar mass	475.542 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 July 12, 2025

Sibiromycin is an antitumor antibiotic with the molecular formula C₂₄H₃₃N₃O₇ which is produced by the bacterium Streptosporangium sibiricum .^[1]^[2]^[3]^[4] Sibiromycin is a pyrrolobenzodiazepine.^[5]^[6]

References

1 2 3 "Sibiromycin". Pubchem.ncbi.NLM.nih.gov.
↑ Gause, G. F. (1975). "Sibiromycin". Mechanism of Action of Antimicrobial and Antitumor Agents. pp. 269–273. doi:10.1007/978-3-642-46304-4_17. ISBN 978-3-642-46306-8.
↑ Li, Wei; Khullar, Ankush; Chou, ShenChieh; Sacramo, Ashley; Gerratana, Barbara (May 2009). "Biosynthesis of Sibiromycin, a Potent Antitumor Antibiotic". Applied and Environmental Microbiology. 75 (9): 2869–2878. Bibcode:2009ApEnM..75.2869L. doi:10.1128/AEM.02326-08. PMC 2681668 . PMID 19270142.
↑ Rhoads, Robert E. (6 December 2012). Proceedings of the Research Symposium on Complexes of Biologically Active Substances with Nucleic Acids and Their Modes of Action: Held at the Walter Reed Army Institute of Research Washington, 16–19 March 1970. Springer Science & Business Media. p. 33. ISBN 978-3-642-65141-0.
↑ Antibiotics and Chemotherapy. S. Karger. 1980. p. 105. ISBN 978-3-8055-2830-6.
↑ Rahman, Khondaker Miraz; Thurston, David E. (6 September 2018). Small-Molecule Transcription Factor Inhibitors in Oncology. Royal Society of Chemistry. p. 87. ISBN 978-1-78262-145-4.

Kersten, H.; Kersten, W. (11 November 2013). Inhibitors of Nucleic Acid Synthesis: Biophysical and Biochemical Aspects. Springer Science & Business Media. p. 19. ISBN 978-3-642-80855-5.
Corcoran, John W. (6 December 2012). Biosynthesis. Springer Science & Business Media. p. 277. ISBN 978-3-642-67724-3.
Comprehensive Natural Products III. Elsevier. 22 July 2020. p. 412. ISBN 978-0-08-102691-5.

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[Sibiromycin-1] 1 2 3 "Sibiromycin". Pubchem.ncbi.NLM.nih.gov.

[2] Gause, G. F. (1975). "Sibiromycin". Mechanism of Action of Antimicrobial and Antitumor Agents. pp. 269–273. doi:10.1007/978-3-642-46304-4_17. ISBN 978-3-642-46306-8.

[3] Li, Wei; Khullar, Ankush; Chou, ShenChieh; Sacramo, Ashley; Gerratana, Barbara (May 2009). "Biosynthesis of Sibiromycin, a Potent Antitumor Antibiotic". Applied and Environmental Microbiology. 75 (9): 2869–2878. Bibcode:2009ApEnM..75.2869L. doi:10.1128/AEM.02326-08. PMC 2681668 . PMID 19270142.

[4] Rhoads, Robert E. (6 December 2012). Proceedings of the Research Symposium on Complexes of Biologically Active Substances with Nucleic Acids and Their Modes of Action: Held at the Walter Reed Army Institute of Research Washington, 16–19 March 1970. Springer Science & Business Media. p. 33. ISBN 978-3-642-65141-0.

[5] Antibiotics and Chemotherapy. S. Karger. 1980. p. 105. ISBN 978-3-8055-2830-6.

[6] Rahman, Khondaker Miraz; Thurston, David E. (6 September 2018). Small-Molecule Transcription Factor Inhibitors in Oncology. Royal Society of Chemistry. p. 87. ISBN 978-1-78262-145-4.

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Names

IUPAC name (6R,6aS)-2-[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-4,6-dihydroxy-3-methyl-8-[(E)-prop-1-enyl]-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one^[1]
Other names Sybiromycin^[1]
Identifiers
CAS Number	12684-33-2 ^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:90941
ChEMBL	ChEMBL462584
ChemSpider	4941925
PubChem CID	6437361
CompTox Dashboard (EPA)	DTXSID101318295
InChI InChI=1S/C24H33N3O7/c1-6-7-13-8-15-21(30)26-17-14(22(31)27(15)10-13)9-16(11(2)18(17)28)34-23-20(29)24(4,32)19(25-5)12(3)33-23/h6-7,9-10,12,15,19-21,23,25-26,28-30,32H,8H2,1-5H3/b7-6+/t12-,15-,19-,20-,21+,23-,24+/m0/s1 Key: RAGFPHFDFVNLCG-INYQBOQCSA-N
SMILES C/C=C/C1=CN2[C@@H](C1)[C@H](NC3=C(C(=C(C=C3C2=O)O[C@H]4[C@@H]([C@]([C@H]([C@@H](O4)C)NC)(C)O)O)C)O)O
Properties
Chemical formula	C₂₄H₃₃N₃O₇
Molar mass	475.542 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

Sibiromycin

References

Further reading