Resistomycin

Resistomycin
Names
	IUPAC name 6,10,14,19-Tetrahydroxy-4,9,9-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(19),3,5,7,10,13,15,17-octaene-2,12-dione
	Other names Heliomycin; Geliomycin; Itamycin; 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-2H-Benzo[cf]pyrene-2,6(1H)-dione; 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-2H-Benzo[cd]pyrene-2,6(1H)-dione; 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-2H-benzo[cf]pyrene-2,6(1H)-dione; 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-1H-benzo[cd]pyrene-2,6-dione; ;
Identifiers
CAS Number	20004-62-0 ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:29671 ;
ChEMBL	ChEMBL1320139 ;
ChemSpider	78436128 ;
KEGG	C12080 ;
PubChem CID	135430323 ;
UNII	7N3A092A5X ;
CompTox Dashboard (EPA)	DTXSID4046101 ;
	InChI InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,24-25,27-28H,1-3H3 Key: MJKDGCARCYPVQG-UHFFFAOYSA-N;
	SMILES CC1(C)C2=C3C=4C(C(=O)C=5C3=C(C(O)=C2)C(C)=CC5O)=C(O)C=C(O)C4C1=O;
Properties
Chemical formula	C22H16O6
Molar mass	376.364 g·mol−1
Boiling point	315°C
	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 09, 2025

Resistomycin is an antibiotic with the molecular formula C₂₂H₁₆O₆.^[3]^[1]^[4] Resistomycin is similar to hypericin.^[5] Resistomycin was first isolated in 1951 from the bacterium Streptomyces resistomycificus .^[6]

References

1 2 "Resistomycin". Pubchem.ncbi.NLM.nih.gov.
↑ Fugmann, Burkhard (14 May 2014). RÖMPP Lexikon Naturstoffe, 1. Auflage, 1997 (in German). Georg Thieme Verlag. p. 545. ISBN 978-3-13-179291-4.
↑ Brockmann, Hans; Schmidt-Kastner, Günter (1951). "Resistomycin, ein neues Antibioticum aus Actinomyceten". Die Naturwissenschaften. 38 (20): 479–480. Bibcode:1951NW.....38..479B. doi:10.1007/BF00622090. S2CID 33750932.
↑ Ho, Tse-Lok (1996). Evolution of Synthetic Pathways: Parallax and Calibration. World Scientific. p. 301. ISBN 978-981-02-2669-5.
↑ Shiono, Yoshihito; Shiono, Nobuyo; Seo, Shujiro; Oka, Syuichi; Yamazaki, Yoshimitsu (1 October 2002). "Effects of Polyphenolic Anthrone Derivatives, Resistomycin and Hypericin, on Apoptosis in Human Megakaryoblastic Leukemia CMK-7 Cell Line". Zeitschrift für Naturforschung C. 57 (9–10): 923–929. doi: 10.1515/znc-2002-9-1028 . PMID 12440735. S2CID 9120617.
↑ Korzybski, Tadeusz; Kowszyk-Gindifer, Zuzanna; Kurylowicz, Wlodzimierz (3 September 2013). Antibiotics: Origin, Nature and Properties. Elsevier. p. 289. ISBN 978-1-4832-2305-6.

Brockmann, Hans; Meyer, Ernst; Schrempp, Klaus; Reiners, Fritz; Reschke, Till (April 1969). "Resistomycin, IV. Die Konstitution des Resistomycins". Chemische Berichte. 102 (4): 1224–1246. doi:10.1002/cber.19691020415. PMID 5802095.
Comprehensive Natural Products II: Chemistry and Biology. Elsevier. 5 March 2010. p. 266. ISBN 978-0-08-045382-8.

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

[2] Fugmann, Burkhard (14 May 2014). RÖMPP Lexikon Naturstoffe, 1. Auflage, 1997 (in German). Georg Thieme Verlag. p. 545. ISBN 978-3-13-179291-4.

[3] Brockmann, Hans; Schmidt-Kastner, Günter (1951). "Resistomycin, ein neues Antibioticum aus Actinomyceten". Die Naturwissenschaften. 38 (20): 479–480. Bibcode:1951NW.....38..479B. doi:10.1007/BF00622090. S2CID 33750932.

[4] Ho, Tse-Lok (1996). Evolution of Synthetic Pathways: Parallax and Calibration. World Scientific. p. 301. ISBN 978-981-02-2669-5.

[5] Shiono, Yoshihito; Shiono, Nobuyo; Seo, Shujiro; Oka, Syuichi; Yamazaki, Yoshimitsu (1 October 2002). "Effects of Polyphenolic Anthrone Derivatives, Resistomycin and Hypericin, on Apoptosis in Human Megakaryoblastic Leukemia CMK-7 Cell Line". Zeitschrift für Naturforschung C. 57 (9–10): 923–929. doi: 10.1515/znc-2002-9-1028 . PMID 12440735. S2CID 9120617.

[6] Korzybski, Tadeusz; Kowszyk-Gindifer, Zuzanna; Kurylowicz, Wlodzimierz (3 September 2013). Antibiotics: Origin, Nature and Properties. Elsevier. p. 289. ISBN 978-1-4832-2305-6.

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Names

IUPAC name 6,10,14,19-Tetrahydroxy-4,9,9-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(19),3,5,7,10,13,15,17-octaene-2,12-dione^[1]
Other names Heliomycin Geliomycin Itamycin 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-2H-Benzo[cf]pyrene-2,6(1H)-dione 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-2H-Benzo[cd]pyrene-2,6(1H)-dione 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-2H-benzo[cf]pyrene-2,6(1H)-dione 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-1H-benzo[cd]pyrene-2,6-dione
Identifiers
CAS Number	20004-62-0 ^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29671
ChEMBL	ChEMBL1320139
ChemSpider	78436128
KEGG	C12080
PubChem CID	135430323
UNII	7N3A092A5X
CompTox Dashboard (EPA)	DTXSID4046101
InChI InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,24-25,27-28H,1-3H3 Key: MJKDGCARCYPVQG-UHFFFAOYSA-N
SMILES CC1(C)C2=C3C=4C(C(=O)C=5C3=C(C(O)=C2)C(C)=CC5O)=C(O)C=C(O)C4C1=O
Properties
Chemical formula	C₂₂H₁₆O₆
Molar mass	376.364 g·mol⁻¹
Boiling point	315°C^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Resistomycin

References

Further reading