Classification Term: 2058

Anthracyclines (ontology term: CHEMONTID:0002106)

Polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage." []

found 43 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Phenylpropanoids and polyketides

Child Taxonomies: There is no child term of current ontology term.

Daunorubicin

(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H29NO10 (527.1791374000001)

Daunorubicin is only found in individuals that have used or taken this drug. It is a very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01D - Cytotoxic antibiotics and related substances > L01DB - Anthracyclines and related substances C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent D004791 - Enzyme Inhibitors KEIO_ID D106

Epirubicin

(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H29NO11 (543.1740524)

Epirubicin is only found in individuals that have used or taken this drug. It is an anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. [PubChem]Epirubicin has antimitotic and cytotoxic activity. It inhibits nucleic acid (DNA and RNA) and protein synthesis through a number of proposed mechanisms of action: Epirubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It also interferes with DNA replication and transcription by inhibiting DNA helicase activity. L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01D - Cytotoxic antibiotics and related substances > L01DB - Anthracyclines and related substances C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent D004791 - Enzyme Inhibitors Same as: D07901

Doxorubicinol

(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H31NO11 (545.1897016)

Doxorubicinol belongs to the family of Anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Valrubicin

2,2,2-Trifluoro-N-(3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl)ethanimidate

C34H36F3NO13 (723.2138642)

Valrubicin is only found in individuals that have used or taken this drug. It is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. [Wikipedia]Valrubicin is an anthracycline that affects a variety of inter-related biological functions, most of which involve nucleic acid metabolism. It readily penetrates into cells, where after DNA intercalation, it inhibits the incorporation of nucleosides into nucleic acids, causes extensive chromosomal damage, and arrests cell cycle in G2. Although valrubicin does not bind strongly to DNA, a principal mechanism of its action, mediated by valrubicin metabolites, is interference with the normal DNA breaking-resealing action of DNA topoisomerase II.

N-Trifluoroacetyladriamycinol

N-(6-{[3-(1,2-dihydroxyethyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl)-2,2,2-trifluoroethanimidic acid

C29H30F3NO12 (641.1720016)

N-Trifluoroacetyladriamycinol is a metabolite of valrubicin. Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. It was originally launched as Valstar in the U.S. (Wikipedia)

N-Trifluoroacetyladriamycin

2,2,2-trifluoro-N-[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl]acetamide

C29H28F3NO12 (639.1563524000001)

N-Trifluoroacetyladriamycin is a metabolite of valrubicin. Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. It was originally launched as Valstar in the U.S. (Wikipedia)

9-Ethyl-4,6,9,10,11-pentahydroxy-7-[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-8,10-dihydro-7H-tetracene-5,12-dione

C30H35NO11 (585.221)

11-Hydroxyaclacinomycin X

Methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid

C42H52N2O16 (840.3316672000001)

13-Dihydrodaunorubicin

10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H31NO10 (529.1947866)

2-Pyrrolino-dox

10-{[4-(2,3-dihydro-1H-pyrrol-1-yl)-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C31H33NO11 (595.2053508)

3'-Deamino-3'-(2-methoxy-4-morpholinyl)doxorubicin

6,8-dihydroxy-10-{[5-hydroxy-4-(2-methoxymorpholin-4-yl)-6-methyloxan-2-yl]oxy}-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C32H37NO12 (627.2315642000001)

5,12-Naphthacenedione, 10-((4-aminotetrahydro-6-methyl-2H-pyran-2-yl)oxy)-8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-

C27H31NO10 (529.1947866)

Aclacinomycin A zwitterion

Methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxooxan-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid

C42H53NO15 (811.3415028)

Aclacinomycin B

methyl 4-{[5-({5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-12-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

C42H51NO15 (809.3258536)

D000970 - Antineoplastic Agents D007155 - Immunologic Factors

aclacinomycin S

4-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-(dimethylazaniumyl)-6-methyloxan-2-yl}oxy)-2-ethyl-2,7-dihydroxy-1-(methoxycarbonyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-olate

C36H45NO13 (699.289076)

Aclacinomycin X

Methyl 4-{[5-({5-[(3-amino-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid

C42H52N2O15 (824.3367522000001)

D000970 - Antineoplastic Agents D007155 - Immunologic Factors

Aclacinomycin Y

methyl 4-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

C42H51NO15 (809.3258536)

D000970 - Antineoplastic Agents D007155 - Immunologic Factors

Aklavin

Methyl 4-{[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid

C30H35NO10 (569.226085)

Aldoxorubicin

N-(1-{4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl}-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazonate

C37H42N4O13 (750.2748242)

Annamycin

7-[(4,5-dihydroxy-3-iodo-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C26H25IO11 (640.0441569999999)

beta-Isorhodomycinone

10-{[4-(dimethylamino)-5-({4-hydroxy-6-methyl-5-[(6-methyl-5-oxooxan-2-yl)oxy]oxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-8-ethyl-1,4,6,7,8,11-hexahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C40H51NO16 (801.3207686)

Carminomycin I

8-acetyl-10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,6,8,11-tetrahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C26H27NO10 (513.1634882000001)

D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors D004791 - Enzyme Inhibitors

Dox-ga3

3,4,5-Trihydroxy-6-({[4-({[(3-hydroxy-2-methyl-6-{[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl)-C-hydroxycarbonimidoyl]oxy}methyl)phenyl]carbamoyl}oxy)oxane-2-carboxylate

C41H42N2O20 (882.2330812)

Epirubicin glucuronide

6-[(4-amino-2-methyl-6-{[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C33H37NO17 (719.2061392)

Esorubicin

10-[(4-amino-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H29NO10 (527.1791374000001)

D000970 - Antineoplastic Agents

Galarubicin

2-{4-[(3-fluoro-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl}-2-oxoethyl 3-aminopropanoic acid

C30H32FNO13 (633.1857594)

Hydroxyrubicin

10-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C27H28O12 (544.1580688)

Idarubicinol

7-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(1-hydroxyethyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

C26H29NO9 (499.18422240000007)

(9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

C26H27NO9 (497.1685732000001)

D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors D004791 - Enzyme Inhibitors