Classification Term: 1894

Macrolides and analogues (ontology term: CHEMONTID:0000147)

Organic compounds containing a lactone ring of at least twelve members." []

found 49 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Phenylpropanoids and polyketides

Child Taxonomies: Epothilones and analogues, Zearalenones, Pectenotoxins and derivatives, Milbemycins

Zeranol

7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one

C18H26O5 (322.1780146)


Zeranol is isolated from Fusarium species. It is an anabolic agent and estrogenic agent (mainly veterinary use). Zeranol is used as a growth promoter for food animals. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. It may also arise in livestock by ingestion of Fusarium contaminated pasture or feeds D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Same as: D06362

   

alpha-Zearalenol

(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one

C18H24O5 (320.1623654)


Alpha-zearlenol is a nonsteroidal estrogen or mycoestrogen found in fungi belonging to the Fusarium genus including F. graminearum, F. culmorum, F. crookwellense, etc (PMID: 22095651), As a mycotoxin, alpha-zearalenol is a widely distributed compound that contaminates many crops, grains, and other commodities (PMID: 30830360). Alpha-zearalenol, is also a major hepatic metabolite of zearalenone (another mycotoxin). Zearalenone has two metabolites, alpha and beta zearalenol which are produced in the liver by 3α-hydroxisteroid dehydrogenase and 3β-hydroxisteroid dehydrogenase (PMID: 30830360). Like Alpha-zearlenol, zearalenone or F-2 mycotoxin is produced by certain Fusarium species. It causes infertility, abortion and other breeding problems in swine. Alpha-zearlenol is also produced synthetically and sold as Zeranol, which is used as an anabolic agent for cattle. Alpha-zearlenol exhibits strong growth-promoting properties, but its sale is restricted in Europe (PMID: 22095651). Alpha-zearalenol has three to four times the biological activity of zearalenone. Alpha-zearlenol contains a lactone ring in its structure and is structurally analogous to estrogen, thus it can bind to estrogen receptors, and causes hepatotoxic, hematotoxic, immunotoxic, genotoxic, teratogenic and carcinogenic effects on different animal species (PMID: 17045381).

   

Carpaine

13,26-dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.2¹¹,¹⁴]triacontane-3,16-dione

C28H50N2O4 (478.377038)


Pseudocarpaine is found in fruits. Minor alkaloid from leaves of Carica papaya (papaya Alkaloid from leaves of Carica papaya (papaya)

   

Fluvalinate

cyano(3-phenoxyphenyl)methyl 2-{[2-chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoate

C26H22ClF3N2O3 (502.1270968)


D010575 - Pesticides > D007306 - Insecticides > D011722 - Pyrethrins D016573 - Agrochemicals

   

beta-Zearalenol

(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one

C18H24O5 (320.1623654)


Beta-zearalenol is a nonsteroidal estrogen or mycoestrogen found in fungi belonging to the Fusarium genus including F. graminearum, F. culmorum, F. crookwellense, etc (PMID: 22095651), As a mycotoxin, beta-zearalenol is a widely distributed compound that contaminates many crops, grains, and other commodities (PMID: 30830360). Beta-zearalenol is the beta epimer of alpha-zearalenol. It is also a major hepatic metabolite of zearalenone (another mycotoxin). Zearalenone has two major metabolites, alpha and beta zearalenol which are produced in the liver by 3α-hydroxisteroid dehydrogenase and 3β-hydroxisteroid dehydrogenase (PMID: 30830360). Beta-zearalenol is formed mainly in the liver but also to a lesser extent in the intestines during first-pass metabolism. It contains a lactone ring in its structure and is structurally analogous to estrogen, thus it can bind to estrogen receptors, and causes hepatotoxic, hematotoxic, immunotoxic, genotoxic, teratogenic and carcinogenic effects on different animal species (PMID: 17045381). However, beta-zearalenol is somewhat less active estrogenically than alpha-zearalenol. β-Zearalenol is a non-steroidal estrogenic mycotoxin synthesized by Fusarium species. β-Zearalenol potentially influences transcription and effects gene expression on translational level[1].

   

Exaltolide

Pentadecanoic acid, 15-hydroxy-, laquo Xiraquo -lactone

C15H28O2 (240.20891880000002)


Cyclopentadecanolide is a macrolide. Oxacyclohexadecan-2-one is a natural product found in Lonicera japonica and Angelica archangelica with data available. Constituent of angelica root oil (Angelica archangelica). Flavouring agent. Exaltolide is found in fats and oils, herbs and spices, and green vegetables. Exaltolide is found in fats and oils. Exaltolide is a constituent of angelica root oil (Angelica archangelica). Exaltolide is a flavouring agent ω-Pentadecalactone is a fragrance ingredient. ω-Pentadecalactone is a member of the fragrance structural group macrocyclic lactone and lactide derivative[1]. ω-Pentadecalactone is a fragrance ingredient. ω-Pentadecalactone is a member of the fragrance structural group macrocyclic lactone and lactide derivative[1].

   

(Z)-7-Hexadecen-1,16-olide

16-Hydroxy-7-hexadecenoic acid lactone

C16H28O2 (252.20891880000002)


Once used in fruit flavouring; its use has been discontinued due to its toxic natur

   

Oxacyclotetradecan-2-one

Tridecanoic acid, 13-hydroxy-, laquo muraquo -lactone

C13H24O2 (212.1776204)


Constituent of blackberries (Rubus species) and Angelica archangelica (angelica). Oxacyclotetradecan-2-one is found in fats and oils, fruits, and green vegetables. Oxacyclotetradecan-2-one is found in fats and oils. Oxacyclotetradecan-2-one is a constituent of blackberries (Rubus sp.) and Angelica archangelica (angelica).

   

Protoisoeruboside B

2-({2-[(6-{[6,19-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C57H96O30 (1260.5986116)


Protoisoeruboside B is found in onion-family vegetables. Protoisoeruboside B is a constituent of fresh garlic bulbs (Allium sativum)

   

Yuzu lactone

(10E)-1-oxacyclotridec-10-en-2-one

C12H20O2 (196.14632200000003)


Yuzu lactone is found in citrus. Yuzu lactone is a constituent of Citrus junos (yuzu). Constituent of Citrus junos (yuzu). Yuzu lactone is found in citrus.

   

(R)-14-Methyloxacyclotetradecan-2-one

(R)-14-Methyloxacyclotetradecan-2-one

C14H26O2 (226.1932696)


(R)-14-Methyloxacyclotetradecan-2-one is found in herbs and spices. (R)-14-Methyloxacyclotetradecan-2-one is a constituent of Ferula galbaniflua (galbanum)

   

10-Oxo-11-octadecen-13-olide

(12E)-14-pentyl-1-oxacyclotetradec-12-ene-2,11-dione

C18H30O3 (294.21948299999997)


10-Oxo-11-octadecen-13-olide is found in cereals and cereal products. 10-Oxo-11-octadecen-13-olide is isolated from cor

   

Lagerstroemine

9-hydroxy-5,6-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.1⁸,¹².0²,⁷.0¹⁹,²⁴]hexacosa-2,4,6,8,10,12(26)-hexaen-15-one

C26H31NO5 (437.2202116)


Lagerstroemine is found in fruits. Lagerstroemine is an alkaloid from Plantago psyllium seeds (African plantain

   

12-Methyl-13-tridecanolide

13-methyl-1-oxacyclotetradecan-2-one

C14H26O2 (226.1932696)


12-Methyl-13-tridecanolide is found in fats and oils. 12-Methyl-13-tridecanolide is a constituent of root of Angelica archangelica (angelica)

   

Dehydrocarpaine I

13,26-dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.2¹¹,¹⁴]triacont-12-ene-3,16-dione

C28H48N2O4 (476.3613888)


Dehydrocarpaine I is found in fruits. Dehydrocarpaine I is an alkaloid from the leaves of Carica papaya (papaya Alkaloid from the leaves of Carica papaya (papaya). Dehydrocarpaine I is found in papaya and fruits.

   

15-Hexadecanolide

16-Methyloxacyclohexadecan-2-one, 9ci

C16H30O2 (254.224568)


15-Hexadecanolide is found in herbs and spices. 15-Hexadecanolide is a constituent of Galbanum absolute (from Ferula galbaniflua and Ferula rubicaulis)

   

Isoambrettolide

9-Hexadecenoic acid, 16-hydroxy-, O-lactone (7ci)

C16H28O2 (252.20891880000002)


Isoambrettolide is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")

   

D6-Ambrettolide

(7E)-1-oxacycloheptadec-7-en-2-one

C16H28O2 (252.20891880000002)


D6-Ambrettolide is a flavouring ingredient. Flavouring ingredient

   

Ethylene brassylate

Tridecanedioic acid, cyclic ethylene ester

C15H26O4 (270.1830996)


Ethylene brassylate is a component of fragrances for soaps, detergents, food etc. Component of fragrances for soaps, detergents, food etc.

   

Amifloxacin

6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

C16H19FN4O3 (334.1441116)


Amifloxacin belongs to the family of Phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D024841 - Fluoroquinolones C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic D004791 - Enzyme Inhibitors

   

(17E,19E,21E,23E,25E)-4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

(17E,19E,21E,23E,25E)-4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

C35H58O11 (654.3978918)


   

(1R,4E,5'R,6R,6'R,7S,8S,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,29S)-22-Ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,29-octamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione

(1R,4E,5R,6R,6R,7S,8S,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,29S)-22-Ethyl-7,11,14,15-tetrahydroxy-6-(2-hydroxypropyl)-5,6,8,10,12,14,16,29-octamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2-oxane]-3,9,13-trione

C44H72O11 (776.5074362)


   

(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

C18H25NO6 (351.168179)


   

(1R,7S,13S,15S)-2,15-Dihydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one

1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one

C16H24O4 (280.1674504)


   

Avermectin A1a

6-(butan-2-yl)-24-hydroxy-12-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-21-methoxy-5,11,13,22-tetramethyl-5,6-dihydro-3,7,19-trioxaspiro[pyran-2,6-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10,14,16,22-tetraen-2-one

C49H74O14 (886.5078304)


   

Doramectin

6-cyclohexyl-21,24-dihydroxy-12-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11,13,22-tetramethyl-5,6-dihydro-3,7,19-trioxaspiro[pyran-2,6-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10,14,16,22-tetraen-2-one

C50H74O14 (898.5078304)


   

Integerrimine

4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

C18H25NO5 (335.173264)


   

(4S,8R)-8,16,18-Trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one

(4S,8R)-8,16,18-Trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one

C18H24O5 (320.1623654)


   

7-O-Succinyl macrolactin A

4-[(14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl)oxy]-4-oxobutanoic acid

C28H38O8 (502.2566548)


   

Bafilomycin A1(Baf-A1)

16-{4-[2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl}-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one

C35H58O9 (622.4080618)


   

Aab(1) avermectin

N-[6-({6-[6-(butan-2-yl)-21,24-dihydroxy-5,11,13,22-tetramethyl-5,6-dihydro-3,7,19-trioxaspiro[pyran-2,6-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10,14,16,22-tetraen-2-oneoxy]-4-methoxy-2-methyloxan-3-yl}oxy)-4-methoxy-2-methyloxan-3-yl]acetamide

C50H75NO14 (913.518729)


   

Alongside

4-hydroxy-12-methyl-1-oxacyclododeca-5,9-diene-2,8-dione

C12H16O4 (224.10485359999998)


   

Avermectin

6-(butan-2-yl)-21,24-dihydroxy-12-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11,13,22-tetramethyl-5,6-dihydro-3,7,19-trioxaspiro[pyran-2,6-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10,14,16,22-tetraen-2-one

C48H72O14 (872.4921812)


   

Concanamycin

18-{4-[2,4-dihydroxy-5-methyl-6-(prop-1-en-1-yl)oxan-2-yl]-3-hydroxypentan-2-yl}-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one

C39H64O10 (692.4499244)


   

concanamycin a

{[6-({2-[4-(11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl)-3-hydroxypentan-2-yl]-2-hydroxy-5-methyl-6-(prop-1-en-1-yl)oxan-4-yl}oxy)-4-hydroxy-2-methyloxan-3-yl]oxy}methanimidate

C46H75NO14 (865.518729)


   

Fidaxomicin

6-{[12-({3,4-dihydroxy-6,6-dimethyl-5-[(2-methylpropanoyl)oxy]oxan-2-yl}oxy)-11-ethyl-8-hydroxy-18-(1-hydroxyethyl)-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoic acid

C52H74Cl2O18 (1056.4251964)


   

Filipin II

3-hexyl-4,6,8,10,12,14,16,27-octahydroxy-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

C35H58O10 (638.4029768)


   

latrunculin a

4-{17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl}-1,3-thiazolidin-2-one

C22H31NO5S (421.19228360000005)


   

latrunculin B

4-{15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl}-1,3-thiazolidin-2-one

C20H29NO5S (395.17663440000007)


   

lipiarmycin a4

6-{[12-({3,4-dihydroxy-6,6-dimethyl-5-[(2-methylpropanoyl)oxy]oxan-2-yl}oxy)-11-ethyl-8-hydroxy-18-(1-hydroxyethyl)-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2,4-dihydroxy-6-methylbenzoate

C51H72Cl2O18 (1042.4095472000001)


   

Macrolactin-A

8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

C24H34O5 (402.24061140000003)


   

Avemectin B1

6-(butan-2-yl)-22,25-dihydroxy-12-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11,13,23-tetramethyl-5,6-dihydro-3,7,19-trioxaspiro[pyran-2,6-tetracyclo[15.7.1.1^{4,8}.0^{21,25}]hexacosane]-10,14,16,23-tetraen-2-one

C49H74O14 (886.5078304)


   

Nonactin

2,5,11,14,20,23,29,32-octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.1⁷,¹⁰.1¹⁶,¹⁹.1²⁵,²⁸]tetracontane-3,12,21,30-tetrone

C40H64O12 (736.4397544)


   

Oligomycin

22-ethyl-7,11,14,15-tetrahydroxy-6-(2-hydroxypropyl)-5,6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2-oxane]-4,18,20-triene-3,9,13-trione

C45H74O11 (790.5230854)


   

Sagopilone

7,11-dihydroxy-8,8,12,16-tetramethyl-3-(2-methyl-1,3-benzothiazol-5-yl)-10-(prop-2-en-1-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

C30H41NO6S (543.2654446)


   

Ornithylamphotericin methyl ester

2,5-Diamino-N-(3,5-dihydroxy-2-methyl-6-{[1,3,5,6,9,11,17,37-octahydroxy-36-(methoxycarbonyl)-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaen-33-yl]oxy}oxan-4-yl)pentanimidate

C53H85N3O18 (1051.582783)


   

Tiacumicin C

6-{[12-({4,5-dihydroxy-6,6-dimethyl-3-[(2-methylpropanoyl)oxy]oxan-2-yl}oxy)-11-ethyl-8-hydroxy-18-(1-hydroxyethyl)-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoic acid

C52H74Cl2O18 (1056.4251964)


   

PL

(11E,13E)-6-[(4-acetyl-3,4-dihydroxy-6-methyloxan-2-yl)oxy]-7-ethyl-4,10-dihydroxy-5-methoxy-9,16-dimethyl-1-oxacyclohexadeca-11,13-dien-2-one

C28H46O10 (542.3090816)


Pl, also known as ddaxhpp-ii, is a member of the class of compounds known as macrolides and analogues. Macrolides and analogues are organic compounds containing a lactone ring of at least twelve members. Pl is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pl can be found in cucumber, which makes pl a potential biomarker for the consumption of this food product. PL, P.L., Pl, or .pl may refer to: .

   

11-Oxahexadecanolide

1,7-dioxacycloheptadecan-8-one

C15H28O3 (256.2038338)


Flavouring compound [Superscent]