Chemical Formula: C18H25NO6
Chemical Formula C18H25NO6
Found 79 metabolite its formula value is C18H25NO6
Retrorsine
Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid found in certain plants. Despite its toxicity, it may have several biological functions, both in the plants that produce it and in the organisms that ingest it. Here are some possible biological functions of Retrorsine: Defense Mechanism: In plants, Retrorsine likely serves as a chemical defense against herbivores and pathogens. Its toxicity can deter animals from feeding on the plant and can inhibit the growth of microbial pathogens. Allelopathy: Retrorsine may be involved in allelopathy, which is the process by which plants release chemicals into the environment to inhibit the growth of competing plants. This can help the producing plant secure resources such as light, water, and nutrients. Insecticidal Properties: The compound may have insecticidal properties, helping to protect the plant from insect pests. Medicinal Uses: In traditional medicine, plants containing Retrorsine have been used for their supposed medicinal properties, although the use is cautioned due to the compound's toxicity. Ecological Role: Retrorsine may play a role in the ecological interactions of the plant, affecting the behavior and population dynamics of herbivores and other organisms in the ecosystem. Cell Cycle Inhibition: In biological systems, Retrorsine has been shown to inhibit cell proliferation, particularly in liver cells. This property is of interest in medical research for understanding liver toxicity and cancer. Genotoxic Effects: Retrorsine can bind to DNA, causing genotoxic effects. This can lead to mutations and has implications for cancer research. Pharmacological Research: Due to its biological activity, Retrorsine is used in pharmacological research to study the mechanisms of toxicity, carcinogenesis, and potential therapeutic targets. It's important to note that while Retrorsine has these potential biological functions, its toxicity makes it hazardous to humans and animals, and it is not used in modern medicine due to the risks associated with its ingestion. Research on Retrorsine is typically focused on understanding its mechanisms of action and toxicity to inform safety guidelines and potential therapeutic applications. Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.363 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.358 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.361 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2325 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 177 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 117 INTERNAL_ID 147; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 147 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 137 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 157 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 167 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 127 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 107 D000970 - Antineoplastic Agents Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2]. Retrorsine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=480-54-6 (retrieved 2025-03-17) (CAS RN: 480-54-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Jacobine
INTERNAL_ID 2254; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2254 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 115 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 145 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 175 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 155 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 125 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 165 INTERNAL_ID 135; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 135 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 105
Senecionine N-oxide
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2301 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 146 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 176 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 116 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 136 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 166 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 156 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 106 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 126 Senecionine n-oxide is the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Senecionine N-oxide has anti-cancer activity
Usaramine
Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\\% of biofilm formation without killing the bacteria[1]. Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\% of biofilm formation without killing the bacteria[1].
(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
Senecionine N-oxide
12-Hydroxysenecionan-11,16-dione 4-oxide
Senecionine N-oxide is a tertiary amine oxide. It is functionally related to a senecionine. Senecionine N-oxide is a natural product found in Dorobaea pimpinellifolia, Senecio gallicus, and other organisms with data available. Senecionine n-oxide is the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Senecionine N-oxide has anti-cancer activity[1][2].
Ursamine
LSM-2938 is a macrolide. Usaramine is a natural product found in Senecio malacitanus, Senecio ceratophylloides, and other organisms with data available. D000970 - Antineoplastic Agents Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\\% of biofilm formation without killing the bacteria[1]. Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\% of biofilm formation without killing the bacteria[1].
Usaramin
LSM-2938 is a macrolide. Usaramine is a natural product found in Senecio malacitanus, Senecio ceratophylloides, and other organisms with data available. D000970 - Antineoplastic Agents Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\\% of biofilm formation without killing the bacteria[1]. Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50\% of biofilm formation without killing the bacteria[1].
Senecivernine N-oxide
A pyrrolizine alkaloid that is produced by a hybrid species of Jacobaea. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2280
(+)-3alpha-(3,4,5-trimethoxybenzoyloxy)tropan-6beta-ol|3alpha-(3,4,5-Trimethoxybenzoyloxy)tropan-6beta-ol
12,13-(Xi)-ethane-1,1-diyldioxy-(13betaH,14betaH)-14,19-dihydro-20-nor-crotalanane-11,15-dione|Monocrotalinin|Monocrotalinine|O,O-(Xi)-ethane-1,1-diyl-monocrotaline
Jacobine
Jacobine is a pyrrolizine alkaloid. Jacobine is a natural product found in Crotalaria micans, Senecio brasiliensis, and other organisms with data available.
Integerrimine N-oxide
Integerrimine N-oxide is a natural product found in Senecio nebrodensis and Senecio brasiliensis with data available.
1ST40320
Retrorsine is a macrolide. Retrorsine is a natural product found in Crotalaria spartioides, Senecio malacitanus, and other organisms with data available. D000970 - Antineoplastic Agents Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2]. Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2].
1-Benzyl 5-methyl N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-glutam ate
1-Benzyl 5-methyl N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-glutam ate
(1R,4Z,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
(1R,4Z,6R,7R,14R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
(1'r,2s,3r,6'r,7'r,17'r)-7'-hydroxy-3,6',7'-trimethyl-2',9'-dioxa-14'-azaspiro[oxirane-2,4'-tricyclo[9.5.1.0¹⁴,¹⁷]heptadecan]-11'-ene-3',8'-dione
(1r,7r,11r,12r,17s)-4-ethylidene-7,12-dihydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione
(1s,4e,6s,7r,16r,17r)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(1r,4e,6r,7r,17r)-7-hydroxy-4-(2-hydroxyethylidene)-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(8r,9r,11z,14r,15s,16r)-11-ethylidene-8,15-dihydroxy-8,9-dimethyl-6,13-dioxa-1-azatricyclo[12.2.1.0⁴,¹⁶]heptadec-3-ene-7,12-dione
6-hydroxy-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.1⁵,⁸.0¹⁵,¹⁸]nonadec-12-ene-3,9-dione
(1r,4z,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,7ar)-7-({[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-4-hydroxy-3-methylbut-2-enoate
(8r,9r,11e,14r,15s)-11-ethylidene-8,15-dihydroxy-8,9-dimethyl-6,13-dioxa-1-azatricyclo[12.2.1.0⁴,¹⁶]heptadec-3-ene-7,12-dione
(1r,4e,6s,7r,17s)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
4-ethylidene-7-hydroxy-6-(hydroxymethyl)-7-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(1r,5r,7s,8s,18r)-7-hydroxy-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.1⁵,⁸.0¹⁵,¹⁸]nonadec-12-ene-3,9-dione
(1r,4e,6r,7r,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate
7-({[2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl 4-hydroxy-3-methylbut-2-enoate
(1s,4z,6r,7r)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
11-ethylidene-8,15-dihydroxy-8,9-dimethyl-6,13-dioxa-1-azatricyclo[12.2.1.0⁴,¹⁶]heptadec-3-ene-7,12-dione
(4z)-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,4z,6s,7s,17s)-4-ethylidene-7-hydroxy-6-(hydroxymethyl)-7-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(1s,4e,6s,7r,17s)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
2-methyl-4-({8-methyl-6-[(3-methylbut-2-enoyl)oxy]-8-azabicyclo[3.2.1]octan-3-yl}oxy)-4-oxobut-2-enoic acid
(1r,6r,7s,17s)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(8r,9r,11e,14r,15s,16r)-11-ethylidene-8,15-dihydroxy-8,9-dimethyl-6,13-dioxa-1-azatricyclo[12.2.1.0⁴,¹⁶]heptadec-3-ene-7,12-dione
(8r,9r,11e,14s,15r,16s)-11-ethylidene-8,15-dihydroxy-8,9-dimethyl-6,13-dioxa-1-azatricyclo[12.2.1.0⁴,¹⁶]heptadec-3-ene-7,12-dione
(1r,5s,6r,7r,8s,18r)-6-hydroxy-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.1⁵,⁸.0¹⁵,¹⁸]nonadec-12-ene-3,9-dione
(1r,6r,7s)-4-ethylidene-7-hydroxy-6,14-dimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
(1r,4e,6r,7r,14r,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate
7-({[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2e)-4-hydroxy-3-methylbut-2-enoate
(1r,4e,6r,7r,17s)-4-ethylidene-7-hydroxy-6-(hydroxymethyl)-7-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(1r,4z,6s,7r,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
4-ethylidene-7,12-dihydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione
(1s,4e,6r,7r,16r,17r)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(2e)-2-methyl-4-{[(1r,3r,5s,6r)-8-methyl-6-[(3-methylbut-2-enoyl)oxy]-8-azabicyclo[3.2.1]octan-3-yl]oxy}-4-oxobut-2-enoic acid
(1r,4z,6r,7s,16s,17s)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
7-hydroxy-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.1⁵,⁸.0¹⁵,¹⁸]nonadec-12-ene-3,9-dione
(1r,4z,7r,11r,12r,17s)-4-ethylidene-7,12-dihydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione
(1s,4z,6r,7r,16s,17r)-4-ethylidene-7,16-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
(1r,4z,6r,7s,11z)-4-ethylidene-7-hydroxy-6,14-dimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
4-Ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
4-Ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione has been reported in Packera glabella with data available.
