NCBI Taxonomy: 205481

Pachyrhizus tuberosus (ncbi_taxid: 205481)

found 26 associated metabolites at species taxonomy rank level.

Ancestor: Pachyrhizus

Child Taxonomies: none taxonomy data.

Rotenone

[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2alpha,6aalpha,12aalpha)]-

C23H22O6 (394.1416)


Rotenone appears as colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste. (NTP, 1992) Rotenone is a member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). It has a role as a phytogenic insecticide, a mitochondrial NADH:ubiquinone reductase inhibitor, a metabolite, an antineoplastic agent, a toxin and a piscicide. It is an organic heteropentacyclic compound and a member of rotenones. Rotenone is an isoflavone compound that naturally occurs in the jicama vine plant as well as many Fabaceae plants. It has broad spectrum insecticide and pesticide activity and is also toxic to fish. Rotenone is a natural product found in Pachyrhizus erosus, Millettia ferruginea, and other organisms with data available. Rotenone is a naturally occurring organic heteropentacyclic compound and member of rotenones that is found in the roots of several plant species. It is a mitochondrial NADH:ubiquinone reductase inhibitor, toxin, and metabolite, and is used as an antineoplastic agent and insecticide. It is characterized as a colorless to brownish or a white to brownish-white crystalline solid that is odorless. Exposure occurs by inhalation, ingestion, or contact. Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinsons disease. (Wikipedia) Rotenone has been shown to exhibit apoptotic, neuroprotectant and neuroprotective functions (A7776, A7777, A7777).Rotenone belongs to the family of Rotenoids. These are phenolic compounds containing aA cis-fused tetrahydrochromeno[3,4-b]chromenenucleus. Many rotenoids contain an additional ring, e.g rotenone[1]. (Reference: [1] IUPAC. Compendium of Chemical Terminology, 2nd ed. (the Gold Book). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. (PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1364)). A botanical insecticide that is an inhibitor of mitochondrial electron transport. Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinsons disease. A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). Widely distrib. in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean) D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production.

   

Pachyrrhizin

6-(6-Methoxy-1,3-benzodioxol-5-yl)-7H-furo[3,2-g][1]benzopyran-7-one, 9ci

C19H12O6 (336.0634)


Pachyrrhizin is found in jicama. Pachyrrhizin is a constituent of Pachyrrhizus erosus (yam bean). Constituent of Pachyrrhizus erosus (yam bean). Pachyrrhizin is found in jicama and pulses.

   

13alpha-Hydroxydolineone

1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O7 (352.0583)


13alpha-Hydroxydolineone is found in jicama. 13alpha-Hydroxydolineone is a constituent of Pachyrrhizus erosus (yam bean) Constituent of Pachyrrhizus erosus (yam bean). 13alpha-Hydroxydolineone is found in jicama and pulses.

   

Dolineone

5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O6 (336.0634)


Dolineone is found in jicama. Dolineone is isolated from roots of Pachyrrhizus erosus (yam bean). Isolated from roots of Pachyrrhizus erosus (yam bean). Dolineone is found in jicama and pulses.

   

Erosone

Isoelliptone

C20H16O6 (352.0947)


   

Neotenone

6,7-Dihydro-6- (2-methoxy-4,5-methylenedioxyphenyl) -5H-furo [ 3,2-g ] [ 1 ] benzopyran-5-one

C19H14O6 (338.079)


   

Dolichone

(6aS,13aS) -6a,13a-Dihydro-1,3-dioxolo [ 6,7 ] [ 1 ] benzopyrano [ 3,4-b ] furo [ 3,2-g ] [ 1 ] benzopyran-13 (6H) -one

C19H12O6 (336.0634)


   

12a-Hydroxydolineone

(6aR) -6aalpha,13aalpha-Dihydro-13aalpha-hydroxy-1,3-dioxolo [ 6,7 ] [ 1 ] benzopyrano [ 3,4-b ] furo [ 3,2-g ] [ 1 ] benzopyran-13 (6H) -one

C19H12O7 (352.0583)


   

Neorautone

6- (6-Methoxy-1,3-benzodioxol-5-yl) -7H-furo [ 3,2-g ] [ 1 ] benzopyran-7-one

C19H12O6 (336.0634)


   

Rotenone

Pesticide4_Rotenone_C23H22O6_Furo[2,3:7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-

C23H22O6 (394.1416)


Origin: Plant, Pyrans relative retention time with respect to 9-anthracene Carboxylic Acid is 1.283 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.281 Acquisition and generation of the data is financially supported by the Max-Planck-Society D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals IPB_RECORD: 2241; CONFIDENCE confident structure Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. Rotenone is a mitochondrial electron transport chain complex I inhibitor. Rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production.

   

Pachyrrhizin

Pachyrrhizin

C19H12O6 (336.0634)


   
   

(13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

(13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O6 (336.0634)


   

(1r,13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

(1r,13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O6 (336.0634)


   

6-(2,4,5-trimethoxyphenyl)furo[3,2-g]chromen-7-one

6-(2,4,5-trimethoxyphenyl)furo[3,2-g]chromen-7-one

C20H16O6 (352.0947)


   

(1s,13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

(1s,13r)-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O6 (336.0634)


   

(11r)-11-(6-methoxy-2h-1,3-benzodioxol-5-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

(11r)-11-(6-methoxy-2h-1,3-benzodioxol-5-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

C19H14O6 (338.079)


   

(1s,13s)-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14(19),15,17-heptaen-12-one

(1s,13s)-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14(19),15,17-heptaen-12-one

C20H16O6 (352.0947)


   
   

(1s,6s,13r)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

(1s,6s,13r)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

C23H22O6 (394.1416)


   

(1r,13s)-1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

(1r,13s)-1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O7 (352.0583)


   

(11s)-11-(6-methoxy-2h-1,3-benzodioxol-5-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

(11s)-11-(6-methoxy-2h-1,3-benzodioxol-5-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1(9),2,5,7-tetraen-10-one

C19H14O6 (338.079)


   

(1s,13r)-1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

(1s,13r)-1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

C19H12O7 (352.0583)


   

16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

C23H22O6 (394.1416)


   

(1r,13s)-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14(19),15,17-heptaen-12-one

(1r,13s)-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14(19),15,17-heptaen-12-one

C20H16O6 (352.0947)


   

(1r,6r,13r)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

(1r,6r,13r)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

C23H22O6 (394.1416)