NCBI Taxonomy: 70109

Penicillium paxilli (ncbi_taxid: 70109)

found 40 associated metabolites at species taxonomy rank level.

Ancestor: Penicillium

Child Taxonomies: Penicillium paxilli ATCC 26601

Geranylgeranyl-PP

{[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

C20H36O7P2 (450.1936)


Geranylgeranyl pyrophosphate, also known as geranylgeranyl-PP or GGPP, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. This compound belongs to the family of acyclic diterpenes. These are diterpenes (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, GGPP is considered to be an isoprenoid lipid molecule. GGPP is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranylgeranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. [HMDB]. Geranylgeranyl-PP is found in many foods, some of which are burdock, longan, calabash, and cloves.

   

TR 1 toxin

verruculogen

C27H33N3O7 (511.2318)


   

Paxilline

2H-1-Benzopyrano(5,6:6,7)indeno(1,2-b)indol-3(4bh)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2-alpha,4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-

C27H33NO4 (435.2409)


Paxilline is an indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels. It has a role as a mycotoxin, a Penicillium metabolite, an anticonvulsant, an Aspergillus metabolite, a potassium channel blocker, a genotoxin, a geroprotector and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterohexacyclic compound, a tertiary alcohol, a terpenoid indole alkaloid, an enone and a diterpene alkaloid. Paxilline is a natural product found in Penicillium thiersii, Aspergillus foveolatus, and other organisms with data available. Tremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels. Tremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata D002317 - Cardiovascular Agents > D026902 - Potassium Channel Blockers D049990 - Membrane Transport Modulators Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5 μM and 50 μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

   

3-Geranylgeranylindole; 3-(Geranylgeranyl)indole

1H-Indole, 3-(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-

C28H39N (389.3082)


   
   

Dehydroxypaxilline

(1S,2S,5S,7R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO3 (419.246)


Dehydroxypaxilline is a metabolite of Emericella striata. Metabolite of Emericella striata

   

PC-M6

(1S,2S,5S,7S,8R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17(22),18,20-pentaen-8-ol

C27H35NO3 (421.2617)


Tremorgenic mycotoxin from Penicillium crustosum, Penicillium paxilli and Acremonium lolii. Tremorgenic mycotoxin from Penicillium crustosum, Penicillium paxilli and Acremonium lolii

   
   

alpha-PC-M6

alpha-10-Hydroxy-12-demethyl-11,12-dehydropaspaline

C27H35NO3 (421.2617)


   

14alpha-Hydroxy-4beta-deoxypaxilline

5-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO4 (435.2409)


14alpha-Hydroxy-4beta-deoxypaxilline is a metabolite of Penicillium paxilli and Acremonium lolii. Metabolite of Penicillium paxilli and Acremonium lolii

   

Geranylgeraniol diphosphate

({hydroxy[(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)oxy]phosphoryl}oxy)phosphonic acid

C20H36O7P2 (450.1936)


   

beta-PC-M6

beta-10-Hydroxy-12-demethyl-11,12-dehydropaspaline

C27H35NO3 (421.2617)


   

Dehydroxypaxilline

7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO3 (419.246)


   

Paxilline

NCGC00025342-07_C27H33NO4_(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5,6:6,7]indeno[1,2-b]indol-3(4bH)-one

C27H33NO4 (435.2409)


Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5 μM and 50 μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

   

verruculogen

verruculogen

C27H33N3O7 (511.2318)


An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species. CONFIDENCE Penicillium amphipolaria

   

Geranylgeranyl diphosphate

3,7,11,15-tetramethyl-2Z,6Z,10Z,14-hexadecatetraen-1-ol diphosphate

C20H36O7P2 (450.1936)


   

1H-Indole, 3-(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-

1H-Indole, 3-(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-

C28H39N (389.3082)


   

(1s,2s,5s,7s,10r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-10-carbaldehyde

(1s,2s,5s,7s,10r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-10-carbaldehyde

C28H37NO3 (435.2773)


   

5-(but-2-enoyl)-4-methoxy-6-methylpyran-2-one

5-(but-2-enoyl)-4-methoxy-6-methylpyran-2-one

C11H12O4 (208.0736)


   

(1s,2r,5s,7r,11s,14s)-5,11-dihydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

(1s,2r,5s,7r,11s,14s)-5,11-dihydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO5 (451.2359)


   

6,21-dimethyl-21-(4-methyl-3-methylidenepentyl)-14,18,20-trioxaheptacyclo[15.4.1.0²,¹⁶.0²,¹⁹.0⁵,¹⁵.0⁶,¹¹.0¹³,¹⁵]docosan-9-ol

6,21-dimethyl-21-(4-methyl-3-methylidenepentyl)-14,18,20-trioxaheptacyclo[15.4.1.0²,¹⁶.0²,¹⁹.0⁵,¹⁵.0⁶,¹¹.0¹³,¹⁵]docosan-9-ol

C28H42O4 (442.3083)


   

7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

C27H35NO3 (421.2617)


   

5,11-dihydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

5,11-dihydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO5 (451.2359)


   

5-[(3s)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

5-[(3s)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

C11H14O5 (226.0841)


   

(1s,2s,5s,7s,8s,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

(1s,2s,5s,7s,8s,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

C27H35NO3 (421.2617)


   

7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-10-carbaldehyde

7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-10-carbaldehyde

C28H37NO3 (435.2773)


   

(1s,2s,5s,7r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

(1s,2s,5s,7r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO3 (419.246)


   

(1s,2s,5s,7r,11r,14s)-5-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

(1s,2s,5s,7r,11r,14s)-5-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO4 (435.2409)


   

(1s,2s,5r,6s,9s,11r,13s,15s,16s,17r,19s,21s)-6,21-dimethyl-21-(4-methyl-3-methylidenepentyl)-14,18,20-trioxaheptacyclo[15.4.1.0²,¹⁶.0²,¹⁹.0⁵,¹⁵.0⁶,¹¹.0¹³,¹⁵]docosan-9-ol

(1s,2s,5r,6s,9s,11r,13s,15s,16s,17r,19s,21s)-6,21-dimethyl-21-(4-methyl-3-methylidenepentyl)-14,18,20-trioxaheptacyclo[15.4.1.0²,¹⁶.0²,¹⁹.0⁵,¹⁵.0⁶,¹¹.0¹³,¹⁵]docosan-9-ol

C28H42O4 (442.3083)


   

5-[(3r)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

5-[(3r)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

C11H14O5 (226.0841)


   

4-methoxy-5-methyl-6-[(3r)-3-sulfanylbutanoyl]pyran-2-one

4-methoxy-5-methyl-6-[(3r)-3-sulfanylbutanoyl]pyran-2-one

C11H14O4S (242.0613)


   

5-[(2e)-but-2-enoyl]-4-methoxy-6-methylpyran-2-one

5-[(2e)-but-2-enoyl]-4-methoxy-6-methylpyran-2-one

C11H12O4 (208.0736)


   

(1s,2r,5s,6r,10r,13s)-6,10-dihydroxy-1,2-dimethyl-22-azahexacyclo[11.10.0.0²,¹⁰.0⁵,⁹.0¹⁵,²³.0¹⁶,²¹]tricosa-8,15(23),16,18,20-pentaen-7-one

(1s,2r,5s,6r,10r,13s)-6,10-dihydroxy-1,2-dimethyl-22-azahexacyclo[11.10.0.0²,¹⁰.0⁵,⁹.0¹⁵,²³.0¹⁶,²¹]tricosa-8,15(23),16,18,20-pentaen-7-one

C24H27NO3 (377.1991)


   

3-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1h-indole

3-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1h-indole

C28H39N (389.3082)


   

4-methoxy-5-methyl-6-(3-sulfanylbutanoyl)pyran-2-one

4-methoxy-5-methyl-6-(3-sulfanylbutanoyl)pyran-2-one

C11H14O4S (242.0613)


   

5-(3-hydroxybutanoyl)-4-methoxy-6-methylpyran-2-one

5-(3-hydroxybutanoyl)-4-methoxy-6-methylpyran-2-one

C11H14O5 (226.0841)


   

(1s,2s,5s,7s,8r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

(1s,2s,5s,7s,8r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol

C27H35NO3 (421.2617)


   

(9s,14r,17r,23s,24r)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2,4,6-tetraene-16,22-dione

(9s,14r,17r,23s,24r)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2,4,6-tetraene-16,22-dione

C27H33N3O7 (511.2318)


   

11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

C27H33NO4 (435.2409)


   

2-[(1s,2s,5s,7s,10s,11r,14s)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

2-[(1s,2s,5s,7s,10s,11r,14s)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

C28H39NO2 (421.2981)