NCBI Taxonomy: 38005

Tolypocladium cylindrosporum (ncbi_taxid: 38005)

found 56 associated metabolites at species taxonomy rank level.

Ancestor: Tolypocladium

Child Taxonomies: none taxonomy data.

3-Hydroxyisobutyric acid

3-Hydroxyisobutyric acid

C4H8O3 (104.0473418)


A 4-carbon, branched hydroxy fatty acid and intermediate in the metabolism of valine. 3-Hydroxyisobutyric acid is an important interorgan metabolite, an intermediate in the pathways of l-valine and thymine and a good gluconeogenic substrate.

   
   

3-Hydroxyisobutyric acid

3-Hydroxy-2-methyl-(S)-propanoic acid

C4H8O3 (104.0473418)


(S)-3-Hydroxyisobutyric acid (3-HIBA) (CAS: 2068-83-9) is an organic acid. 3-HIBA is an intermediate in L-valine metabolism. 3-HIBA plays an important role in the diagnosis of the very rare inherited metabolic diseases 3-hydroxyisobutyric aciduria (OMIM: 236795) and methylmalonic semialdehyde dehydrogenase deficiency (OMIM: 603178). Patients with 3-hydroxyisobutyric aciduria excrete a significant amount of 3-HIBA not only during the acute stage but also when stable. 3-Hydroxyisobutyric aciduria is caused by a 3-hydroxyisobutyryl-CoA dehydrogenase deficiency (PMID: 18329219). The severity of this disease varies from case to case. Most patients exhibit dysmorphic features, such as a small triangular face, a long philtrum, low set ears, and micrognathia (PMID: 10686279). Lactic acidemia is also found in the affected patients, indicating that mitochondrial dysfunction is involved. 3-HIBA appears to specifically inhibit the function of the respiratory chain complex I-III and mitochondrial creatine kinase (PMID: 18329219). BioTransformer predicts that 3-HIBA is a product of 2-methylpropanoic acid metabolism via a hydroxylation-of-terminal-methyl reaction catalyzed by CYP2B6 and CYP2E1 enzymes (PMID: 30612223). (S)-3-Hydroxyisobutyric (3-HIBA) acid is an organic acid. 3-HIBA is an intermediate in the metabolic pathways of L-valine and L-thymine amino acids. 3-HIBA plays an important role in the diagnosis of the very rare inherited metabolic diseases 3-hydroxyisobutyric aciduria (OMIM 236795) and methylmalonic semialdehyde dehydrogenase deficiency (OMIM 603178). Patients with 3-hydroxyisobutyric aciduria excrete a significant amount of 3-HIBA not only during the acute stage but also when stable. The deficient enzyme in 3HiB-uria remains unclear. The severity of this disease varies from case to case. Most patients exhibit dysmorphic features, such as a small triangular face, a long philtrum, low set ears and micrognathia (PMID: 113770040, 10686279) [HMDB] 3-Hydroxyisobutyric acid is an important interorgan metabolite, an intermediate in the pathways of l-valine and thymine and a good gluconeogenic substrate.

   

(2s,4s,6z)-1-[(5z)-2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl]-2,4-dimethyloct-6-en-1-one

(2s,4s,6z)-1-[(5z)-2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl]-2,4-dimethyloct-6-en-1-one

C21H25NO4 (355.178349)


   

(2s,4e)-5-hydroxy-2-[(s)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

(2s,4e)-5-hydroxy-2-[(s)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(4e)-5-hydroxy-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

(4e)-5-hydroxy-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

C21H25NO4 (355.178349)


   

5-hydroxy-2-[hydroxy(4-hydroxyphenyl)methyl]-4-(1-hydroxy-2,4-dimethyloct-6-en-1-ylidene)-2h-pyrrol-3-one

5-hydroxy-2-[hydroxy(4-hydroxyphenyl)methyl]-4-(1-hydroxy-2,4-dimethyloct-6-en-1-ylidene)-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(6r,6ar,8r,10s,10ar)-4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

(6r,6ar,8r,10s,10ar)-4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

C21H25NO3 (339.18343400000003)


   

3,8-dihydroxy-4-(4-hydroxyphenyl)-6-methylchromen-2-one

3,8-dihydroxy-4-(4-hydroxyphenyl)-6-methylchromen-2-one

C16H12O5 (284.0684702)


   

3-[(2s,4r,6s)-2-ethenyl-4,6-dimethylcyclohexyl]pyridine-2,4-diol

3-[(2s,4r,6s)-2-ethenyl-4,6-dimethylcyclohexyl]pyridine-2,4-diol

C15H21NO2 (247.15722060000002)


   

(6ar,8r,10s,10ar)-4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

(6ar,8r,10s,10ar)-4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

C21H25NO3 (339.18343400000003)


   

(2r,4e)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

(2r,4e)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(2z,4e)-5-hydroxy-4-[(2r,4r,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

(2z,4e)-5-hydroxy-4-[(2r,4r,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

C21H25NO4 (355.178349)


   

(2r)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

(2r)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-21-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-21-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

C32H45NO7 (555.3195860000001)


   

4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

C21H25NO3 (339.18343400000003)


   

(4e)-5-hydroxy-4-[(2r,4r)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

(4e)-5-hydroxy-4-[(2r,4r)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

C21H25NO4 (355.178349)


   

(1s,2s,5s,7s,9r,10r,11r,14s)-7-(2-hydroxypropan-2-yl)-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-9-ol

(1s,2s,5s,7s,9r,10r,11r,14s)-7-(2-hydroxypropan-2-yl)-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-9-ol

C28H39NO3 (437.29297840000004)


   

1-[(1r,2s,13s,16s,17s,19r,20r,22s,25s,27s)-22-(1,2-dihydroxy-2-methylpropyl)-16-hydroxy-1,2,24,24-tetramethyl-18,21,23,26-tetraoxa-4-azaoctacyclo[14.13.0.0²,¹³.0³,¹¹.0⁵,¹⁰.0¹⁷,¹⁹.0¹⁷,²⁷.0²⁰,²⁵]nonacosa-3(11),5,7,9-tetraen-7-yl]-3-methylbutane-2,3-diol

1-[(1r,2s,13s,16s,17s,19r,20r,22s,25s,27s)-22-(1,2-dihydroxy-2-methylpropyl)-16-hydroxy-1,2,24,24-tetramethyl-18,21,23,26-tetraoxa-4-azaoctacyclo[14.13.0.0²,¹³.0³,¹¹.0⁵,¹⁰.0¹⁷,¹⁹.0¹⁷,²⁷.0²⁰,²⁵]nonacosa-3(11),5,7,9-tetraen-7-yl]-3-methylbutane-2,3-diol

C37H53NO9 (655.3720128)


   

1-{2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl}-2,4-dimethyloct-6-en-1-one

1-{2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl}-2,4-dimethyloct-6-en-1-one

C21H25NO4 (355.178349)


   

3-[(2s,4r,6s)-2-ethenyl-4,6-dimethylcyclohexyl]-1,4-dihydroxypyridin-2-one

3-[(2s,4r,6s)-2-ethenyl-4,6-dimethylcyclohexyl]-1,4-dihydroxypyridin-2-one

C15H21NO3 (263.1521356)


   

3-(acetyloxy)-2-methylpropanoic acid

3-(acetyloxy)-2-methylpropanoic acid

C6H10O4 (146.057906)


   

2-(hydroxymethyl)-2-methyl-3-oxobutanoic acid

2-(hydroxymethyl)-2-methyl-3-oxobutanoic acid

C6H10O4 (146.057906)


   

(2r,4r,6z)-1-[(5z)-2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl]-2,4-dimethyloct-6-en-1-one

(2r,4r,6z)-1-[(5z)-2,4-dihydroxy-5-[(4-hydroxyphenyl)methylidene]pyrrol-3-yl]-2,4-dimethyloct-6-en-1-one

C21H25NO4 (355.178349)


   

(2s,4e)-5-hydroxy-2-[(s)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

(2s,4e)-5-hydroxy-2-[(s)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(2r,4e)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

(2r,4e)-5-hydroxy-2-[(r)-hydroxy(4-hydroxyphenyl)methyl]-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2h-pyrrol-3-one

C21H27NO5 (373.18891320000006)


   

(2z,4e)-5-hydroxy-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

(2z,4e)-5-hydroxy-4-[(2s,4s,6z)-1-hydroxy-2,4-dimethyloct-6-en-1-ylidene]-2-[(4-hydroxyphenyl)methylidene]pyrrol-3-one

C21H25NO4 (355.178349)