NCBI Taxonomy: 1279479

Rhizopus arrhizus Type I NRRL 21789 (ncbi_taxid: 1279479)

found 40 associated metabolites at strain taxonomy rank level.

Ancestor: Rhizopus arrhizus

Child Taxonomies: none taxonomy data.

Fumarate

(2E)-but-2-enedioic acid

C4H4O4 (116.011)


Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses. Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-). Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. Fumarate has recently been recognized as an oncometabolite. (A15199). As a food additive, fumaric acid is used to impart a tart taste to processed foods. It is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. It is used to impart a sour taste to sourdough and rye bread. In cake mixes, it is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, it helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Aspergillus. Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. Fumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-17-8 (retrieved 2024-07-01) (CAS RN: 110-17-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

   

Ergosterol peroxide

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

   

Ergosterol peroxide

Ergosterol peroxide

C28H44O3 (428.329)


   

Fumaric Acid

(2Z)-2-Butenedioic acid

C4H4O4 (116.011)


Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

   

n-[(1s)-3-amino-1-{[(1s,2r)-1-{[(1s)-3-amino-1-{[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-2,5,8,11,14,17,20-heptahydroxy-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-c-hydroxycarbonimidoyl}propyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}propyl]-5-methylheptanimidic acid

n-[(1s)-3-amino-1-{[(1s,2r)-1-{[(1s)-3-amino-1-{[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-2,5,8,11,14,17,20-heptahydroxy-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-c-hydroxycarbonimidoyl}propyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}propyl]-5-methylheptanimidic acid

C52H98N16O13 (1154.7499)


   

6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-ol

6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-ol

C20H34O2 (306.2559)


   

(2r,3s,4s,5s)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-5-(hydroxymethyl)oxolane-3,4-diol

(2r,3s,4s,5s)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-5-(hydroxymethyl)oxolane-3,4-diol

C25H42O6 (438.2981)


   

methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

C31H50O3 (470.376)


   

(1r,2s,7s,8s,10r,12s,13s)-8,13-dihydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

(1r,2s,7s,8s,10r,12s,13s)-8,13-dihydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

C20H32O3 (320.2351)


   

(1r,2s,7s,9s,10s,12s)-9-hydroxy-13-(hydroxymethyl)-2,6,6-trimethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

(1r,2s,7s,9s,10s,12s)-9-hydroxy-13-(hydroxymethyl)-2,6,6-trimethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

C20H30O3 (318.2195)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

C20H34O2 (306.2559)


   

9-hydroxy-13-(hydroxymethyl)-2,6,6-trimethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

9-hydroxy-13-(hydroxymethyl)-2,6,6-trimethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

C20H30O3 (318.2195)


   

n-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-2,5,8,11,14,17,20-heptahydroxy-3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-c-hydroxycarbonimidoyl}propyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)propyl]-5-methylheptanimidic acid

n-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-2,5,8,11,14,17,20-heptahydroxy-3-(1-hydroxyethyl)-12,15-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclotricosa-1,4,7,10,13,16,19-heptaen-21-yl]-c-hydroxycarbonimidoyl}propyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)propyl]-5-methylheptanimidic acid

C52H98N16O13 (1154.7499)


   

(1r,2s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-ene

(1r,2s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-ene

C20H32 (272.2504)


   

(1r,2s,4s,7s,9s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

(1r,2s,4s,7s,9s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

C20H34O3 (322.2508)


   

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)oxane-3,4,5-triol

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)oxane-3,4,5-triol

C25H42O6 (438.2981)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

C20H30O (286.2297)


   

(1r,2s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

(1r,2s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-one

C20H30O (286.2297)


   

(1r,2s,7s,10s,12s,13s)-13-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

(1r,2s,7s,10s,12s,13s)-13-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

C20H32O2 (304.2402)


   

(1r,2s,4s,7s,10s,12s,13r)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

(1r,2s,4s,7s,10s,12s,13r)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

C20H34O2 (306.2559)


   

(2s,3r,4s,5s,6r)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C26H44O7 (468.3087)


   

methyl (1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

methyl (1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

C31H50O3 (470.376)


   

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)-5-(hydroxymethyl)oxolane-3,4-diol

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)-5-(hydroxymethyl)oxolane-3,4-diol

C25H42O6 (438.2981)


   

(1r,2s,4s,7s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

(1r,2s,4s,7s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,13-diol

C20H34O2 (306.2559)


   

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H60O6 (576.439)


   

(1r,2s,4r,7s,9s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

(1r,2s,4r,7s,9s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

C20H34O3 (322.2508)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

C20H32O (288.2453)


   

(2r,3s,4r,5s)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-5-(hydroxymethyl)oxolane-3,4-diol

(2r,3s,4r,5s)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}-5-(hydroxymethyl)oxolane-3,4-diol

C25H42O6 (438.2981)


   

(1r,2s,7s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-ol

(1r,2s,7s,10s,12s,13s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-ol

C20H34O (290.261)


   

(1r,2s,4s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

(1r,2s,4s,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

C20H32O (288.2453)


   

(1r,2s,4r,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

(1r,2s,4r,7s,10s,12s)-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-en-4-ol

C20H32O (288.2453)


   

(2r,3s,4r,5r)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}oxane-3,4,5-triol

(2r,3s,4r,5r)-2-{[(1r,2s,4s,7s,10s,12s,13s)-4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl]oxy}oxane-3,4,5-triol

C25H42O6 (438.2981)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-ol

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-ol

C20H34O (290.261)


   

13-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

13-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

C20H32O2 (304.2402)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecane-4,9,13-triol

C20H34O3 (322.2508)


   

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

2-({4-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-13-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C26H44O7 (468.3087)


   

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-ene

2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-13-ene

C20H32 (272.2504)


   

5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


   

(1r,2s,6r,7r,10s,12r,13r)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-ol

(1r,2s,6r,7r,10s,12r,13r)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-ol

C20H34O2 (306.2559)


   

8,13-dihydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

8,13-dihydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadecan-4-one

C20H32O3 (320.2351)