Classification Term: 168587

Acyclic triterpenoids [PR010601] (ontology term: 8638bc36cc7bce6432952442ddaf99f5)

Acyclic triterpenoids [PR010601]

found 44 associated metabolites at molecular_framework metabolite taxonomy ontology rank level.

Ancestor: C30 isoprenoids (triterpenes) [PR0106]

Child Taxonomies: There is no child term of current ontology term.

Squalene

InChI=1/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24

C30H50 (410.39123)


Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

   

Dehydrosqualene

(6E,10E,12Z,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,12,14,18,22-heptaene

C30H48 (408.37558079999997)


   

4,4-Diaponeurosporenic acid

2,6,10,15,19,23-hexamethyltetracosa-2E,4E,6E,8E,10E,12E,14E,16E,18E,22-decaenoic acid

C30H40O2 (432.302814)


   

Glucosyl-4,4-diaponeurosporenoate

alpha-D-glucopyranosyl 2,6,10,15,19,23-hexamethyltetracosa-2E,4E,6E,8E,10E,12E,14E,16E,18E,22-decaenoate

C36H50O7 (594.355635)


   

Staphyloxanthin

2,6,10,15,19,23-hexamethyltetracosa-2E,4E,6E,8E,10E,12E,14E,16E,18E,22-decaenoyl]-6-O-(12-methyltetradecanoyl)-beta-D-glucopyranose

C51H78O8 (818.5696388)


A xanthophyll that is beta-D-glucopyranose in which the hydroxy groups at positions 1 and 6 have been acylated by an all-trans-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoyl group and a 12-methyltetradecanoyl group, respectively. Staphyloxanthin is responsible for the characteristic yellow-golden colour which gives the bacterium Staphylococcus aureus its name. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

4,4-Diapolycopenedial

(all-E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,20,22-undecaenedial

C30H36O2 (428.2715156)


   

4,4-Diaponeurosporen-4-al

2,6,10,15,19,23-hexamethyltetracosa-2E,4E,6E,8E,10E,12E,14E,16E,18E,22-decaenal

C30H40O (416.307899)


   

4-Hydroxy-4,4-diaponeurosporene

7,8-Dihydro-4,4-diapo-psi,psi-caroten-4-ol

C30H42O (418.3235482)


   

4,4-Diapo-7,8,11,12-tetrahydrolycopene

7,8,11,12-Tetrahydro-4,4-diapo-psi,psi-carotene

C30H44 (404.3442824)


   

3S-squalene-2,3-epoxide

2,3S-epoxy-2,6,10,15,19,23-hexamethyltetracosa-6E,10E,14E,18E,22-pentaene

C30H50O (426.386145)


   

Tetrahydrosqualene

Tetrahydrosqualene

C30H54 (414.4225284)


   

C30:6 Highly branched isoprenoid A

2,6,10,14,18-pentamethyl-13E-(3-methyl-pent-4-enylidene)-nonadeca-2,6E,10Z,17-tetraene

C30H50 (410.39123)


   

C30:6 Highly branched isoprenoid B

2,6,10,14,18-pentamethyl-13E-(3-methyl-pent-4-enylidene)-nonadeca-2,6E,10E,17-tetraene

C30H50 (410.39123)


   

C30:5 Monocyclic highly branched isoprenoid B

2,6,10,14,18-pentamethyl-13E-(3-methyl-pent-4-enylidene)-nonadeca-2,6E,10E-triene

C30H52 (412.4068792)


   

C30:5 Highly branched isoprenoid

2,6,10,14,18-pentamethyl-13E-(3-methyl-pent-4-enylidene)-nonadeca-2,6E,10Z-triene

C30H52 (412.4068792)


   

C30 Highly branched isoprenoid

2,6,10,14,18-pentamethyl-7-(3-methyl-pentyl)-nonadecane

C30H62 (422.48512519999997)


   

Presqualene diphosphate

Presqualene diphosphate

C30H52O7P2 (586.3188102)


A triterpenyl phosphate that is presqualene in which the hydroxy hydrogen has been replaced by a diphosphate group.

   

2-OOH-SQ

2-hydroperoxy-2,6,10,15,19,23-hexamethyltetracosa-3E,6E,10E,14E,18E,22-hexaene

C30H50O2 (442.38106)


   

11-OOH-SQ

11-hydroperoxy-10-methylene-2,6,15,19,23-pentamethyltetracosa-2,6E,14E,18E,22-pentaene

C30H50O2 (442.38106)


   

3-OOH-SQ

3-hydroperoxy-2,6,10,15,19,23-hexamethyltetracosa-1,6E,10E,14E,18E,22-hexaene

C30H50O2 (442.38106)


   

6-OOH-SQ

6-hydroperoxy-2,6,10,15,19,23-hexamethyltetracosa-2,7E,10E,14E,18E,22-hexaene

C30H50O2 (442.38106)


   

7-OOH-SQ

7-hydroperoxy-6-methylene-2,10,15,19,23-pentamethyltetracosa-2,10E,14E,18E,22-pentaene

C30H50O2 (442.38106)


   

10-OOH-SQ

10-hydroperoxy-2,6,10,15,19,23-hexamethyltetracosa-2,6E,11E,14E,18E,22-hexaene

C30H50O2 (442.38106)


   

Diepoxysqualene

2,3S:22S,23-diepoxysqualene

C30H50O2 (442.38106)


   
   

Hydroxy-3,4-dehydro-apo-8-lycopene

1-Hydroxy-3,4-didehydro-1,2-dihydro-8-apo-psi-carotene

C30H42O (418.3235482)


   

4-(D-Glucopyranosyloxy)-4,4-diaponeurosporene

4-(D-Glucopyranosyloxy)-7,8-dihydro-4,4-diapo-psi,psi-carotene

C36H52O6 (580.3763692)


   

1-Hexosyl-1,2-dihydro-3,4-didehydroapo-8-lycopenol

1-Mannosyloxy-3,4-didehydro-1,2-dihydro-8-apo-psi-caroten-8-ol

C36H52O7 (596.3712842)


   

1-(D-Mannosyloxy)-3,4-didenhydro-1,2-dihydro-8-apolycopen-8-oic acid

1-(D-Mannosyloxy)-3,4-didenhydro-1,2-dihydro-8-apo-psi,psi-carotene-8-oic acid methyl ester

C37H52O8 (624.3661992)


   

4,4-Diapolycopen-4-al

4,4-Diapo-psi,psi-caroten-4-al

C30H38O (414.2922498)


An apo carotenoid triterpenoid that is 4,4-diapolycopene in which one of the terminal methyl groups has been replaced by a formyl group.

   

Hydroxy-diaponeurosporenal

4,4-Diapo-7,8-dihydro-4-hydroxy-psi,psi-carotene-4-al

C30H40O2 (432.302814)


   

4,4-Diapocaroten-4-al-4-oic acid

4-Oxo-4,4-diapo-psi,psi-caroten-4-oic acid

C30H36O3 (444.26643060000004)


   

4,4-Diaplycopene-4,4-dioic acid

4,4-Diapo-psi,psi-carotene-4,4-dioic acid

C30H36O4 (460.2613456)


   

4,4-Diapocarotenoic acid

4,4-Diapo-psi,psi-caroten-4-oic acid

C30H38O2 (430.28716479999997)


   

4-Hydroxy-4,4-diaponeurosporene-4-oic acid

7,8-Dihydro-4-hydroxy-4,4-diapo-psi,psi-caroten-4-oic acid

C30H40O3 (448.297729)


   

Methyl 4,4-diapolycopene-dioate

Methyl-4,4-diapo-psi,psi-carotene-4,4-dioic acid

C31H38O4 (474.2769948)


   

Methyl hydroxy-3,4-dehydro-apo-8-lycopenoate

Methyl 1-hydroxy-3,4-didehydro-1,2-dihydro-8-apo-psi-caroten-8-oate

C31H42O3 (462.3133782)


   

Acetyl-4,4-diapolycopene-4,4-dioate

Acetyl-4,4-diapo-psi,psi-carotene-4,4-dioic acid

C32H38O5 (502.2719098)


   

4-(beta-D-Glucopyranosyloxy)-7,8-dihydro-4,4-diapo-psi,psi-caroten-4-oic acid

4-(beta-D-Glucopyranosyloxy)-7,8-dihydro-4,4-diapo-psi,psi-caroten-4-oic acid

C36H48O8 (608.3349008)


   

Methyl mannosyl-3,4-dehydro-apo-8-lycopenoate

Methyl 1-mannosyloxy-3,4-didehydro-1,2-dihydro-8-apo-psi-caroten-8-oate

C37H52O8 (624.3661992)


   

Methyl glucosyl-3,4-dehydro-apo-8-lycopenoate

Methyl 1-glucosyloxy-3,4-didehydro-1,2-dihydro-8-apo-psi-caroten-8-oate

C37H52O8 (624.3661992)


   

Glucopyranosyl-1-O-(4,4-diapo-7,8,11,12-tetrahydrolycopen-4-oate)-6-O-(2-methylbutanoate)

4-[(6-O-11-tetranoyl-b-D-glucopyranosyl)oxy]-7,8-dihydro-4,4-diapo-psi,psi-carotene-4-oic acid

C41H60O8 (680.428796)


   

Diapolycopenedioic acid diglucosyl ester

4,4-Di(beta-D-glucopyranosyl)-4,4-diapo-psi,psi-carotene-4,4-dioate

C42H56O14 (784.3669876)


   

Squalene cyclic peroxide

6-(2-hydroperoxypropan-2-yl)-3-methyl-3-((1E,4E,8E,12E)-4,9,13,17-tetramethyloctadeca-1,4,8,12,16-pentaen-1-yl)-1,2-dioxane

C30H50O4 (474.37089000000003)