Classification Term: 168408

C27 bile acids, alcohols, and derivatives [ST0403] (ontology term: 23dbd370c926142abd48e36971514745)

C27 bile acids, alcohols, and derivatives [ST0403]

found 64 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Bile acids and derivatives [ST04]

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

(24S)-7alpha,24-Dihydroxycholesterol

(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

C27H46O3 (418.34467659999996)


This compound belongs to the family of Trihydroxy Bile Acids, Alcohols and Derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

   

7-a,25-Dihydroxycholesterol

3beta,7alpha,25-Trihydroxycholest-5-ene

C27H46O3 (418.34467659999996)


7α, 25-dihydroxycholesterol (7α,25-OHC) is a potent and selective agonist and endogenous ligand of the orphan GPCR receptor EBI2 (GPR183). 7α, 25-dihydroxycholesterol is highly potent at activating EBI2 (EC50=140 pM; Kd=450 pM). 7α, 25-dihydroxycholesterol can serve as a chemokine directing migration of B cells, T cells and dendritic cells[1][2].

   

ST 27:2;O2

(22,23-dinor)-24-vinyl-cholest-5-en-3beta,24-diol

C27H44O2 (400.3341124)


   

Scymnol

(24R)-5beta-cholestane-3alpha,7alpha,12alpha,24,26,27-hexol

C27H48O6 (468.3450708)


   

ST 27:2;O3

3beta,5beta-Ketodiol; 2,22,25-Trideoxyecdysone; 3beta,14alpha-Dihydroxy-5beta-cholest-7-en-6-one

C27H44O3 (416.3290274)


   

(25R)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoA

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid

C48H80N7O20P3S (1199.439147)


This compound belongs to the family of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond.

   

(24R,25R)3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestanoyl-CoA

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(2R,3R,6R)-3-hydroxy-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid

C48H80N7O21P3S (1215.4340620000003)


(24R,25R)3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestanoyl-CoA is considered to be slightly soluble (in water) and acidic. (24R,25R)3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestanoyl-CoA is a fatty ester lipid molecule

   

(25S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA

3-phosphoadenosine 5-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-{[(25S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl]sulfanyl}ethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}

C48H80N7O20P3S (1199.439147)


A 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA in which the carbon at position 25 of the steroidal side chain has S configuration.

   

(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol

(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

C27H46O3 (418.34467659999996)


(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is a hydroxysterol and a bile acid intermediate. It is produced from the reaction of 24(R)-Hydroxycholesterol with the enzyme CYP39A, which is also known as 24-hydroxycholesterol 7alpha-hydroxylase (EC 1.14.13.99). This enzyme catalyzes the following reaction: (24R)-cholest-5-ene-3beta,24-diol + NADPH + H+ O2 = (24R)-cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O. This leads to the 7-alpha hydroxylation of 24(R)-hydroxycholesterol. This enzyme can act on both the 24R and 24S isomers. [HMDB] (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is a hydroxysterol and a bile acid intermediate. It is produced from the reaction of 24(R)-Hydroxycholesterol with the enzyme CYP39A, which is also known as 24-hydroxycholesterol 7alpha-hydroxylase (EC 1.14.13.99). This enzyme catalyzes the following reaction: (24R)-cholest-5-ene-3beta,24-diol + NADPH + H+ O2 = (24R)-cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O. This leads to the 7-alpha hydroxylation of 24(R)-hydroxycholesterol. This enzyme can act on both the 24R and 24S isomers.

   

Varanic acid

3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestan-26-oic acid

C27H46O6 (466.3294216)


   

Myxinol

5alpha-Cholestane-3beta,7alpha,16alpha,26-tetrol

C27H48O4 (436.3552408)


   

Arapaimol-B

5beta-Cholestane-2beta,3alpha,7alpha,12alpha,26,27-hexol

C27H48O6 (468.3450708)


   

Latimerol

5alpha-Cholestane-3beta,7alpha,12alpha,26,27-pentol

C27H48O5 (452.3501558)


   

Bufol

5alpha-Cholestane-3alpha,7alpha,12alpha,25,26-pentol

C27H48O5 (452.3501558)


   

Chimaerol

5alpha-Cholestane-3alpha,7alpha,12alpha,24,26-pentol

C27H48O5 (452.3501558)


   

Cyprinol

5alpha-Cholestane-3alpha,7alpha,12alpha,26,27-pentol

C27H48O5 (452.3501558)


   

ST 27:1;O2

5alpha,6alpha-epoxy-5alpha-cholestan-3beta-ol

C27H46O2 (402.34976159999997)


D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D009676 - Noxae > D000963 - Antimetabolites

   

ST 27:0;O3

5alpha-Cholestane-3alpha,7alpha,12alpha-triol

C27H48O3 (420.36032579999994)


   

ST 27:0;O

5beta-Cholestan-3alpha-ol

C27H48O (388.37049579999996)


5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

   

ST 27:1;O

3beta-hydroxymethyl-A-nor-5alpha-cholest-15-ene

C27H46O (386.3548466)


   

ST 27:3;O4

3beta-Hydroxy-5alpha,6alpha-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-al

C27H42O4 (430.30829320000004)


   

ST 27:1;O3

(20R,22R)-20,22-Dihydroxycholesterol;(22R)-20alpha,22-Dihydroxycholesterol

C27H46O3 (418.34467659999996)


7α, 25-dihydroxycholesterol (7α,25-OHC) is a potent and selective agonist and endogenous ligand of the orphan GPCR receptor EBI2 (GPR183). 7α, 25-dihydroxycholesterol is highly potent at activating EBI2 (EC50=140 pM; Kd=450 pM). 7α, 25-dihydroxycholesterol can serve as a chemokine directing migration of B cells, T cells and dendritic cells[1][2].

   

ST 27:0;O2

5alpha-cholest-8(14)-an-3beta,15beta-diol

C27H48O2 (404.36541079999995)


   

ST 27:2;O5

3alpha,7alpha,12alpha-trihydroxy-5alpha-23E-cholesten-26-oic acid

C27H44O5 (448.3188574)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

   

ST 27:0;O5

(25S)-5alpha-cholestan-3beta,6beta,15alpha,16beta,26-pentol

C27H48O5 (452.3501558)


   

ST 27:2;O4

9alpha,11alpha-epoxycholest-7-en-3beta,5alpha,6beta-triol

C27H44O4 (432.3239424)


   

ST 27:3;O3

(22Z)-5alpha,8alpha-epidioxy-24-methyl-27-nor-cholesta-6,22-dien-3beta-ol

C27H42O3 (414.3133782)


   

ST 27:1;O4

(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholestan-26-al

C27H46O4 (434.3395916)


   

ST 27:0;O6

(25S)-5alpha-cholestan-3beta,6alpha,8beta,15alpha,16beat,26-hexol

C27H48O6 (468.3450708)


   

ST 27:2;O6

3alpha,6alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholest-24-en-26-oic acid

C27H44O6 (464.3137724)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

   

ST 27:0;O4

(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetrol

C27H48O4 (436.3552408)


   

ST 27:3;O5

2beta,3beta,20R,22R-tetrahydroxy-cholesta-7,9(11)-dien-6-one

C27H42O5 (446.30320820000003)


   

ST 27:1;O6

26-nor-24-methyl-5alpha-cholest-22E-en-3beta,4,6alpha,8beta,15beta,26-hexol

C27H46O6 (466.3294216)


   

ST 27:1;O5

(3alpha,5beta,7alpha,12alpha,25S)-3,7,12-trihydroxycholestan-26-oic acid

C27H46O5 (450.3345066)


   

ST 27:3;O9

6-oxo-2beta,3beta,14alpha,20R,22R,25-hexahydroxy-5beta-cholest-7-en-26-oic acid

C27H42O9 (510.28286820000005)


   

ST 28:4;O3

5alpha,8alpha-Epidioxyergosta-6,9(11),22E-trien-3beta-ol

C28H42O3 (426.3133782)


   

ST 30:5;O5

(22E,24R)-11alpha-acetoxy-25-hydroxy,5alpha-ergosta-7,22-diene-3,6-dione

C30H44O5 (484.3188574)


   

ST 24:1;O4

3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholan-24-al

C24H40O4 (392.29264400000005)


D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids 3α,12β-Dihydroxycholanoic acid is a bile acid that can be isolated from urine specimens of healthy humans[1].

   

ST 24:1;O6

(23R)-3alpha,7alpha,17alpha,23-Tetrahydroxy-5beta-cholan-24-oic Acid

C24H40O6 (424.28247400000004)


D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids

   

Paricalcitol

(1R,3R,7E)-17beta-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-9,10-secoestra-5,7-diene-1,3-diol

C27H44O3 (416.3290274)


H - Systemic hormonal preparations, excl. sex hormones and insulins > H05 - Calcium homeostasis > H05B - Anti-parathyroid agents D018977 - Micronutrients > D014815 - Vitamins > D004872 - Ergocalciferols

   

ST 26:2;O5

3alpha,7alpha,12alpha-Trihydroxy-5beta-23E-cholestan-26-oic acid

C26H42O5 (434.30320820000003)


   

dafa#1

(+)-(5a,25S)-3-oxocholest-1,7-dien-26-oic acid

C27H40O3 (412.297729)


   

dafa#3

(+)-3a-hydroxy-(5a,25S)-3-oxocholest-7-en-26-oic acid

C27H44O3 (416.3290274)


   

dafa#6

(+)-3a-hydroxy-(5b,25S)-3-oxocholest-7-en-26-oic acid

C27H44O3 (416.3290274)


   

ST 27:3;O2;S

(25S)-3-oxo-cholest-1,4-dien-26-sulfate

C27H42O5S (478.27528020000005)


   

ST 27:4;O2;S

(25S)-3-oxo-cholest-1,4,22E-trien-26-sulfate

C27H40O5S (476.25963100000007)


   

3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oyl-CoA

3-phosphoadenosine 5-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}

C48H80N7O21P3S (1215.4340620000003)


A cholestanoyl-CoA formed by thioester linkage between 3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oic acid and coenzyme A.

   

(24E)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-en-26-oyl-CoA

3-phosphoadenosine 5-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-{[(24E)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-en-26-oyl]sulfanyl}ethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}

C48H78N7O20P3S (1197.4234978)


   

(25R)-3alpha,7alpha-dihydroxy-5beta-cholestan-26-oyl-CoA

3-phosphoadenosine 5-{3-[(3R)-4-({3-[(2-{[(25R)-3alpha,7alpha-dihydroxy-5beta-cholestan-26-oyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}

C48H80N7O19P3S (1183.4442320000003)


   

3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-hydroxy-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

C48H80N7O20P3S (1199.439147)


   

3beta,5alpha,6beta,24R-Tetrahydroxycholestan-(25R)26-oyl CoA

3beta,5alpha,6beta,24R-Tetrahydroxycholestan-(25R)26-oyl CoA

C48H80N7O21P3S (1215.4340620000003)


   

7alpha,24S-Dihydroxy-3-oxocholest-4-en-(25R)26-oyl CoA

7alpha,24S-Dihydroxy-3-oxocholest-4-en-(25R)26-oyl CoA

C48H76N7O20P3S (1195.4078485999999)


   

(25R)-7alpha-hydroxy-3-oxo-4-cholestenoyl CoA

7alpha-hydroxy-3-oxocholest-4-en-(25R)26-oyl CoA

C48H76N7O19P3S (1179.4129336)


   

(25S)-7alpha-hydroxy-3-oxo-4-cholestenoyl CoA

7alpha-hydroxy-3-oxocholest-4-en-(25S)26-oyl CoA

C48H76N7O19P3S (1179.4129336)


   

7alpha-Hydroxy-3,24-bisoxocholest-4-en-(25R)26-oyl-CoA

7alpha-Hydroxy-3,24-bisoxocholest-4-en-(25R)26-oyl-CoA

C48H74N7O20P3S (1193.3921994000002)


   

ST 27:4;O5

7alpha-Hydroxy-3,24-bisoxocholest-4-en-(25R)26-oyl-CoA

C27H40O5 (444.28755900000004)


   

7alpha,24R-Dihydroxy-3-oxocholest-4-en-(25R)26-oyl-CoA

7alpha,24R-Dihydroxy-3-oxocholest-4-en-(25R)26-oyl-CoA

C48H76N7O20P3S (1195.4078485999999)


   

7alpha-Hydroxy-3-oxocholest-4,24(E)-dien-26-oyl-CoA

7alpha-Hydroxy-3-oxocholest-4,24(E)-dien-26-oyl-CoA

C48H74N7O19P3S (1177.3972844)


   

7alpha,24S-dihydroxy-3-oxocholest-4-en-(25S)26-oyl-CoA

7alpha,24S-dihydroxy-3-oxocholest-4-en-(25S)26-oyl-CoA

C48H76N7O20P3S (1195.4078485999999)


   

3b,7b,24R-Trihydroxycholest-5-en-(25R)26-oyl-CoA

3b,7b,24R-Trihydroxycholest-5-en-(25R)26-oyl-CoA

C48H78N7O20P3S (1197.4234978)


   

3b,24R-dihydroxy-7-oxo-cholest-5-en-(25R)26-oyl-CoA

3b,24R-dihydroxy-7-oxo-cholest-5-en-(25R)26-oyl-CoA

C48H76N7O20P3S (1195.4078485999999)


   

Ecdysonic acid

6-oxo-2beta,3beta,14alpha,22R,25-pentahydroxy-5beta-cholest-7-en-26-oic acid

C27H42O8 (494.2879532)


   

(25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA

3-phosphoadenosine 5-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-{[(25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl]sulfanyl}ethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}

C48H80N7O20P3S (1199.439147)


A 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA in which the carbon at position 25 of the steroidal side chain has R configuration.

   

(24R,25R)-3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-CoA

3-phosphoadenosine 5-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-{[(24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oyl]sulfanyl}ethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}

C48H80N7O21P3S (1215.4340620000003)


An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oic acid.