Signaling by Retinoic Acid

Das BC, Thapa P, Karki R, Das S, Mahapatra S, Liu T, Torregroza I, Wallace DP, Kambhampati S, Van Veldhuizen P, Verma A, Ray SK, Evans T. Retinoic acid signaling pathways in development and diseases. Bioorganic & Medicinal Chemistry. 2014 Jan;22(2):673–83. doi: 10.1016/j.bmc.2013.11.025.; Harrison EH. Mechanisms involved in the intestinal absorption of dietary vitamin A and provitamin A carotenoids. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 2012 Jan;1821(1):70–7. doi: 10.1016/j.bbalip.2011.06.002.; Napoli JL. Physiological insights into all-trans-retinoic acid biosynthesis. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 2012 Jan;1821(1):152–67. doi: 10.1016/j.bbalip.2011.05.004.; Catharine Ross A, Zolfaghari R. Cytochrome P450s in the Regulation of Cellular Retinoic Acid Metabolism. Annu. Rev. Nutr. 2011 Aug 21;31(1):65–87. doi: 10.1146/annurev-nutr-072610-145127.

Metabolites

11-cis-Retinal

Formula: C20H28O (284.2140038)

CAS ID: 564-87-4

11-cis-Retinol

Formula: C20H30O (286.229653)

CAS ID: 22737-96-8

9-cis-Retinal

Formula: C20H28O (284.2140038)

CAS ID: 514-85-2

9-cis-Retinoic acid

Formula: C20H28O2 (300.2089188)

CAS ID: 5300-03-8

all-trans-4-Hydroxyretinoic acid

Formula: C20H28O3 (316.2038338)

CAS ID: 66592-72-1

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

NADP+

Formula: C21H29N7O17P3 (744.0832754)

CAS ID: 53-59-8

NADPH

Formula: C21H30N7O17P3 (745.0911)

CAS ID: 2646-71-1

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Potassium cation

Formula: K (38.963708)

CAS ID: 24203-36-9

Retinal

Formula: C20H28O (284.2140038)

CAS ID: 116-31-4

Retinoate

Formula: C20H28O2 (300.2089188)

CAS ID: 302-79-4

Retinol

Formula: C20H30O (286.229653)

CAS ID: 68-26-8

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

Acitretin

Formula: C21H26O3 (326.1881846)

CAS ID: 55079-83-9

9-cis-4-hydroxyretinoic acid

Formula: C20H28O3 (316.2038338)

CAS ID:

dichloroacetate

Formula: C2HCl2O2 (126.93536060000001)

CAS ID: 13425-80-4

pyruvate

Formula: C3H3O3 (87.00821880000001)

CAS ID: 57-60-3

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

thiamine(1+) diphosphate(3-)

Formula: C12H16N4O7P2S (422.0214926)

CAS ID:

NADH(2-)

Formula: C21H27N7O14P2 (663.1091182000001)

CAS ID:

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

ADP(3-)

Formula: C10H12N5O10P2 (424.0059412)

CAS ID:

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.1.1.1 alcohol dehydrogenase alcohol:NAD+ oxidoreductase
1.1.1.105 all-trans-retinol dehydrogenase (NAD+) all-trans retinol:NAD+ oxidoreductase
1.1.1.300 NADP-retinol dehydrogenase retinol:NADP+ oxidoreductase
1.14.14.1 unspecific monooxygenase substrate,NADPH-hemoprotein reductase:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
1.2.1.19 aminobutyraldehyde dehydrogenase 4-aminobutanal:NAD+ 1-oxidoreductase
1.2.1.28 benzaldehyde dehydrogenase (NAD+) benzaldehyde:NAD+ oxidoreductase
1.2.1.3 aldehyde dehydrogenase (NAD+) aldehyde:NAD+ oxidoreductase
1.2.1.32 aminomuconate-semialdehyde dehydrogenase 2-aminomuconate-6-semialdehyde:NAD+ 6-oxidoreductase
1.2.1.36 retinal dehydrogenase retinal:NAD+ oxidoreductase
1.2.4.1 pyruvate dehydrogenase (acetyl-transferring) pyruvate:[dihydrolipoyllysine-residue acetyltransferase]-lipoyllysine 2-oxidoreductase (decarboxylating, acceptor-acetylating)
1.8.1.4 dihydrolipoyl dehydrogenase protein-N6-(dihydrolipoyl)lysine:NAD+ oxidoreductase
2.3.1.12 dihydrolipoyllysine-residue acetyltransferase acetyl-CoA:enzyme N6-(dihydrolipoyl)lysine S-acetyltransferase
2.7.11.2 [pyruvate dehydrogenase (acetyl-transferring)] kinase ATP:[pyruvate dehydrogenase (acetyl-transferring)] phosphotransferase


Proteins

Protein ID name full name