Classification Term: 168611

Retinoids [PR0109] (ontology term: d9aa10b14fec20093f248cc2b93473ec)

Retinoids [PR0109]

found 76 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Isoprenoids [PR01]

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

all-trans-Retinoic acid

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

C20H28O2 (300.2089188)


all-trans-Retinoic acid is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID:17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [HMDB] L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XF - Retinoids for cancer treatment D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use > D10AD - Retinoids for topical use in acne C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent Acquisition and generation of the data is financially supported in part by CREST/JST. C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D003879 - Dermatologic Agents > D007641 - Keratolytic Agents D000970 - Antineoplastic Agents Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.

   

Retinal

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

C20H28O (284.2140038)


A carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. [HMDB]. Retinal is found in many foods, some of which are flaxseed, pepper (c. baccatum), climbing bean, and other soy product. Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids CONFIDENCE standard compound; INTERNAL_ID 142

   

All-trans-13,14-dihydroretinol

(4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-4,6,8-trien-1-ol

C20H32O (288.24530219999997)


All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG) [HMDB] All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

Retinoyl b-glucuronide

1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-β-D-glucopyranuronic acid O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid

C26H36O8 (476.2410056)


Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers. [HMDB] Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

4-Hydroxyretinoic acid

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid

C20H28O3 (316.2038338)


4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384) [HMDB] 4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

4-Ketoretinoic acid

all-trans-4-Oxoretinoic acid

C20H26O3 (314.1881846)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

   

all-trans-5,6-Epoxyretinoic acid

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

C20H28O3 (316.2038338)


all-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxy-atRA, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-5,6-Epoxyretinoic acid is considered to be a practically insoluble (in water) and a weak acidic compound. all-trans-5,6-Epoxyretinoic acid is an isoprenoid lipid molecule. all-trans-5,6-Epoxyretinoic acid can be found primarily in human kidney and liver tissues; and in blood and urine. Within a cell, all-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm, in the extracellular space, or near the membrane. A human metabolite taken as a putative food compound of mammalian origin [HMDB] D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

9-cis-Retinoic acid

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

C20H28O2 (300.2089188)


9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228). Isolated from pancreas of pig and cow. Digestive enzyme. It is used in replacement therapy. It is used to prepare protein hydrolysates for pre- and post-operative diets D - Dermatologicals > D11 - Other dermatological preparations > D11A - Other dermatological preparations > D11AH - Agents for dermatitis, excluding corticosteroids L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XF - Retinoids for cancer treatment C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D000970 - Antineoplastic Agents D003879 - Dermatologic Agents Same as: D02815

   

9-cis-Retinol

(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

C20H30O (286.229653)


9-cis-retinol is a retinoid. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228). Constituent of cod liver oil

   

9-cis-Retinal

(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

C20H28O (284.2140038)


In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID:15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of. unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID:10893430), in maintaining normal reproduction, and in the immune response (PMID:8882153). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID:10322133). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID:10418975), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID:8825126, PMID:12743994). In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID: 15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

all-trans-18-Hydroxyretinoic acid

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

C20H28O3 (316.2038338)


A retinoid that consists of all-trans-retinoic acid bearing an hydroxy substituent at position 18.

   

(3S)-all-trans-3-hydroxyretinal

(2E,4E,6E,8E)-9-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal (3S)-all-trans-3-hydroxyretinal

C20H28O2 (300.2089188)


   

11-cis-Dehydroretinal

11-cis-3-Dehydroretinal

C20H26O (282.1983546)


   

(3S)-11-cis-3-hydroxyretinal

(2E,4Z,6E,8E)-9-[(4S)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal (3S)-11-cis-3-hydroxyretinal

C20H28O2 (300.2089188)


   

4-oxo-Retinoic acid

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

C20H26O3 (314.1881846)


4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545) [HMDB] 4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

   

all-trans-18-Hydroxyretinoic acid

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

C20H28O3 (316.2038338)


all-trans-18-Hydroxyretinoic acid, also known as 18-hydroxyretinoic acid, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-18-Hydroxyretinoic acid is considered to be a practically insoluble (in water) and a weakly acidic compound. all-trans-18-Hydroxyretinoic acid is an isoprenoid lipid molecule. Within a cell, all-trans-18-hydroxyretinoic acid is primarily located in the extracellular space and near the membrane. 18-Hydroxyretinoic acid is a metabolite of tretinoin. Tretinoin is the acid form of vitamin A and is also known as all-trans retinoic acid or ATRA. It is a drug commonly used to treat acne vulgaris and keratosis pilaris. It is available as a cream or gel (brand names Aberela, Airol, Renova, Atralin, Retin-A, Avita, Retacnyl, Refissa, or Stieva-A). It is also used to treat acute promyelocytic leukemia (APL) and is sold for this indication by Roche under the brand name Vesanoid. It is also available as a generic. (Wikipedia) A human metabolite taken as a putative food compound of mammalian origin [HMDB]

   

Tretinoin

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

C20H28O2 (300.2089188)


L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XF - Retinoids for cancer treatment D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use > D10AD - Retinoids for topical use in acne C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D003879 - Dermatologic Agents > D007641 - Keratolytic Agents D000970 - Antineoplastic Agents CONFIDENCE standard compound; INTERNAL_ID 135 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.574 Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.

   

Etretinate

(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester

C23H30O3 (354.21948299999997)


D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BB - Retinoids for treatment of psoriasis C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D003879 - Dermatologic Agents > D007641 - Keratolytic Agents

   

3,4-didehydro-retinol

All-Trans-3,4-Didehydro Retinol

C20H28O (284.2140038)


   

11Z-3,4-didehydro-retinol

11-cis-3,4-didehydroretinol

C20H28O (284.2140038)


   

Retinyl acetate

Retinol Acetate/All-trans-retinyl Acetate

C22H32O2 (328.24021719999996)


C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents D007155 - Immunologic Factors Retinyl acetate is a synthetic acetate ester form derived from retinol and has potential antineoplastic and chemo preventive activities.

   

all-trans-retinyl stearate

(2E,4E,6E,8E)-Octadecanoic acid3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester

C38H64O2 (552.4906043999999)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

all-trans-retinyl oleate

(2E,4E,6E,8E)-Octadec-9-enoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester

C38H62O2 (550.4749552)


   

all-trans-retinyl linolate

(2E,4E,6E,8E)-Octadeca-9,12,15-enoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)- nona-2, 4,6,8,tetraenyl ester

C38H58O2 (546.4436568)


   

13-cis-retinal

Retinal, 13-cis-

C20H28O (284.2140038)


A retinal in which the double bond alpha- to the aldehyde group has cis configuration, whilst the remaining acyclic double bonds have trans configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

All-Trans-3,4-Didehydro-Retinoic acid

All-Trans-3,4-Didehydro-Retinoic acid

C20H26O2 (298.1932696)


   

9,13-di-cis-retinoic acid

9,13-di-cis-retinoic acid

C20H28O2 (300.2089188)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

11-cis-Retinoic acid

11-cis-Retinoic acid

C20H28O2 (300.2089188)


The 11-cis-isomer of retinoic acid.

   

DACP analog of retinoic acid

DACP analog of retinoic acid

C20H26O3 (314.1881846)


   

19-Hydroxy-13-cis-retinoic acid

19-Hydroxy-13-cis-retinoic acid

C20H28O3 (316.2038338)


   

19-Oxo-all-trans-retinoic acid

19-Oxo-all-trans-retinoic acid

C20H26O3 (314.1881846)


   

19-Oxo-9-cis-retinoic acid

19-Oxo-9-cis-retinoic acid

C20H26O3 (314.1881846)


   

20,14-retro-retinoic acid

20,14-retro-retinoic acid

C20H28O2 (300.2089188)


   

14-methyl-20,14-retro-retinoic acid

14-methyl-20,14-retro-retinoic acid

C21H30O2 (314.224568)


   

14-methyl-all-trans-retinoic acid

14-methyl-all-trans-retinoic acid

C21H30O2 (314.224568)


   

8-18 bonded retinal

8-18 bonded retinal

C20H26O (282.1983546)


   

6-s-cis-locked retinal

6-s-cis-locked retinal

C20H26O (282.1983546)


   

11-cis- and 12s-trans-fixed retinal

11-cis- and 12s-trans-fixed retinal

C20H26O (282.1983546)


   

11Z-6s-cis-fixed bicyclic retinal

11Z-6s-cis-fixed bicyclic retinal

C20H26O (282.1983546)


   

11Z-6s-trans-fixed bicyclic retinal

11Z-6s-trans-fixed bicyclic retinal

C20H26O (282.1983546)


   

(11Z)-8,18-ethanoretinal

(11Z)-8,18-ethanoretinal

C22H30O (310.229653)


   

(11Z)-8,18-methano-retinal

(11Z)-8,18-methano-retinal

C21H28O (296.2140038)


   
   

(2E,4E,6Z)-7-(7,7-Dimethyl-4,5,6,7-tetrahydro-1H-inden-2-yl)-3-methyl-octa-2,4,6-trienal

(2E,4E,6Z)-7-(7,7-Dimethyl-4,5,6,7-tetrahydro-1H-inden-2-yl)-3-methyl-octa-2,4,6-trienal

C20H26O (282.1983546)


   

(3R)-all-trans-3-hydroxyretinal

(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal (3R)-all-trans-3-hydroxyretinal

C20H28O2 (300.2089188)


   

Retinol

Vitamin A

C20H30O (286.229653)


A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified). D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use > D10AD - Retinoids for topical use in acne A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

11-cis-retinal

11-cis-retinal

C20H28O (284.2140038)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids A retinal having 2E,4Z,6E,8E-double bond geometry.

   

11Z-retinol

11-cis-Retinol

C20H30O (286.229653)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins

   

all-trans-Dehydroretinal

all-trans-Dehydroretinal

C20H26O (282.1983546)


   

13Z-retinol

13-cis-retinol

C20H30O (286.229653)


COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

all-trans-retinyl Palmitate

(2E,4E,6E,8E)-Hexadecanoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester

C36H60O2 (524.459306)


An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.

   

13-cis-retinoic acid,Isotretinoin

13-cis-retinoic acid,Isotretinoin

C20H28O2 (300.2089188)


   

19-Hydroxy-all-trans-retinoic acid

19-Hydroxy-all-trans-retinoic acid

C20H28O3 (316.2038338)


   

11-cis retro-gamma-retinal

11-cis retro-gamma-retinal

C20H28O (284.2140038)


   

9-cis retro-gamma-retinal

9-cis retro-gamma-retinal

C20H28O (284.2140038)


   

11-cis-retinyl palmitate

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2E,4Z,6E,8E-tetraen-1-yl hexadecanoate

C36H60O2 (524.459306)


The 11-cis-isomer of retinyl palmitate.

   

9-cis-4-hydroxyretinoic acid

9-cis-4-hydroxyretinoic acid

C20H28O3 (316.2038338)


   

A2-E

N-Retinylidene-N-retinylethanolamine

C42H58NO+ (592.4518158)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

isoA2E

N-Retinylidene-N-iso-retinylethanolamine

C42H58NO (592.4518158)


   

Vitamin A3

15-Apo-beta-caroten-3,15-diol

C20H30O2 (302.224568)


   

Apo-13-fucoxanthinone

(3S,5R,6R)-3-ethanoyloxy-5-hydroxy-6,7-didehydro-5,6-dihydro-13-apo-beta-caroten-13-al

C20H28O4 (332.19874880000003)


   

4-Oxoretinol

4-oxo-15-apo-beta-caroten-15-ol

C20H28O2 (300.2089188)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

(11Z)-3R-Hydroxyretinal

(11Z,3R)-3-Hydroxy-15-apo-beta-caroten-15-al

C20H28O2 (300.2089188)


   

4-Oxoretinal

4-oxo-15-apo-beta-caroten-15-al

C20H26O2 (298.1932696)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

9-cis-13,14-dihydroretinoic acid

9-cis-13,14-dihydroretinoic acid

C20H30O2 (302.224568)


   

13,14-dihydroretinoic acid

13,14-dihydroretinoic acid

C20H30O2 (302.224568)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

13,14-dihydroretinal

13,14-dihydroretinal

C20H30O (286.229653)


   

4-oxo-13,14-dihydroretinoic acid

4-oxo-13,14-dihydroretinoic acid

C20H28O3 (316.2038338)


   

Alitretinoin

9-cis-retinoic acid

C20H28O2 (300.2089188)


D - Dermatologicals > D11 - Other dermatological preparations > D11A - Other dermatological preparations > D11AH - Agents for dermatitis, excluding corticosteroids L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XF - Retinoids for cancer treatment C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D000970 - Antineoplastic Agents D003879 - Dermatologic Agents Same as: D02815 9-cis-retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as ligand for two classes of ligand-dependent transcription factors, the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228) [HMDB]

   

13,14-dihydroretinol

all-trans-13,14-dihydroretinol

C20H32O (288.24530219999997)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

9-cis-Retinal

9-cis-Retinal

C20H28O (284.2140038)


A retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

9Z-retinol

9-cis-retinol

C20H30O (286.229653)


A retinol in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.

   

4-Hydroxyretinoic acid

all-trans-4-hydroxyretinoic acid

C20H28O3 (316.2038338)


A retinoid that consists of all-trans-retinoic acid bearing a hydroxy substituent at position 4 on the cyclohexenyl ring. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

all-trans-4-Oxoretinoic acid

all-trans-4-Oxoretinoic acid

C20H26O3 (314.1881846)


A retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

   

5,6-Epoxyretinoic acid

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

C20H28O3 (316.2038338)


A retinoid obtained by epoxidation across the 5,6-double bond of retinoic acid. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

Retinoyl glucuronide

1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-beta-D-glucopyranuronic acid O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid

C26H36O8 (476.2410056)


A retinoid that is retinoic acid in which the carboxy proton has been replaced by a beta-D-glucuronyl residue.