Page last updated: 2024-11-11

4-hydroxyretinoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-hydroxyretinoic acid: RN given refers to cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

all-trans-4-hydroxyretinoic acid : A retinoid that consists of all-trans-retinoic acid bearing a hydroxy substituent at position 4 on the cyclohexenyl ring. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

all-trans-4-hydroxyretinoate : A hydroxy monocarboxylic acid anion that is the conjugate base of all-trans-4-hydroxyretinoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6438629
CHEMBL ID1329343
CHEBI ID63795
CHEBI ID94464
SCHEMBL ID1718341
SCHEMBL ID1718339
MeSH IDM0071888

Synonyms (46)

Synonym
LMPR01090025
all-trans-4-hydroxyretinoic acid
SPECTRUM5_002069
NCGC00163129-01
4-hydroxyretinoic acid
66592-72-1
4-hydroxy-13-cis-retinoic acid
4-hydroxy-all-trans-retinoate
(7e,9e,11e,13e)-4-hydroxyretinoic acid
all-trans-4-hydroxyretinoate
rac all-trans 4-hydroxy retinoic acid
(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
unii-gt84hx78dr
gt84hx78dr ,
retinoic acid, 4-hydroxy-
4-hydroxy-(7e,9e,11e,13e)-retinoic acid
(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic 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
4-hydroxy-all-trans-retinoic acid
CHEBI:63795 ,
BRD-A96799240-001-01-7
CHEMBL1329343
SCHEMBL1718341
SCHEMBL1718339
retinoic acid, 4-hydroxy-, 13-cis-
CHEBI:94464
4-oh-retinoate
4-hydroxy-retinoate
4-hydroxy-13-cis-retinoate
4-oh-retinoic acid
4-hydroxy-retinoic acid
rac-4-hydroxy-all-trans-retinoate
DTXSID40867235
1346606-78-7
1346606-21-0
(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
KGUMXGDKXYTTEY-FRCNGJHJSA-N
Q27132808
rac-4-hydroxy-all-trans-retinoic acid
all-trans-4-hydroxy retinoic acid;4-hydroxy-all-trans-retinoic acid
racall-trans4-hydroxyretinoicacid-d3
rac4-hydroxy-9-cis-retinoicacid-d3
HY-125904
CS-0102989
all-trans-4-hydroxy retinoic acid
retinoic acid, 4-hydroxy-, 9-cis-

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In rats dosed with 40 mg/kg, food consumption and growth as well as liver retinol and retinyl palmitate concentrations decreased, while serum retinol and liver weight increased within 28 days following the injection."( Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection.
Garcin, H; Narbonne, JF; Spear, PA, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
retinoidOxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
secondary allylic alcoholAn allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to one other carbon and one hydrogen.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (13)

PathwayProteinsCompounds
Metabolism14961108
Biological oxidations150276
Phase I - Functionalization of compounds69175
Cytochrome P450 - arranged by substrate type30110
Vitamins415
Miscellaneous substrates315
Signaling Pathways1269117
Signaling by Nuclear Receptors15246
Signaling by Retinoic Acid2431
RA biosynthesis pathway1119
Retinol Metabolism3730
Vitamin A Deficiency3730
22q11.2 copy number variation syndrome228

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency23.26260.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency22.38720.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency6.30960.011212.4002100.0000AID1030
glucocerebrosidaseHomo sapiens (human)Potency8.91250.01268.156944.6684AID2101
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency70.79460.354828.065989.1251AID504847
survival motor neuron protein isoform dHomo sapiens (human)Potency7.94330.125912.234435.4813AID1458
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (16.67)18.7374
1990's2 (16.67)18.2507
2000's5 (41.67)29.6817
2010's1 (8.33)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.15

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.15 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]