Skip to main content

MW 351.4 Da, Purity >98%. Selective RARα agonists (EC50 values are 0.3, 8.6 and 13 nM for RARα, RARβ and RARγ respectively). Shows anticancer effect. Active in vivo..

Be the first to review this product! Submit a review

Images

Chemical Structure - AM580, RARalpha agonists (AB141314), expandable thumbnail

Key facts

CAS number
102121-60-8
Purity
> 98%
Form
Solid
Molecular weight
351.4 Da
Molecular formula
C22H25NO3
PubChem identifier
2126
Nature
Synthetic

Target data

Alternative names

1 25 dihydroxyvitamin D3 receptor, 25-dihydroxyvitamin D3 receptor, AIS, ANDR_HUMAN, AR, AR8, Androgen nuclear receptor variant 2, Androgen receptor, Androgen receptor (dihydrotestosterone receptor; testicular feminization; spinal and bulbar muscular atrophy; Kennedy disease), Atherosclerosis, susceptibility to, included, BAR, Bile acid receptor, CHNG1, DHTR, DKFZp686N23123, Dihydro testosterone receptor, Dihydrotestosterone receptor (DHTR), ER, ER-alpha, ER-beta, ER[a], ER[b], ESR, ESR B, ESR BETA, ESR1_HUMAN, ESRA, ESTR B, Era, Erb, Erb2, Estr, Estra, Estradiol Receptor alpha, Estradiol Receptor beta, Estradiol receptor, Estrogen Receptor 1, Estrogen Receptor 2, Estrogen receptor, Estrogen receptor 1 (alpha), Estrogen receptor 2 (ER beta), Estrogen receptor 2 ER beta, Estrogen receptor alpha, Estrogen receptor beta 4, Estrogen resistance, included, FLJ00280, FLJ00318, FLJ16020, FLJ16733, Farnesoid X-activated receptor, Farnesol receptor HRR-1, HAP, HBV-activated protein, HDL cholesterol, augmented response of, to hormone replacement, included, HRR 1, HUMARA, HYSP1, IMD42, KD, Kennedy disease (KD), LGR 3, MGC102720, MGC129539, MGC75129, Member 1, Myocardial infarction, susceptibility to, included, NF-E2-related factor 2, NF2L2_HUMAN, NR1B1, NR1B2, NR1B3, NR1F3, NR1I1, NR2B1, NR3A1, NR3A2, NR3C4, NRF2, Nfe2l2, Nuclear factor, Nuclear factor (erythroid derived 2) like 2, Nuclear factor erythroid 2-related factor 2, Nuclear factor erythroid derived 2 like 2, Nuclear mitotic apparatus protein retinoic acid receptor alpha fusion protein, Nuclear receptor ROR-gamma, Nuclear receptor RZR-gamma, Nuclear receptor subfamily 1 group B member 1, Nuclear receptor subfamily 1 group B member 2, Nuclear receptor subfamily 1 group B member 3, Nuclear receptor subfamily 1 group F member 3, Nuclear receptor subfamily 1 group I member 1, Nuclear receptor subfamily 2 group B member 1, Nuclear receptor subfamily 3 group A member 1, Nuclear receptor subfamily 3 group A member 2, Nuclear receptor subfamily 3 group C member 4, Nuclear receptor subfamily 3 group C member 4 (NR3C4), Nucleophosmin retinoic acid receptor alpha fusion protein NPM RAR long form, OTTHUMP00000017718, OTTHUMP00000017719, OTTHUMP00000022510, PPP1R163, Protein phosphatase 1, regulatory subunit 163, RAR, RAR related orphan nuclear receptor variant 2, RAR related orphan receptor C, isoform a, RAR related orphan receptor gamma, RAR-alpha, RAR-beta, RAR-epsilon, RAR-gamma, RAR-related orphan receptor C, RARA_HUMAN, RARB_HUMAN, RARC, RARG_HUMAN, RARalpha1, RIP 14, RNESTROR, RORG_HUMAN, RRB2, RXR alpha1, RXR-interacting protein 14, RXRA_HUMAN, RZR GAMMA, RZRG, Retinoic acid binding receptor gamma, Retinoic acid nuclear receptor alpha variant 1, Retinoic acid nuclear receptor alpha variant 2, Retinoic acid receptor RXR-alpha, Retinoic acid receptor alpha, Retinoic acid receptor alpha polypeptide, Retinoic acid receptor beta, Retinoic acid receptor beta 2, Retinoic acid receptor beta 4, Retinoic acid receptor beta 5, Retinoic acid receptor beta polypeptide, Retinoic acid receptor gamma 2, Retinoic acid receptor, gamma, Retinoid X nuclear receptor alpha, Retinoid X receptor alpha, Retinoid X receptor-interacting protein 14, Retinoid-related orphan receptor-gamma, Rorc, SBMA, SMAX1, Seven transmembrane helix receptor, Spinal and bulbar muscular atrophy, Spinal and bulbar muscular atrophy (SBMA), TFM, TOR, TSH Receptor, TSHR_HUMAN, Testicular Feminization (TFM), Thyroid adenoma hyperfunctioning, Thyroid carcinoma with thyrotoxicosis, Thyroid stimulating hormone receptor, isoform 2, Thyroid-stimulating hormone receptor, Thyrotropin receptor, Thyrotropin receptor I, Thyrotropin receptor I, hTSHR I, VDR_HUMAN, Vitamin D (1,25- dihydroxyvitamin D3) receptor, Vitamin D hormone receptor, Vitamin D nuclear receptor variant 1, Vitamin D receptor, Vitamin D3 receptor, androgen receptor splice variant 4b, erythroid derived 2, hTSHR I, like 2, nuclear factor erythroid 2 like 2

Recommended products

MW 351.4 Da, Purity >98%. Selective RARα agonists (EC50 values are 0.3, 8.6 and 13 nM for RARα, RARβ and RARγ respectively). Shows anticancer effect. Active in vivo..

Key facts

Purity
> 98%
PubChem identifier
2126
Solubility

Soluble in DMSO to 100 mM.

Soluble in ethanol to 50 mM.

Biochemical name
4-{[(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid
Biological description

Selective RARα agonists (EC50 values are 0.3, 8.6 and 13 nM for RARα, RARβ and RARγ respectively). Shows anticancer effect. Active in vivo.

Canonical SMILES
CC1(CCC(C2=C1C=CC(=C2)C(=O)NC3=CC=C(C=C3)C(=O)O)(C)C)C
InChI
InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChIKey
SZWKGOZKRMMLAJ-UHFFFAOYSA-N
IUPAC name
4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions, The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

Retinoic Acid Receptor gamma (RARG) Vitamin D Receptor (VDR) and Estrogen Receptor (ER) are members of the nuclear receptor superfamily acting as transcription factors regulating gene expression. Known by other names these receptors are pivotal in various physiological functions. RARG's molecular mass is approximately 54 kDa while others such as VDR weigh around 48 kDa. These receptors show diverse expression patterns; RARG is found in the skin and immune cells VDR expresses in bones and intestines and ER is notably present in breast tissue. TSH Receptor (TSH-R) operates in thyroid gland while Androgen Receptor (AR) finds expression mostly in prostate tissue. Retinoic Acid Receptor alpha (RARA) and beta (RARB) share similar functional roles with RXRA but each has unique tissue-specific patterns of expression. ROR gamma and Nrf2 also play key roles as transcriptional regulators in immune and oxidative stress responses respectively.

Biological function summary

These nuclear receptors influence major body systems by interacting with hormones or vitamins to regulate gene transcription. They form dimeric or heterodimeric complexes such as RXRA pairing with retinoic acid receptors. RARG VDR and ER modulate cell differentiation proliferation and apoptosis. TSH-R primarily regulates thyroid hormone synthesis influencing metabolism. AR mediates sexual development and reproductive functions while RORA and RARB partakes in embryonic development. ROR gamma is essential for thymopoiesis an aspect of immune defense. Nrf2 manages cellular antioxidant defense by initiating transcription of protective genes promoting cellular resilience against oxidative stress.

Pathways

These receptors integrate into critical signaling networks affecting multiple cellular processes. The retinoic acid-mediated pathway involves RARG RARA and RXRA influencing gene expression for tissue morphogenesis and homeostasis often linked with RXRA partners like PPARs. Similarly the Vitamin D pathway involves VDR impacting calcium and phosphate metabolism through interaction with proteins like calmodulin. Their involvement extends to immune response regulation and metabolic processes wherein ER components intersect with steroid biosynthesis pathways to modulate reproductive health.

Associated diseases and disorders

The misregulation of these receptors links to various clinical conditions. RAR malfunctions can result in dermatological disorders and immune diseases. Increased or decreased activity in AR associates with prostate cancer affirming its role in tumorigenesis. RXRA in metabolic syndrome has links with lipid regulation issues when pathways malfunction. VDR's defective signaling connects to osteoporosis through impaired calcium metabolism. Nrf2's defective regulation associates with neurodegenerative diseases and cancer driven by disrupted oxidative stress responses.

Product promise

We are dedicated to supporting your work with high quality reagents and we are here for you every step of the way should you need us.

In the unlikely event of one of our products not working as expected, you are covered by our product promise.

Full details and terms and conditions can be found here:
Terms & Conditions.

1 product image

  • Chemical Structure - AM580, RARalpha agonists (ab141314), expandable thumbnail

    Chemical Structure - AM580, RARalpha agonists (ab141314)

    2D chemical structure image of ab141314, AM580, RARalpha agonists

Downloads

Product protocols

For this product, it's our understanding that no specific protocols are required. You can:

Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.

For licensing inquiries, please contact partnerships@abcam.com