Home Other Building Blocks 102121-60-8
102121-60-8,MFCD00673916
Catalog No.:AA0006LM
102121-60-8 | AM580
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1mg
≥98%
1 week  
$92.00   $64.00
- +
5mg
>97.0%(GC)
1 week  
$132.00   $92.00
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10mg
99%
1 week  
$193.00   $135.00
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25mg
≥98%
1 week  
$400.00   $280.00
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50mg
99%
1 week  
$638.00   $447.00
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100mg
99%
1 week  
$1,082.00   $758.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0006LM
Chemical Name:
AM580
CAS Number:
102121-60-8
Molecular Formula:
C22H25NO3
Molecular Weight:
351.4388
MDL Number:
MFCD00673916
IUPAC Name:
4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid
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)
InChI Key:
SZWKGOZKRMMLAJ-UHFFFAOYSA-N
SMILES:
O=C(c1ccc2c(c1)C(C)(C)CCC2(C)C)Nc1ccc(cc1)C(=O)O
UNII:
VZ5S5G9ZFZ
NSC Number:
608001
Properties
Computed Properties
 
Complexity:
546  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
351.183g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
351.446g/mol
Monoisotopic Mass:
351.183g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
66.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.4  

Synonyms
 
Am 580 
AM-580 
CD-336 
C15619 
J-000631 
SR-01000597463-1 
SR-01000597463-3 
BRD-K06854232-001-02-5 
4-[(1,1,4,4-tetramethyltetralin-6-carbonyl)amino]benzoic acid 
4-(((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl)amino)benzoic acid 
4-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-7-carboxamido)benzoic acid 
4-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydronaphthalene-2-Carbox Amido)Benzoic Acid 
4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid 
Ro 40-6055 
4-[(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoic acid 
4-[(5,5,8,8-tetramethyl6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid 
Benzoic acid,5',8',8'-tetramethyl-5',6',7',8'-tetrahydro-2'- naphthyl)amino)-: 
Benzoic acid, 4((5',5',8',8'-tetramethyl-5',6',7', 8'-tetrahydro-2'- naphthyl)amino)-: 
Benzoic acid, 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]- 
EQN 
D0RD0R 
C22H25NO3 
CID2126 
AR-1G0023 
CD 336 
C22-H25-N-O3 
B4654 
A11792 
C068073 
102613-10-5 
UNII-VZ5S5G9ZFZ 
4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid 
Ro-40-6055 
4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamido)benzoic acid 
VZ5S5G9ZFZ 
BRN 3565084 
CHEMBL69367 
Am580 
CHEBI:64210 
MFCD00673916 
NSC608001 
Benzoic acid,4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]- 
4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl)aminobenzoic acid 
4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid 
4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid 
Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl)amino- 
SR-01000597463 
SZWKGOZKRMMLAJ-UHFFFAOYSA-N 
CD-336 
Ro406055 
ACMC-20cewx 
Tocris-0760 
AC1Q5TXH 
Spectrum5_001941 
AC1L1CZ6 
DSSTox_CID_20758 
DSSTox_RID_79590 
CBiol_001850 
DSSTox_GSID_40758 
Ro 40-6055 
BSPBio_001527 
KBioGR_000247 
KBioSS_000247 
SCHEMBL726740 
BML2-E09 
GTPL2647 
DTXSID5040758 
CTK4A0696 
KBio2_000247 
KBio2_002815 
Ro-40-6055 
KBio2_005383 
KBio3_000493 
KBio3_000494 
AOB5264 
EX-A843 
BCPP000411 
Bio1_000136 
Bio1_000625 
Bio1_001114 
Bio2_000247 
AM580 
Bio2_000727 
HMS1361M09 
HMS1791M09 
HMS1989M09 
HMS3266B10 
HMS3402M09 
HMS3675H13 
BCP03051 
KS-00000PC3 
ZINC3784077 
102121-60-8 
Tox21_300780 
3437AH 
BDBM50052414 
BN0066 
AKOS024458635 
API0008429 
BCP9000281 
CS-3251 
NSC-608001 
4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acid 
Am 580 
IDI1_033997 
NCGC00024774-01 
NCGC00024774-02 
NCGC00024774-03 
NCGC00024774-04 
NCGC00024774-05 
NCGC00024774-06 
NCGC00024774-07 
NCGC00254684-01 
4CA-0061 
AM-580 
AK206372 
AM580, >=98% (HPLC) 
AS-16835 
HY-10475 
LS-38310 
NCI60_004717 
BCP0726000221 
RT-011258 
CAS-102121-60-8 
FT-0738259 
Literature

Title: Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.

Journal: Scientific reports 20140101

Title: Roflumilast enhances the renal protective effects of retinoids in an HIV-1 transgenic mouse model of rapidly progressive renal failure.

Journal: Kidney international 20120501

Title: Can we cure HIV-1-associated nephropathy in transgenic mice?

Journal: Kidney international 20120501

Title: Retinoic acid receptor agonists regulate expression of ATP-binding cassette transporter G1 in macrophages.

Journal: Biochimica et biophysica acta 20120401

Title: Rapid and efficient reprogramming of somatic cells to induced pluripotent stem cells by retinoic acid receptor gamma and liver receptor homolog 1.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20111108

Title: Effect of synthetic ligands of PPAR α, β/δ, γ, RAR, RXR and LXR on the fatty acid composition of phospholipids in mice.

Journal: Lipids 20111101

Title: Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.

Journal: Environmental health perspectives 20110801

Title: Neuregulins are essential for spermatogonial proliferation and meiotic initiation in neonatal mouse testis.

Journal: Development (Cambridge, England) 20110801

Title: Retinoic acid inhibits endometrial cancer cell growth via multiple genomic mechanisms.

Journal: Journal of molecular endocrinology 20110401

Title: Role of the retinoic acid receptor-α in HIV-associated nephropathy.

Journal: Kidney international 20110301

Title: Identification of diaryl ether-based ligands for estrogen-related receptor α as potential antidiabetic agents.

Journal: Journal of medicinal chemistry 20110210

Title: Novel retinoic acid receptor alpha agonists for treatment of kidney disease.

Journal: PloS one 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Research resource: transcriptome profiling of genes regulated by RXR and its permissive and nonpermissive partners in differentiating monocyte-derived dendritic cells.

Journal: Molecular endocrinology (Baltimore, Md.) 20101101

Title: Retinoic acid receptor-α signalling antagonizes both intracellular and extracellular amyloid-β production and prevents neuronal cell death caused by amyloid-β.

Journal: The European journal of neuroscience 20101001

Title: Allele-specific down-regulation of RPTOR expression induced by retinoids contributes to climate adaptations.

Journal: PLoS genetics 20101001

Title: All-trans retinoic acid enhances the transport of phase II metabolites of benzo[a]pyrene by inducing the Breast Cancer Resistance Protein expression in Caco-2 cells.

Journal: Toxicology letters 20100816

Title: Keratins 2 and 4/13 in reconstituted human skin are reciprocally regulated by retinoids binding to nuclear receptor RARalpha.

Journal: Experimental dermatology 20100701

Title: Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARalpha agonist AM580.

Journal: Oncogene 20100624

Title: Acidic retinoids synergize with vitamin A to enhance retinol uptake and STRA6, LRAT, and CYP26B1 expression in neonatal lung.

Journal: Journal of lipid research 20100201

Title: Synthesis and pharmacological characterization of Disila-AM80 (Disila-tamibarotene) and Disila-AM580, silicon analogues of the RARalpha-selective retinoid agonists AM80 (Tamibarotene) and AM580.

Journal: ChemMedChem 20091101

Title: Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands.

Journal: Journal of medicinal chemistry 20090326

Title: Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.

Journal: Bioorganic & medicinal chemistry letters 20090115

Title: Experimental effect of retinoic acids on apoptosis during the development of diabetic retinopathy.

Journal: Clinical ophthalmology (Auckland, N.Z.) 20080301

Title: Expression of retinoic acid receptors in human endometrial carcinoma.

Journal: Cancer science 20080201

Title: The Retinoic Acid Receptor-alpha mediates human T-cell activation and Th2 cytokine and chemokine production.

Journal: BMC immunology 20080101

Title: Galactomutarotase and other galactose-related genes are rapidly induced by retinoic acid in human myeloid cells.

Journal: Biochemistry 20071225

Title: Apoptotic extinction of germ cells in testes of Cyp26b1 knockout mice.

Journal: Endocrinology 20071001

Title: A widely used retinoic acid receptor antagonist induces peroxisome proliferator-activated receptor-gamma activity.

Journal: Molecular pharmacology 20070501

Title: Inhibitory effects of retinoic acid receptor alpha stimulants on murine cataractogenesis through suppression of deregulated calpains.

Journal: Investigative ophthalmology & visual science 20070501

Title: Retinoic acid regulates CD1d gene expression at the transcriptional level in human and rodent monocytic cells.

Journal: Experimental biology and medicine (Maywood, N.J.) 20070401

Title: Cellular retinoic acid bioavailability determines epithelial integrity: Role of retinoic acid receptor alpha agonists in colitis.

Journal: Molecular pharmacology 20070101

Title: PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells.

Journal: The Journal of experimental medicine 20061002

Title: Epigenetic silencing of occludin promotes tumorigenic and metastatic properties of cancer cells via modulations of unique sets of apoptosis-associated genes.

Journal: Cancer research 20060915

Title: Retinoic acid improves a hybridoma culture in a fructose-based medium by up-regulation of fructose incorporation via retinoid nuclear receptors.

Journal: Bioscience, biotechnology, and biochemistry 20060901

Title: Retinoic acid exerts dual regulatory actions on the expression and nuclear localization of interferon regulatory factor-1.

Journal: Experimental biology and medicine (Maywood, N.J.) 20060501

Title: Retinoic acid-induced CD38 expression in HL-60 myeloblastic leukemia cells regulates cell differentiation or viability depending on expression levels.

Journal: Journal of cellular biochemistry 20060415

Title: Retinoic acid induces p27Kip1 nuclear accumulation by modulating its phosphorylation.

Journal: Cancer research 20060415

Title: Telomerase targeting by retinoids in cells from patients with myeloid leukemias of various subtypes, not only APL.

Journal: Leukemia 20060401

Title: Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.

Journal: Journal of cellular biochemistry 20060201

Title: Retinoic acid amplifies the host immune response to LPS through increased T lymphocytes number and LPS binding protein expression.

Journal: Molecular and cellular endocrinology 20051221

Title: Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist.

Journal: Journal of medicinal chemistry 20051201

Title: Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells.

Journal: Journal of periodontal research 20051201

Title: Physiological and receptor-selective retinoids modulate interferon gamma signaling by increasing the expression, nuclear localization, and functional activity of interferon regulatory factor-1.

Journal: The Journal of biological chemistry 20051028

Title: Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.

Journal: Molecular endocrinology (Baltimore, Md.) 20051001

Title: Expression of the retinoic acid-metabolizing enzyme CYP26A1 limits programmed cell death.

Journal: Molecular pharmacology 20050501

Title: Implication of Wt1 in the pathogenesis of nephrogenic failure in a mouse model of retinoic acid-induced caudal regression syndrome.

Journal: The American journal of pathology 20050501

Title: A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation.

Journal: Molecular pharmacology 20041201

Title: Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands.

Journal: Archives of toxicology 20041101

Title: Survival of activated human T lymphocytes is promoted by retinoic acid via induction of IL-2.

Journal: International immunology 20040301

Title: Modifying effects of 1'-acetoxychavicol acetate (ACA) and the novel synthetic retinoids Re-80, Am-580 and Am-55P in a two-stage carcinogenesis model in female rats.

Journal: Toxicologic pathology 20040101

Title: All-trans retinoic acid modulates microvascular endothelial cell hemostatic properties.

Journal: Haematologica 20030801

Title: Ligation of retinoic acid receptor alpha regulates negative selection of thymocytes by inhibiting both DNA binding of nur77 and synthesis of bim.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030401

Title: Arginine of retinoic acid receptor beta which coordinates with the carboxyl group of retinoic acid functions independent of the amino acid residues responsible for retinoic acid receptor subtype ligand specificity.

Journal: Archives of biochemistry and biophysics 20030115

Title: RAR agonists stimulate SOX9 gene expression in breast cancer cell lines: evidence for a role in retinoid-mediated growth inhibition.

Journal: Oncogene 20021107

Title: Synthesis and biological activity of retinoic acid receptor-alpha specific amides.

Journal: Bioorganic & medicinal chemistry letters 20021104

Title: Enhancement of the inducible NO synthase activation by retinoic acid is mimicked by RARalpha agonist in vivo.

Journal: American journal of physiology. Endocrinology and metabolism 20020901

Title: Effects of retinoic acid receptor-selective agonists on human nasal epithelial cell differentiation.

Journal: American journal of respiratory cell and molecular biology 20011201

Title: Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.

Journal: Biochimica et biophysica acta 20011031

Title: Retinoids inhibit the actions of angiotensin II on vascular smooth muscle cells.

Journal: Circulation research 20010330

Title: Synergistic teratogenic effects induced by retinoids in mice by coadministration of a RARalpha- or RARgamma-selective agonist with a RXR-selective agonist.

Journal: Toxicology and applied pharmacology 20010101

Title: Effects of retinoids on in vitro and in vivo IgE production.

Journal: International archives of allergy and immunology 20010101

Title: In silico discovery of novel retinoic acid receptor agonist structures.

Journal: BMC structural biology 20010101

Title: Induction of the cytochrome P450 gene CYP26 during mucous cell differentiation of normal human tracheobronchial epithelial cells.

Journal: Molecular pharmacology 20000901

Title: Retinoic acid is a negative regulator for the differentiation of cord blood-derived human mast cell progenitors.

Journal: Blood 20000501

Title: The role of specific retinoid receptors in sebocyte growth and differentiation in culture.

Journal: The Journal of investigative dermatology 20000201

Title: Evidence for the involvement of both retinoic acid receptor- and retinoic X receptor-dependent signaling pathways in the induction of tissue transglutaminase and apoptosis in the human myeloma cell line RPMI 8226.

Journal: Blood 19980401

Title: Selective high affinity retinoic acid receptor alpha or beta-gamma ligands.

Journal: Molecular pharmacology 19911001

Title: Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.

Journal: Journal of medicinal chemistry 19881101

Title: New benzoic acid derivatives with retinoid activity: lack of direct correlation between biological activity and binding to cellular retinoic acid binding protein.

Journal: Cancer research 19870701

Title: Purification and properties of polyol dehydrogenase from Cephalosporium chrysogenus.

Journal: Journal of bacteriology 19760101

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