Acitretin - Moligand™, ≥98% , Retinoid receptor agonist, CAS No.55079-83-9, Retinoid receptor agonist

CAS: 55079-83-9 Cat. No.: A102064 Molecular Weight: 326.43 EC Number: 259-474-4

GRADE & PURITY Moligand™, ≥98%

Synonyms

Acitretin | ACITRETIN [HSDB] | (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(methyloxy)phenyl]nona-2,4,6,8-tetraenoic acid | AKOS015889991 | Q341500 | Ro-10-1670 | SMR000499573 | 9-cis Acitretin | Soriatane | Neotigason | Acitretin- Bio-X | Z2312273468

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

It is a potent activator of the α-secretase ADAM10 gene expression and apoptosis inducer via the CD95 signalling pathway. It is also a systemic retinoid drug used in the treatment of severe psoriasis.

Specifications

Synonyms

Acitretin | ACITRETIN [HSDB] | (2E, 4E, 6E, 8E)-3, 7-dimethyl-9-[2, 3, 6-trimethyl-4-(methyloxy)phenyl]nona-2, 4, 6, 8-tetraenoic acid | AKOS015889991 | Q341500 | Ro-10-1670 | SMR000499573 | 9-cis Acitretin | Soriatane | Neotigason | Acitretin- Bio-X | Z2312273468

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).Synthetic, highly lipophilic retinoid. Etretinate metabolite with a shorter half-life. Increases ADAM10 gene expression. Induce

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Retinoid receptor agonist

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488195292
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195292
• Canonical Smiles: CC1=CC(=C(C(=C1C=CC(=CC=CC(=CC(=O)O)C)C)C)C)OC
• IUPAC Name: (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• InChIKey: IHUNBGSDBOWDMA-AQFIFDHZSA-N
• INCHI: 1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
• Isomeric SMILES: CC1=CC(=C(C(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
• WGK Germany: 3
• UN Number: 3077
• Molecular Weight: 326.43
• Reaxy-Rn: 15057225
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=15057225&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Retinoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Retinoids
• Alternative Parents: Sesquiterpenoids Styrenes Phenoxy compounds Methoxybenzenes Medium-chain fatty acids Anisoles Methyl-branched fatty acids Alkyl aryl ethers Unsaturated fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Retinoic acid - Retinoid skeleton - Sesquiterpenoid - Cyclofarsesane sesquiterpenoid - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Medium-chain fatty acid - Styrene - Alkyl aryl ether - Branched fatty acid - Methyl-branched fatty acid - Monocyclic benzene moiety - Fatty acyl - Fatty acid - Benzenoid - Unsaturated fatty acid - Monocarboxylic acid or derivatives - Ether - Carboxylic acid - Carboxylic acid derivative - Carbonyl group - Organooxygen compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
• External Descriptors: retinoid - alpha,beta-unsaturated monocarboxylic acid - acitretin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

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Associated Targets(non-human)

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Hamster (598 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Plasma (328 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light Sensitive；Air Sensitive；Heat Sensitive；Moisture sensitive
• Melt Point(°C): 230 °C
• Molecular Weight: 326.400 g/mol
• XLogP3: 6.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 326.188 Da
• Monoisotopic Mass: 326.188 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 539.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

References

1. Yongjie Bao, Wenni Rong, An Zhu, Yuan Chen, Huiyue Chen, Yirui Hong, Jingyang Le, Qiyao Wang, C. Benjamin Naman, Zhipeng Xu, Lin Liu, Wei Cui, Xiang Wu.  (2023)  Retinoic Acid Receptor Is a Novel Therapeutic Target for Postoperative Cognitive Dysfunction.  Pharmaceutics,  15  (9): (2311).  [PMID:37765280] [10.3390/pharmaceutics15092311]