Peretinoin - Moligand™, ≥97% , CAS No.81485-25-8

CAS: 81485-25-8 Cat. No.: P646343 Molecular Weight: 302.45 EC Number: 632-866-6

GRADE & PURITY Moligand™, ≥97%

Synonyms

E 5166 | HY-100008 | PERETINOIN [WHO-DD] | D06406 | NIK333 | NIK-333 | DTXSID801316826 | Peretinoin (JAN) | NCGC00522288-01 | 4,5-Didehydrogeranyl geranoic acid, ACR | Acyclic retinoid | Peretinoin [INN] | (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,

Storage

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

Shipped In

Ice chest + Ice pads

Overview

Peretinoin is an oral acyclic retinoid with a vitamin A-like structure that targets retinoid nuclear receptors such as retinoid X receptor (RXR) and retinoic acid receptor (RAR). Peretinoin reduces the mRNA level of sphingosine kinase 1 (SPHK1) in vitro by downregulating a transcription factor, Sp1. Peretinoin prevents the progression of non-alcoholic steatohepatitis (NASH) and the development of hepatocellular carcinoma (HCC) through activating the autophagy pathway by increased Atg16L1 expression. Peretinoin inhibits HCV RNA amplification and virus release by altering lipid metabolism with a EC50 of 9 μM.

Specifications

Synonyms

E 5166 | HY-100008 | PERETINOIN [WHO-DD] | D06406 | NIK333 | NIK-333 | DTXSID801316826 | Peretinoin (JAN) | NCGC00522288-01 | 4, 5-Didehydrogeranyl geranoic acid, ACR | Acyclic retinoid | Peretinoin [INN] | (2E, 4E, 6E, 10E)-3, 7, 11, 15-tetramethylhexadeca-2, 4,

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

Peretinoin is an active synthetic acyclic retinoid (ACR) whose in vivo anti-hepatocellular carcinoma (HCC) efficacy is attributed to its upregulatory activity toward retinoid nuclear receptors (RARbeta & RXRalpha), as well as negative regulation against s

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

INHIBITOR

Purity

≥97%

Names and Identifiers

• Canonical Smiles: CC(=CCCC(=CCCC(=CC=CC(=CC(=O)O)C)C)C)C
• IUPAC Name: (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid
• InChIKey: UUBHZHZSIKRVIV-KCXSXWJSSA-N
• INCHI: 1S/C20H30O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h8-9,11,13-15H,6-7,10,12H2,1-5H3,(H,21,22)/b14-8+,17-11+,18-13+,19-15+
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/C=C/C(=C/C(=O)O)/C)/C)/C)C
• Alternate CAS: 81485-25-8
• MeSH Entry Terms: (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid;(2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid;3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid;NIK-333;peretinoin
• Molecular Weight: 302.45

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Acyclic diterpenoids
• Alternative Parents: Long-chain fatty acids Methyl-branched fatty acids Unsaturated fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acyclic diterpenoid - Long-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Fatty acyl - Fatty acid - Unsaturated fatty acid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
• External Descriptors: Not available

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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (165.32 mM; Need ultrasonic)
• Sensitivity: light sensitive
• Molecular Weight: 302.500 g/mol
• XLogP3: 6.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 302.225 Da
• Monoisotopic Mass: 302.225 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 496.000
• 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