Sinefungin(A-9145) - Moligand™, ≥95% , CAS No.58944-73-3

CAS: 58944-73-3 Cat. No.: S275398 Molecular Weight: 381.39 EC Number: 637-385-5 PubChem CID: 65482

GRADE & PURITY Moligand™, ≥95%

Synonyms

BRN 3574678 | Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-, (beta-D-ribo)- | LILLY 57926 | Sinefungine | TCA-O-PCP?Trichloroacetic acid pentachlorophenyl ester | LY-57926 | DB01910 | Q27093021 | 6,9-Diamino-1-(6-amino

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Sinefungin is a natural nucleoside analog of S-adenosylmethionine and inhibits Streptococcus pneumoniae biofilm growth. Its derivatives can be used as inhibitors and structure probes for human protein lysine methyltransferase SETD2.

Specifications

Synonyms

BRN 3574678 | Decofuranuronic acid, 6, 9-diamino-1-(6-amino-9H-purin-9-yl)-1, 5, 6, 7, 8, 9-hexadeoxy-, (beta-D-ribo)- | LILLY 57926 | Sinefungine | TCA-O-PCP?Trichloroacetic acid pentachlorophenyl ester | LY-57926 | DB01910 | Q27093021 | 6, 9-Diamino-1-(6-amino

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Potent, competitive methyltransferase inhibitor (IC 50 values are < 1 and 2.5 μM for PRMT1 abd SET7/9 respectively). Nucleoside S-adenosylmethionine analog. Inhibits RNA synthesis. Shows antibacterial effects.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

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

≥95%

Names and Identifiers

• Pubchem Sid: 488183684
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183684
• Canonical Smiles: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CC(CCC(C(=O)O)N)N)O)O)N
• IUPAC Name: (2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
• InChIKey: LMXOHSDXUQEUSF-YECHIGJVSA-N
• INCHI: 1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)C[C@H](CC[C@@H](C(=O)O)N)N)O)O)N
• WGK Germany: 3
• RTECS: HE3140000
• PubChem CID: 65482
• Molecular Weight: 381.39

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class 5'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: 5'-deoxyribonucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: 5'-deoxyribonucleosides
• Alternative Parents: Glycosylamines 6-aminopurines Pentoses L-alpha-amino acids Medium-chain fatty acids Amino fatty acids Aminopyrimidines and derivatives Heterocyclic fatty acids Hydroxy fatty acids N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds 1,2-diols Secondary alcohols Amino acids Carboxylic acids Azacyclic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organopnictogen compounds Carbonyl compounds Monoalkylamines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5'-deoxyribonucleoside - N-glycosyl compound - Glycosyl compound - Pentose monosaccharide - 6-aminopurine - L-alpha-amino acid - Alpha-amino acid or derivatives - Alpha-amino acid - Imidazopyrimidine - Purine - Medium-chain fatty acid - Hydroxy fatty acid - Amino fatty acid - Aminopyrimidine - Heterocyclic fatty acid - N-substituted imidazole - Monosaccharide - Fatty acyl - Fatty acid - Pyrimidine - Imidolactam - Imidazole - Azole - Heteroaromatic compound - Tetrahydrofuran - Amino acid or derivatives - 1,2-diol - Secondary alcohol - Amino acid - Oxacycle - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organopnictogen compound - Carbonyl group - Alcohol - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
• External Descriptors: adenosines - non-proteinogenic alpha-amino acid

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)

EHMT2 Tchem Histone-lysine N-methyltransferase EHMT2 (1 Activities)

Discover Target: EHMT2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EHMT1 Tchem Histone-lysine N-methyltransferase EHMT1 (1 Activities)

Discover Target: EHMT1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RNMT Tchem mRNA cap guanine-N7 methyltransferase (1 Activities)

Discover Target: RNMT

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DNMT3A Tclin DNA (cytosine-5)-methyltransferase 3A (310 Activities)

Discover Target: DNMT3A

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

INMT Tchem Indolethylamine N-methyltransferase (111 Activities)

Discover Target: INMT

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

PCMT1 Tbio Protein-beta-aspartate methyltransferase (8 Activities)

Discover Target: PCMT1

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

TPMT Tchem Thiopurine S-methyltransferase (45 Activities)

Discover Target: TPMT

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

HL-60 (67320 Activities)

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

A549 (127892 Activities)

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

HEK293 (82097 Activities)

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

HepG2 (196354 Activities)

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

MDA-MB-231 (73002 Activities)

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

SETD7 Tchem Histone-lysine N-methyltransferase SETD7 (390 Activities)

Discover Target: SETD7

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

PRMT1 Tchem Protein-arginine N-methyltransferase 1 (867 Activities)

Discover Target: PRMT1

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

EHMT1 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 5 (407 Activities)

Discover Target: EHMT1

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

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

PRMT5 Tchem Protein arginine N-methyltransferase 5 (1273 Activities)

Discover Target: PRMT5

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

DOT1L Tchem Histone-lysine N-methyltransferase, H3 lysine-79 specific (648 Activities)

Discover Target: DOT1L

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

NNMT Tchem Nicotinamide N-methyltransferase (469 Activities)

Discover Target: NNMT

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

RNMT Tchem mRNA cap guanine-N7 methyltransferase (30 Activities)

Discover Target: RNMT

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

TRDMT1 Tbio tRNA (cytosine(38)-C(5))-methyltransferase (277 Activities)

Discover Target: TRDMT1

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

GNMT Tchem Glycine N-methyltransferase (70 Activities)

Discover Target: GNMT

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

NSUN2 Tbio RNA cytosine C(5)-methyltransferase NSUN2 (11 Activities)

Discover Target: NSUN2

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

Associated Targets(non-human)

Leishmania donovani (89745 Activities)

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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

Nonstructural protein 5 (92 Activities)

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

Zika virus (1028 Activities)

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

SARS-CoV-2 (38078 Activities)

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

NS5 (58 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water
• Molecular Weight: 381.390 g/mol
• XLogP3: -4.300
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 381.176 Da
• Monoisotopic Mass: 381.176 Da
• Topological Polar Surface Area: 209.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 529.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Rui-Li Zhu, Ying-Kun Zhi, Lang Yi, Jin-Fang Luo, Jing Li, Sha-Sha Bai, Liang Liu, Pei-Xun Wang, Hua Zhou, Yan Dong.  (2019)  Sinomenine regulates CD14/TLR4, JAK2/STAT3 pathway and calcium signal via α7nAChR to inhibit inflammation in LPS-stimulated macrophages.  IMMUNOPHARMACOLOGY AND IMMUNOTOXICOLOGY,      [PMID:30896303] [10.1080/08923973.2019.1568451]

2. Lang Yi, Yan-jun Lyn, Chong Peng, Rui-li Zhu, Sha-sha Bai, Liang Liu, Pei-xun Wang, Hua Zhou, Yan Dong.  (2018)  Sinomenine inhibits fibroblast-like synoviocyte proliferation by regulating α7nAChR expression via ERK/Egr-1 pathway.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:29367088] [10.1016/j.intimp.2018.01.015]

3. Biao Zhou, Xiaolong Lu, Zhi Tang, Dan Liu, Youliang Zhou, Peng Zeng, Hui Xiong.  (2017)  Influence of sinomenine upon mesenchymal stem cells in osteoclastogenesis.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:28437887] [10.1016/j.biopha.2017.03.084]