(5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine

Basic Information

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CAS Number

58944-73-3

Molecular Formula

C15H23N7O5

Molecular Weight

381.39 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Solubility

H2O: soluble

Specific Rotation

D25 -2.61° (c = 5 in water); D23 +12 ±2° (c = 0.227 in water)

SMILES

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C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CC(CCC(C(=O)O)N)N)O)O)N

InChI

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

InChIKey

LMXOHSDXUQEUSF-YECHIGJVSA-N

LogP

-2.0627999999999966

pKa

pKa (66% DMF): 2.9, 3.9, 8.9, 10.2(at 25℃)

Topological Polar Surface Area

208.65 Å²

Hydrogen Bond Donor/Acceptor

9 / 12

Complexity

529

Safety Information

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Toxicity

LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)

Synonyms & References

English

6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid
UNII-W2U467CIIL
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid
SINEFUNGIN [INN]
(2S,5S)-2,5-Diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-2-tetrahydrofuryl]hexanoic Acid
LMXOHSDXUQEUSF-YECHIGJVSA-N
Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-, (beta-D-ribo)-
Antibiotic 32232 RP
A-9145
BCP28648
ADENOSYL-ORNITHINE
BS162746
sinefungin
LILLY 57926
D05846
Sinefungina [INN-Spanish]
Sinefungine
BRN 3574678
Sinefungin [USAN:INN]
CHEMBL1214186
RP 32232
D-glycero-alpha-L-talo-Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
(2S,5S)-2,5-diamino-6-((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)hexanoic acid
(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid (non-preferred name)
Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
LY-57926
(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid
Compound 57926
SINEFUNGIN [MI]
SINEFUNGIN [USAN]

MDL Number

MFCD00057013

FAQ

What regulatory guidelines apply to (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3)?

Regulatory guidelines for (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) include classification under the Globally Harmonized System of Classification and Labeling of Chemicals (GHS), which covers health, environmental, and physical hazards. Additionally, it is subject to the European Union’s REACH regulations for chemical safety assessment and management. In the U.S., it falls under the jurisdiction of the FDA for drug-related applications and the EPA for environmental regulation.

Are there alternatives to (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) in synthesis?

In synthesis, (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) can be synthesized using analogs such as (5S)-5-amino-6-[(2R,3S,4R,5R)-5-(6-bromo-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine or other isomers. Common alternatives include 6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-5-amino-L-norleucine, which can be used as a starting material in place of the target compound, depending on the specific application.

What is the market or research trend for (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3)?

The market and research trend for (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) is focused on its potential in pharmaceuticals, particularly in the development of nucleoside analogs for antiviral and anticancer treatments. Recent research highlights its role in drug discovery and development, with increasing interest in its biological activities and therapeutic potential.

How should waste containing (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) be handled?

Waste containing (5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine (CAS: 58944-73-3) should be handled according to proper waste management protocols. It should be collected in appropriate containers and disposed of through incineration or professional waste disposal services. Environmental protection precautions include ensuring that waste does not contaminate soil or water sources, and that all handling and disposal procedures comply with local, state, and federal regulations.