Acelarin (NUC-1031) - ≥99% , CAS No.840506-29-8

CAS: 840506-29-8 Cat. No.: A414443 Molecular Weight: 580.47

GRADE & PURITY ≥99%

Synonyms

AcelarinNUC1031 | acelarin | (2S)-Benzyl 2-(((((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate | CPF-31 | EX-A4416 | F85498 | SCHEMBL16769342 | Benzyl (2S)-2-((((2R,3R,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Acelarin (NUC-1031) Acelarin (NUC-1031, Fosgemcitabine palabenamide, CPF-31, MTL-007, GTPL7389), a prodrug based on an aryloxy phosphoramidate derivative of gemcitabine, is a DNA synthesis inhibitor with EC50 of 0.2 nM.

Targets

DNA synthesis (Cell-free assay) 0.2 nM(EC50)

In vitro

NUC-1031 is a gemcitabine phosphoramidate prodrug with potent cytostatic activity in a range of different tumor cell lines. Importantly, compared with gemcitabine, NUC-1031 activation is significantly less dependent on deoxycytidine kinase and on nucleoside transporters, and it is resistant to cytidine deaminase-mediated degradation.

In vivo

NUC-1031 shows a significant reduction in tumor volumes in vivo in pancreatic cancer xenografts.

Cell Research(from reference)

Cell lines：Murine leukemia L1210, human lymphocyte CEM 

Concentrations：1 μM 

Incubation Time：1 h 

Specifications

Synonyms

AcelarinNUC1031 | acelarin | (2S)-Benzyl 2-(((((2R, 3R, 5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4, 4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate | CPF-31 | EX-A4416 | F85498 | SCHEMBL16769342 | Benzyl (2S)-2-((((2R, 3R,

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Acelarin (NUC-1031, Fosgemcitabine palabenamide, CPF-31, MTL-007, GTPL7389), a prodrug based on an aryloxy phosphoramidate derivative of gemcitabine, is a DNA synthesis inhibitor with EC50 of 0.2 nM.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Purity

≥99%

Product Properties

• ALogP: 1.69
• hba_count: 7
• HBD Count: 3
• Rotatable Bond: 12

Names and Identifiers

• Pubchem Sid: 504766107
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766107
• Canonical Smiles: CC(C(=O)OCC1=CC=CC=C1)NP(=O)(OCC2C(C(C(O2)N3C=CC(=NC3=O)N)(F)F)O)OC4=CC=CC=C4
• IUPAC Name: benzyl (2S)-2-[[[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
• InChIKey: NHTKGYOMICWFQZ-KKQYNPQSSA-N
• INCHI: 1S/C25H27F2N4O8P/c1-16(22(33)36-14-17-8-4-2-5-9-17)30-40(35,39-18-10-6-3-7-11-18)37-15-19-21(32)25(26,27)23(38-19)31-13-12-20(28)29-24(31)34/h2-13,16,19,21,23,32H,14-15H2,1H3,(H,30,35)(H2,28,29,34)/t16-,19+,21+,23+,40?/m0/s1
• Isomeric SMILES: C[C@@H](C(=O)OCC1=CC=CC=C1)NP(=O)(OC[C@@H]2[C@H](C([C@@H](O2)N3C=CC(=NC3=O)N)(F)F)O)OC4=CC=CC=C4
• Molecular Weight: 580.47
• Reaxy-Rn: 41450278
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=41450278&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: Alpha amino acid esters Alanine and derivatives Benzyloxycarbonyls Phosphoric diester monoamides Phenoxy compounds Pyrimidones Aminopyrimidines and derivatives Hydropyrimidines Organic phosphoramides Imidolactams Oxolanes Heteroaromatic compounds Fluorohydrins Carboxylic acid esters Secondary alcohols Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organofluorides Hydrocarbon derivatives Alkyl fluorides Carbonyl compounds Primary amines Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Alpha-amino acid ester - Alanine or derivatives - Alpha-amino acid or derivatives - Benzyloxycarbonyl - Phenoxy compound - Phosphoric diester monoamide - Aminopyrimidine - Pyrimidone - Monocyclic benzene moiety - Hydropyrimidine - Imidolactam - Organic phosphoric acid amide - Organic phosphoric acid derivative - Benzenoid - Phosphoric acid ester - Pyrimidine - Heteroaromatic compound - Oxolane - Halohydrin - Amino acid or derivatives - Fluorohydrin - Carboxylic acid ester - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Oxacycle - Alcohol - Organohalogen compound - Organofluoride - Organonitrogen compound - Carbonyl group - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Amine - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Alkyl fluoride - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• 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(Human)

Homo sapiens (32628 Activities)

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BXPC-3 (2997 Activities)

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CCRF-CEM (65223 Activities)

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HT-29 (80576 Activities)

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Huh-7 (12904 Activities)

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MIA PaCa-2 (5949 Activities)

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HEL (6614 Activities)

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LNCaP (8286 Activities)

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MV4-11 (7307 Activities)

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CWR22R (2180 Activities)

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JeKo-1 (376 Activities)

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KG-1a (249 Activities)

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MM1.S (1111 Activities)

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Associated Targets(non-human)

Cda Cytidine deaminase (37 Activities)

Discover Target: Cda

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Human alphaherpesvirus 3 (4092 Activities)

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Mus musculus (284745 Activities)

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L1210 (27553 Activities)

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Vero (26788 Activities)

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Serum (58 Activities)

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Liver microsome (341 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 100 mg/mL (172.27 mM); Ethanol: 20 mg/mL (34.45 mM); Water: Insoluble
• DMSO(mg / mL) Max Solubility: 100
• DMSO(mM) Max Solubility: 172.274191603356
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 580.500 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 580.153 Da
• Monoisotopic Mass: 580.153 Da
• Topological Polar Surface Area: 162.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 1020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1