Fosifloxuridine nafalbenamide , CAS No.1332837-31-6

CAS: 1332837-31-6 Cat. No.: F646347 Molecular Weight: 613.53 PubChem CID: 53373585

Synonyms

N-(2'-Deoxy-5-fluoro-P-1-naphthalenyl-5'-uridylyl)-L-alanine phenylmethyl ester | 1332837-31-6 | NUC-3373 | CPF-373 | FOSIFLOXURIDINE NAFALBENAMIDE [INN] | benzyl (2S)-2-[[[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-napht

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Fosifloxuridine nafalbenamide (NUC-3373), a pyrimidine nucleotide analogue, is a Thymidylate synthase inhibitor. Fosifloxuridine nafalbenamide has anticancer activity. Fosifloxuridine nafalbenamide has the potential to evoke a host immune response and enhance immunoresearch.

In Vitro

Fosifloxuridine nafalbenamide induces the release of damage-associated molecular patterns (DAMPs), with increased expression of calreticulin (CRT) at the cell surface and concomitant loss of nuclear nuclear high mobility group box protein 1 (HMGB1). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Fosifloxuridine nafalbenamide exhibits anti-cancer activity in HT-29 nude mouse xenograft models. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

N-(2'-Deoxy-5-fluoro-P-1-naphthalenyl-5'-uridylyl)-L-alanine phenylmethyl ester | 1332837-31-6 | NUC-3373 | CPF-373 | FOSIFLOXURIDINE NAFALBENAMIDE [INN] | benzyl (2S)-2-[[[(2R, 3S, 5R)-5-(5-fluoro-2, 4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-napht

Biochemical and Physiological Mechanisms

Fosifloxuridine nafalbenamide (NUC-3373), a pyrimidine nucleotide analogue, is a Thymidylate synthase inhibitor. Fosifloxuridine nafalbenamide has anticancer activity. Fosifloxuridine nafalbenamide has the potential to evoke a host immune response and enh

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

Names and Identifiers

• Canonical Smiles: CC(C(=O)OCC1=CC=CC=C1)NP(=O)(OCC2C(CC(O2)N3C=C(C(=O)NC3=O)F)O)OC4=CC=CC5=CC=CC=C54
• IUPAC Name: benzyl (2S)-2-[[[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate
• InChIKey: BIOWRMNRHMERIO-ZVAHOJSLSA-N
• INCHI: 1S/C29H29FN3O9P/c1-18(28(36)39-16-19-8-3-2-4-9-19)32-43(38,42-24-13-7-11-20-10-5-6-12-21(20)24)40-17-25-23(34)14-26(41-25)33-15-22(30)27(35)31-29(33)37/h2-13,15,18,23,25-26,34H,14,16-17H2,1H3,(H,32,38)(H,31,35,37)/t18-,23-,25+,26+,43?/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=C(C(=O)NC3=O)F)O)OC4=CC=CC5=CC=CC=C54
• Alternate CAS: 1332837-31-6
• PubChem CID: 53373585
• MeSH Entry Terms: NUC-3073
• Molecular Weight: 613.53

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 Naphthalenes Benzyloxycarbonyls Phosphoric diester monoamides Halopyrimidines Pyrimidones Hydropyrimidines Organic phosphoramides Aryl fluorides Vinylogous amides Heteroaromatic compounds Oxolanes Secondary alcohols Ureas Carboxylic acid esters Lactams Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Carbonyl compounds Organofluorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Alpha-amino acid ester - Alanine or derivatives - Alpha-amino acid or derivatives - Naphthalene - Benzyloxycarbonyl - Phosphoric diester monoamide - Pyrimidone - Halopyrimidine - Organic phosphoric acid derivative - Phosphoric acid ester - Aryl fluoride - Organic phosphoric acid amide - Monocyclic benzene moiety - Benzenoid - Hydropyrimidine - Aryl halide - Pyrimidine - Oxolane - Heteroaromatic compound - Vinylogous amide - Carboxylic acid ester - Urea - Lactam - Secondary alcohol - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Oxacycle - Organic oxygen compound - Organic nitrogen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organooxygen compound - Organofluoride - Organonitrogen compound - Aromatic heteropolycyclic 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)

CCRF-CEM (65223 Activities)

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HT-29 (80576 Activities)

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HCT-116 (91556 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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SW-620 (52400 Activities)

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Associated Targets(non-human)

L1210 (27553 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (162.99 mM; Need ultrasonic)
• Molecular Weight: 613.500 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 613.163 Da
• Monoisotopic Mass: 613.163 Da
• Topological Polar Surface Area: 153.000 Ų
• Heavy Atom Count: 43
• Formal Charge: 0
• Complexity: 1100.000
• 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