Polyoxin D, Streptomyces cacaoi var. asoensis - ≥95% , CAS No.22976-86-9

CAS: 22976-86-9 Cat. No.: P349861 Molecular Weight: 521.39 PubChem CID: 72476

GRADE & PURITY ≥95%

Synonyms

5-Pyrimidinecarboxylic acid, 1-(5-(2-amino-2-deoxy-L-xylonamido)-5-deoxy-beta-D-allofuranuronosyl)-1,2,3,4-tetrahydro-2,4-dioxo-, monocarbamate (ester) | .beta.-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy

Storage

Room temperature,Desiccated

Shipped In

Normal

Overview

Polyoxin D, Streptomyces cacaoi var. asoensis is a specific inhibitor of fungal chitin synthetase. As a nucleoside-dipeptide antibiotic, Polyoxin D, Streptomyces cacaoi var. asoensis is studied comparatively to nikkomycin Z. Polyoxin D, Streptomyces cacaoi var. asoensis behaves as a potent, competitive inhibitor of enzyme activity. In B. cinerea microsomes, Polyoxin D, Streptomyces cacaoi var. asoensis was able to inhibit chitin synthase with a K|i|value of 6 μM. Polyoxin D, Streptomyces cacaoi var. asoensis also affects germ tubes, altering their morphology and inhibiting spore germination.

Specifications

Synonyms

5-Pyrimidinecarboxylic acid, 1-(5-(2-amino-2-deoxy-L-xylonamido)-5-deoxy-beta-D-allofuranuronosyl)-1, 2, 3, 4-tetrahydro-2, 4-dioxo-, monocarbamate (ester) | .beta.-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy

Specifications & Purity

≥95%

Storage

Room temperature, Desiccated

Shipped In

Normal

Purity

≥95%

Product Properties

• Ki Data: fungal chitin synthetase: Ki= 6 μM

Names and Identifiers

• Canonical Smiles: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)C(C(=O)O)NC(=O)C(C(C(COC(=O)N)O)O)N)O)O)C(=O)O
• IUPAC Name: 1-[(2R,3R,4S,5R)-5-[(S)-[[(2S,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-carboxymethyl]-3,4-dihydroxyoxolan-2-yl]-2,4-dioxopyrimidine-5-carboxylic acid
• InChIKey: JPFWJDMDPLEUBD-ITJAGOAWSA-N
• INCHI: 1S/C17H23N5O14/c18-5(7(24)4(23)2-35-16(19)33)12(28)20-6(15(31)32)10-8(25)9(26)13(36-10)22-1-3(14(29)30)11(27)21-17(22)34/h1,4-10,13,23-26H,2,18H2,(H2,19,33)(H,20,28)(H,29,30)(H,31,32)(H,21,27,34)/t4-,5-,6-,7+,8-,9+,10+,13+/m0/s1
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)[C@@H](C(=O)O)NC(=O)[C@H]([C@@H]([C@H](COC(=O)N)O)O)N)O)O)C(=O)O
• RTECS: UV7717100
• PubChem CID: 72476
• Molecular Weight: 521.39

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: 5'-deoxyribonucleosides N-acyl-alpha amino acids Glycosylamines Pyrimidinecarboxylic acids Hydropyrimidine carboxylic acids and derivatives Pyrimidones Hydroxypyrimidines Dicarboxylic acids and derivatives Vinylogous amides Vinylogous acids Tetrahydrofurans 1,3-aminoalcohols Heteroaromatic compounds Secondary alcohols Amino acids Propargyl-type 1,3-dipolar organic compounds Polyols Oxacyclic compounds Azacyclic compounds Carboximidic acids Carboxylic acids Carbonyl compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Imines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha peptide - 5'-deoxyribonucleoside - N-acyl-alpha amino acid or derivatives - N-acyl-alpha-amino acid - Glycosyl compound - N-glycosyl compound - Alpha-amino acid or derivatives - Pyrimidine-5-carboxylic acid - Pyrimidine-5-carboxylic acid or derivatives - Hydropyrimidine carboxylic acid derivative - Pyrimidone - Hydroxypyrimidine - Dicarboxylic acid or derivatives - Pyrimidine - Hydropyrimidine - Heteroaromatic compound - Tetrahydrofuran - 1,3-aminoalcohol - Vinylogous acid - Vinylogous amide - Secondary alcohol - Amino acid - Amino acid or derivatives - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Oxacycle - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Polyol - Organopnictogen compound - Amine - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Imine - Primary aliphatic amine - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: antibiotic fungicide - polyoxin

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)

Aspergillus flavus (8875 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida (1648 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, and Aqueous Buffers.
• Refractive Index: n20D1.69 (Predicted)
• Molecular Weight: 521.400 g/mol
• XLogP3: -7.500
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 11
• Exact Mass: 521.124 Da
• Monoisotopic Mass: 521.124 Da
• Topological Polar Surface Area: 322.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 971.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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