Shikimic acid - 10mM in DMSO , CAS No.138-59-0

CAS: 138-59-0 Cat. No.: S421460 Fórmula: C₇H₁₀O₅ Peso molecular: 174.15 Beilstein Registry Number: 2210055 Número CE: 205-334-2 PubChem CID: 8742

GRADE & PURITY 10mM in DMSO

Synonyms

shikimic acid|138-59-0|shikimate|L-Shikimic acid|(-)-Shikimic acid|(3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID|(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid|1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-|(3R,4S,

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Visão geral

Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots. It has also been used as a substrate in shikimate kinase assay. Shikimic acid is observed to be carcinogenic in rat models, when administered.It serves as a precursor for the biosynthesis of aromatic amino acids, alkaloids and other aromatic metabolites in microorganisms. Shikimic acid is known to inhibit adenosine diphosphate (ADP) induced platelet aggregation and blood coagulation in rabbits.

Specifications

Sinónimos

shikimic acid | 138-59-0 | shikimate | L-Shikimic acid | (-)-Shikimic acid | (3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID | (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid | 1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- | (3R,4S,

Especificações e pureza

10mM in DMSO

Mecanismos bioquímicos e fisiológicos

Precursor for aromatic amino acid biosynthesis. Promotes increased leaf conductivity, transpiration rate, photosynthetic pigments and growth in plants. Used in the synthesis of many biochemical products.

Condições de armazenamento de armazenamento

Store at -80°C

Enviado em

Dry ice packs + Cold packs

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

Pubchem Sid

528752732

Sorrisos canónicos

C1C(C(C(C=C1C(=O)O)O)O)O

IUPAC Name

(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid

InChIKey

JXOHGGNKMLTUBP-HSUXUTPPSA-N

INCHI

1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

SMILES isoméricas

C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O

WGK Alemanha

3

RTECS

GW4600000

PubChem CID

8742

Peso molecular

174.15

Beilstein

2210055

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Cyclic alcohols and derivatives
          • Level6 Cyclitols and derivatives
            • Level7 Shikimic acids and derivatves

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Cyclic alcohols and derivatives - Cyclitols and derivatives
• Direct Parent: Shikimic acids and derivatves
• Alternative Parents: Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Shikimic acid or derivatives - Secondary alcohol - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.
• External Descriptors: alpha,beta-unsaturated monocarboxylic acid - cyclohexenecarboxylic acid - hydroxy monocarboxylic 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

Alvos associados (humanos)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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SELL Tchem Leukocyte adhesion molecule-1 (145 Activities)

Discover Target: SELL

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HL-60 (67320 Activities)

Explore this target

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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UGT1A6 Tbio UDP-glucuronosyltransferase 1-6 (221 Activities)

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UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)

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Alvos associados (não humanos)

Sele Selectin E (1 Activities)

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Selp P-selectin (7 Activities)

Discover Target: Selp

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aroA 5-enolpyruvylshikimate-3-phosphate synthase (102 Activities)

Discover Target: aroA

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Mecanismos de ação

Propriedades químicas e físicas

• Sensibilidade: Hygroscopic.
• Rotação específica [α]: -180 ° (C=1, H2O)
• Ponto de fusão (°C): 185-187°C
• Peso molecular: 174.150 g/mol
• XLogP3: -1.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 174.053 Da
• Monoisotopic Mass: 174.053 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 222.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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