Gastrodin - Moligand™, ≥98% , CAS No.62499-27-8

CAS: 62499-27-8 Cat. No.: G299059 Formula: C₁₃H₁₈O₇ Molecular Weight: 286.28 EC Number: 683-202-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

(-)-GASTRODIN | 4-(Hydroxymethyl)phenyl beta-D-Glucopyranoside | beta-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL- | Gastrodine | 5YS9U2W3RQ | Gastrodin | UNII-5YS9U2W3RQ | Gastrodin Hemihydrate

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

(-)-GASTRODIN | 4-(Hydroxymethyl)phenyl beta-D-Glucopyranoside | beta-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL- | Gastrodine | 5YS9U2W3RQ | Gastrodin | UNII-5YS9U2W3RQ | Gastrodin Hemihydrate

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Neuroprotective and anticonvulsant agent. Attenuates glutamate accumulation during cerebral ischemia. Regulates Na + and K + currents in small DRG neurons. Shows antidepressant, analgesic and sedative effects in vivo. Blood-brain barrier permeable.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

504756736

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504756736

Canonical Smiles

C1=CC(=CC=C1CO)OC2C(C(C(C(O2)CO)O)O)O

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

InChIKey

PUQSUZTXKPLAPR-UJPOAAIJSA-N

INCHI

1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1

Isomeric SMILES

C1=CC(=CC=C1CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Molecular Weight

286.28

Reaxy-Rn

25441801

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25441801&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glycosyl compounds Phenoxy compounds Phenol ethers Benzyl alcohols Oxanes Monosaccharides Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - O-glycosyl compound - Phenoxy compound - Benzyl alcohol - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - Secondary alcohol - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Alcohol - Hydrocarbon derivative - Primary alcohol - Aromatic alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: glycoside

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)

ABAT Tclin Gamma-amino-N-butyrate transaminase (140 Activities)

Discover Target: ABAT

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

ALDH5A1 Tclin Succinate semialdehyde dehydrogenase (19 Activities)

Discover Target: ALDH5A1

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: ≥12.9 mg/mL in DMSO; ≥18.5 mg/mL in H2O; ≥18.67 mg/mL in EtOH with ultrasonic
• Sensitivity: heat sensitive
• Specific Rotation[α]: -66.0 to -70.0 deg(C=1,H2O)
• Melt Point(°C): 154-155°C
• Molecular Weight: 286.280 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.105 Da
• Monoisotopic Mass: 286.105 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 292.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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