Geniposide - analytical standard, Moligand™, ≥98% , CAS No.24512-63-8

CAS: 24512-63-8 Cat. No.: G101668 Formula: C₁₇H₂₄O₁₀ Molecular Weight: 388.37 EC Number: 683-175-1

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

DTXSID101318419 | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)- | (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

DTXSID101318419 | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)- | (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c

Specifications & Purity

analytical standard, Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. Geniposide has been shown to regulate Nrf2 translocation and upregulate downstream antioxid

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard, Moligand™

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

528769867

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528769867

Canonical Smiles

COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O

IUPAC Name

methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

InChIKey

IBFYXTRXDNAPMM-BVTMAQQCSA-N

INCHI

1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1

Isomeric SMILES

COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

WGK Germany

3

Molecular Weight

388.37

Reaxy-Rn

33425786

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33425786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Iridoid O-glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Bicyclic monoterpenoids Iridoids and derivatives Oxanes Methyl esters Enoate esters Vinylogous esters Secondary alcohols Oxacyclic compounds Polyols Monocarboxylic acids and derivatives Acetals Organic oxides Primary alcohols Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Monosaccharide - Oxane - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Secondary alcohol - Acetal - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Carboxylic acid derivative - Polyol - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Primary alcohol - Organic oxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
• External Descriptors: Iridoids

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)

XDH Tclin Xanthine dehydrogenase (1038 Activities)

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PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)

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PTPN11 Tchem Protein-tyrosine phosphatase 2C (2297 Activities)

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Raji (5516 Activities)

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dsDNA (365 Activities)

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quadruplex DNA (2700 Activities)

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HK-2 (249 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Mus musculus (284745 Activities)

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Hepatitis C virus (23859 Activities)

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Enterovirus A71 (1246 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Drosophila (190 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Specific Rotation[α]: 15° (C=1,EtOH)
• Melt Point(°C): 162°C
• Molecular Weight: 388.400 g/mol
• XLogP3: -2.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 388.137 Da
• Monoisotopic Mass: 388.137 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 617.000
• 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