Hastatoside - 10mM in DMSO , CAS No.50816-24-5

CAS: 50816-24-5 Cat. No.: H424371 Molecular Weight: 404.37

GRADE & PURITY 10mM in DMSO

Synonyms

methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate | Hastatoside | 1alpha-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7aalpha-hexahydro-4aalpha

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Product Describtion:

Hastatoside is an iridoid glycoside that is isolated from Verbena officinalis and has a role in promoting sleep.

Specifications

Synonyms

methyl (1S, 4aR, 7S, 7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1, 6, 7, 7a-tetrahydrocyclopenta[c]pyran-4-carboxylate | Hastatoside | 1alpha-(beta-D-Glucopyranosyloxy)-1, 4a, 5, 6, 7, 7aalpha-hexahydro-4aalpha

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CC1CC(=O)C2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
• IUPAC Name: methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChIKey: PRZVXHGUJJPSME-CZMSZWGTSA-N
• INCHI: 1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1
• Isomeric SMILES: C[C@H]1CC(=O)[C@]2([C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• Molecular Weight: 404.37
• Reaxy-Rn: 38523540
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38523540&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 Tertiary alcohols Enoate esters Vinylogous esters Ketones Secondary alcohols Cyclic alcohols and derivatives Acetals Oxacyclic compounds Monocarboxylic acids and derivatives Polyols Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Monosaccharide - Oxane - Cyclic alcohol - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tertiary alcohol - Methyl ester - Secondary alcohol - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Polyol - Acetal - Oxacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Alcohol - Carbonyl group - 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: 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

Chemical and Physical Properties

• Molecular Weight: 404.400 g/mol
• XLogP3: -1.700
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 404.132 Da
• Monoisotopic Mass: 404.132 Da
• Topological Polar Surface Area: 172.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 663.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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

References

1. Qiaoyu He, Yumeng Shi, Hong Xing, Qian Tang, Jing Liu, Chunxia Li, Han Zhang, Boli Zhang, Junhua Zhang, Xiaopeng Chen.  (2022)  Modulating effect of Xuanfei Baidu granule on host metabolism and gut microbiome in rats..  Frontiers in Pharmacology,      [PMID:36147334] [10.3389/fphar.2022.922642]