Verbenalin - ≥98%(HPLC) , CAS No.548-37-8

CAS: 548-37-8 Cat. No.: C170930 Molecular Weight: 388.37 Beilstein Registry Number: 57895 EC Number: 805-342-1

GRADE & PURITY ≥98%(HPLC)

Synonyms

CCG-268497 | UNII-FZG87K1MQ6 | SMR001397179 | HMS2198M18 | Verbenaloside | 2-chloro-1,3-dinitro-benzene | Verbenalol β-D-glucopyranoside | Verbenalin

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

CCG-268497 | UNII-FZG87K1MQ6 | SMR001397179 | HMS2198M18 | Verbenaloside | 2-chloro-1, 3-dinitro-benzene | Verbenalol β-D-glucopyranoside | Verbenalin

Specifications & Purity

≥98%(HPLC)

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.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504754706
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754706
• Canonical Smiles: [H][C@@]12[C@@H](C)CC(=O)[C@]1([H])C(=CO[C@H]2O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)OC
• IUPAC Name: methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• InChIKey: HLXRWTJXGMHOFN-XJSNKYLASA-N
• INCHI: 1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
• Isomeric SMILES: C[C@H]1CC(=O)[C@H]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
• Molecular Weight: 388.37
• Beilstein: 57895
• Reaxy-Rn: 57895
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=57895&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 Vinylogous esters Enoate esters Methyl esters Secondary alcohols Ketones Acetals Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Primary alcohols
• 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 - Secondary alcohol - Ketone - Carboxylic acid ester - Polyol - Carboxylic acid derivative - Acetal - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Carbonyl group - Organooxygen compound - Primary alcohol - 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: Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids

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)

SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

Discover Target: SMAD3

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

Associated Targets(non-human)

Hepatitis C virus (23859 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light & air sensitive
• Molecular Weight: 388.400 g/mol
• XLogP3: -1.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 388.137 Da
• Monoisotopic Mass: 388.137 Da
• Topological Polar Surface Area: 152.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 619.000
• 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]

2. Qiyue Sun, Ronghua Zhao, Shuran Li, Weiqin Zhou, Jingsheng Zhang, Bo Pang, Shilan Ding, Lei Bao, Zihan Geng, Rui Xie, Dan Xie, Xiaolan Cui, Shanshan Guo, Jing Sun.  (2025)  Verbenalin protects against coronavirus pneumonia by promoting host immune homeostasis. Evidences for its mechanism of action.  PHYTOMEDICINE,      [PMID:40347923] [10.1016/j.phymed.2025.156820]