Arteannuin B - ≥99% , CAS No.50906-56-4

CAS: 50906-56-4 Cat. No.: A646382 Molecular Weight: 248.32 EC Number: 683-223-1 PubChem CID: 6543478

GRADE & PURITY ≥99%

Synonyms

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0?,?.0??,??]tetradecan-3-one | 3H-Oxireno(7,8)naphtho(8a,1-b)furan-3-one, decahydro-7,9a-dimethyl-4-methylene-, (1aR-(1aalpha,1bR*,4abeta,7beta,7abeta,9aalpha))- | HY-N2016 | HMS

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Arteannuin B co-occurs with artemisinin, which is the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae). Arteannuin B shows anti-SARS-CoV-2 potential with an EC 50 of 10.28 μM .

Form:Solid

Specifications

Synonyms

(1R, 5S, 8R, 9S, 12R, 14R)-8, 12-dimethyl-4-methylidene-2, 13-dioxatetracyclo[7.5.0.0?, ?.0??, ??]tetradecan-3-one | 3H-Oxireno(7, 8)naphtho(8a, 1-b)furan-3-one, decahydro-7, 9a-dimethyl-4-methylene-, (1aR-(1aalpha, 1bR*, 4abeta, 7beta, 7abeta, 9aalpha))- | HY-N2016 | HMS

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Arteannuin B co-occurs with artemisinin, which is the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae). Arteannuin B shows anti-SARS-CoV-2 potential with an EC 50 of 10.28 μM.

Storage

Protected from light, 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.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1CCC2C(=C)C(=O)OC23C1CCC4(C3O4)C
• IUPAC Name: (1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one
• InChIKey: QWQSMEDUZQDVLA-KPHNHPKPSA-N
• INCHI: 1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1
• Isomeric SMILES: C[C@@H]1CC[C@H]2C(=C)C(=O)O[C@]23[C@H]1CC[C@@]4([C@H]3O4)C
• Alternate CAS: 50906-56-4
• PubChem CID: 6543478
• MeSH Entry Terms: arteannuin B
• Molecular Weight: 248.32

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones
        • Level5 Sesquiterpene lactones
          • Level6 Cadinanolides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Sesquiterpene lactones
• Direct Parent: Cadinanolides
• Alternative Parents: Sesquiterpenoids Oxepanes Gamma butyrolactones Oxolanes Enoate esters Oxacyclic compounds Monocarboxylic acids and derivatives Epoxides Dialkyl ethers Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cadinanolide skeleton - Sesquiterpenoid - Oxepane - Gamma butyrolactone - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Oxolane - Carboxylic acid ester - Lactone - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Oxacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan.
• 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

Associated Targets(Human)

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

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

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

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

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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

ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

Discover Target: ATAD5

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

ATXN2 Tbio Ataxin-2 (54410 Activities)

Discover Target: ATXN2

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

Associated Targets(non-human)

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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

Mitf Microphthalmia-associated transcription factor (11 Activities)

Discover Target: Mitf

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 25 mg/mL (100.68 mM; Need ultrasonic)
• Molecular Weight: 248.320 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.141 Da
• Monoisotopic Mass: 248.141 Da
• Topological Polar Surface Area: 38.800 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 457.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• 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. Yuting Li, Luhan Wang, Minhua Qian, Shengda Qi, Lei Zhou, Qiaosheng Pu.  (2022)  Concise analysis of γ-hydroxybutyric acid in beverages and urine by capillary electrophoresis with capacitively coupled contactless conductivity detection using 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid as background electrolyte.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:35675730] [10.1016/j.chroma.2022.463191]

2. Xiao-Chong Tang, Yi Xiao, Ping Li, Lian-Wen Qi.  (2018)  Simple, Fast, and Sensitive detection of artemisinin in human serum and Artemisia annua using microsensor array coupled with electrochemiluminescent imaging technique.  TALANTA,      [PMID:30683341] [10.1016/j.talanta.2018.12.016]