Mesaconitine - analytical standard, ≥96% , CAS No.2752-64-9

CAS: 2752-64-9 Cat. No.: M115190 Molecular Weight: 631.71 EC Number: 220-397-6

GRADE & PURITY Analytical standard, ≥96%

Synonyms

N-desethyl-N-methylaconitine | AKOS025311469 | C08698 | Japaconitine B | Mesaconitine | Q-100349 | Q27107326 | XUHJBXVYNBQQBD-TUWOXVOMSA-N | Japaconitine A | s3236 | CHEBI:6773

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

N-desethyl-N-methylaconitine | AKOS025311469 | C08698 | Japaconitine B | Mesaconitine | Q-100349 | Q27107326 | XUHJBXVYNBQQBD-TUWOXVOMSA-N | Japaconitine A | s3236 | CHEBI:6773

Specifications & Purity

analytical standard, ≥96%

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Purity

≥96%

Names and Identifiers

• Canonical Smiles: CC(=O)OC12C3C(CC(C3OC(=O)C4=CC=CC=C4)(C(C1O)OC)O)C56C(CC(C7(C5C(C2C6N(C7)C)OC)COC)O)OC
• IUPAC Name: [(1S,2R,3R,4R,5R,6S,7S,8R,9R,13R,14R,16S,17S,18R)-8-acetyloxy-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
• InChIKey: XUHJBXVYNBQQBD-TUWOXVOMSA-N
• INCHI: 1S/C33H45NO11/c1-16(35)45-33-21-18(13-31(39,28(43-6)26(33)37)27(21)44-29(38)17-10-8-7-9-11-17)32-20(41-4)12-19(36)30(15-40-3)14-34(2)25(32)22(33)23(42-5)24(30)32/h7-11,18-28,36-37,39H,12-15H2,1-6H3/t18-,19-,20+,21-,22+,23+,24-,25?,26+,27-,28+,30+,31-,32+,33-/m1/s1
• Isomeric SMILES: CC(=O)O[C@@]12[C@@H]3[C@@H](C[C@@]([C@@H]3OC(=O)C4=CC=CC=C4)([C@H]([C@@H]1O)OC)O)[C@]56[C@H](C[C@H]([C@@]7([C@H]5[C@H]([C@H]2C6N(C7)C)OC)COC)O)OC
• Molecular Weight: 631.71
• Reaxy-Rn: 1560036
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1560036&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Aconitane-type diterpenoid alkaloids
• Alternative Parents: Benzoic acid esters Quinolidines Alkaloids and derivatives Benzoyl derivatives Azepanes Dicarboxylic acids and derivatives Piperidines Tertiary alcohols Trialkylamines Cyclic alcohols and derivatives Carboxylic acid esters Secondary alcohols Amino acids and derivatives Dialkyl ethers Polyols Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aconitane-type diterpenoid alkaloid - Benzoate ester - Quinolidine - Benzoic acid or derivatives - Alkaloid or derivatives - Benzoyl - Azepane - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Piperidine - Benzenoid - Cyclic alcohol - Tertiary alcohol - Tertiary aliphatic amine - Secondary alcohol - Tertiary amine - Amino acid or derivatives - Carboxylic acid ester - Polyol - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Dialkyl ether - Ether - Organopnictogen compound - Carbonyl group - Alcohol - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Amine - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.
• External Descriptors: diterpenoid

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)

DU-145 (51482 Activities)

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

A549 (127892 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 631.700 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 631.299 Da
• Monoisotopic Mass: 631.299 Da
• Topological Polar Surface Area: 153.000 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 1200.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 1
• 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. Long Zhang, Ping Hang, Xi-Yi Zhou, Wen-Jing Qiao, Jian-Dong Jiang.  (2020)  Enantioselective Catabolism of the Two Enantiomers of the Phenoxyalkanoic Acid Herbicide Dichlorprop by Sphingopyxis sp. DBS4.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:32530641] [10.1021/acs.jafc.0c01066]