Paraherquamide A - Moligand™, ≥95% , CAS No.77392-58-6

CAS: 77392-58-6 Cat. No.: P329400 Formula: C₂₈H₃₅N₃O₅ Molecular Weight: 493.6 Beilstein Registry Number: 3599562 PubChem CID: 156934

GRADE & PURITY Moligand™, ≥95%

Synonyms

(-)-Paraherquamide A | (1'S,6'R,7'R,8R,9'S)-6'-hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione | Q27287870 | NSC784317 | NSC-784317 | Paraherquamide | R72VB4E4K

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Paraherquamide A is a mycotoxin anthelmintic originally isolated from P. paraherquei. It binds to acetylcholine receptors (IC50 = 0.5 nM for head homogenates of M. domestica) and acts as an antagonist. Paraherquamide A is toxic to C. elegans (LD50 = 2.5 µg/ml) and effective against T. colubriformis infection in gerbils when used at doses ranging from 0.39 to 200 mg/kg. It is toxic to mice (LD50 = 14.9 mg/kg).

Specifications

Synonyms

(-)-Paraherquamide A | (1'S,6'R,7'R,8R,9'S)-6'-hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione | Q27287870 | NSC784317 | NSC-784317 | Paraherquamide | R72VB4E4K

Specifications & Purity

Moligand™, ≥95%

Storage

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

Moligand™

Purity

≥95%

Names and Identifiers

Canonical Smiles

CC1(C=COC2=C(O1)C=CC3=C2NC(=O)C34CC56CN7CCC(C7(CC5C4(C)C)C(=O)N6C)(C)O)C

IUPAC Name

(1'S,6'R,7'R,8R,9'S)-6'-hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione

InChIKey

UVZZDDLIOJPDKX-ITKQZBBDSA-N

INCHI

1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1

Isomeric SMILES

C[C@]1(CCN2[C@]13C[C@@H]4[C@](C2)(C[C@@]5(C4(C)C)C6=C(C7=C(C=C6)OC(C=CO7)(C)C)NC5=O)N(C3=O)C)O

RTECS

RV0545000

PubChem CID

156934

Molecular Weight

493.6

Beilstein

3599562

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azaspirodecane derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azaspirodecane derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Azaspirodecane derivatives
• Alternative Parents: Alpha amino acids and derivatives Indolines Indolizidines 1,4-dioxepines Alkyl aryl ethers Aralkylamines Piperidinones Delta lactams N-methylpiperazines Benzenoids N-alkylpyrrolidines Tertiary alcohols Tertiary carboxylic acid amides Trialkylamines Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - Azaspirodecane - Indole or derivatives - Dihydroindole - Indolizidine - 1,4-dioxepine - Alkyl aryl ether - Delta-lactam - Dioxepine - Aralkylamine - N-alkylpiperazine - N-methylpiperazine - Piperidinone - 1,4-diazinane - Benzenoid - N-alkylpyrrolidine - Piperazine - Piperidine - Tertiary carboxylic acid amide - Tertiary alcohol - Pyrrolidine - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Lactam - Amino acid or derivatives - Carboxamide group - Azacycle - Ether - Oxacycle - Carboxylic acid derivative - Amine - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxide - Alcohol - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.
• 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

• Solubility: Soluble in ethanol, methanol, DMF, DMSO, and water (poorly).
• Refractive Index: n20D1.67 (Predicted)
• Boil Point(°C): 682.78° C at 760 mmHg (Predicted)
• Melt Point(°C): 290.08° C (Predicted)
• Molecular Weight: 493.600 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 493.258 Da
• Monoisotopic Mass: 493.258 Da
• Topological Polar Surface Area: 91.300 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 1090.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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