Ammothamnine - ≥98%(HPLC) , CAS No.16837-52-8

CAS: 16837-52-8 Cat. No.: A111286 Molecular Weight: 264.36 EC Number: 605-514-4

GRADE & PURITY ≥98%(HPLC)

Synonyms

Pachycarpidine | BDBM50597716 | Oxymatrine | BBL030371 | MLS001215101 | rel-(41S,7aS,13aR,13bR)-10-Oxohexadecahydrodipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine 4-oxide | Matrine 1beta-oxide | Ammothamnine | SCHEMBL13394285 | Oxysophoridine | DTXSID409374

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Alkaloid isolated from Sophora flavescens. Antifribotic.

Specifications

Synonyms

Pachycarpidine | BDBM50597716 | Oxymatrine | BBL030371 | MLS001215101 | rel-(41S, 7aS, 13aR, 13bR)-10-Oxohexadecahydrodipyrido[2, 1-f:3', 2', 1'-ij][1, 6]naphthyridine 4-oxide | Matrine 1beta-oxide | Ammothamnine | SCHEMBL13394285 | Oxysophoridine | DTXSID409374

Specifications & Purity

≥98%(HPLC)

Storage

Store at 2-8°C, Protected from light, Argon charged

Shipped In

Wet ice

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

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: C1CC2C3CCC[N+]4(C3C(CCC4)CN2C(=O)C1)[O-]
• IUPAC Name: (1R,2R,9S,17S)-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• InChIKey: XVPBINOPNYFXID-LHDUFFHYSA-N
• INCHI: 1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15-,17?/m0/s1
• Isomeric SMILES: C1C[C@@H]2[C@H]3CCC[N+]4([C@H]3[C@@H](CCC4)CN2C(=O)C1)[O-]
• Molecular Weight: 264.36
• Reaxy-Rn: 753307
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=753307&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Lupin alkaloids
      • Subclass Matrine alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Lupin alkaloids
• Subclass: Matrine alkaloids
• Intermediate Tree Nodes: Not available
• Direct Parent: Matrine alkaloids
• Alternative Parents: Quinolizidinones Naphthyridines Piperidinones Delta lactams Trialkyl amine oxides Tertiary carboxylic acid amides Trisubstituted amine oxides and derivatives Azacyclic compounds Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Matrine - Quinolizidinone - Diazanaphthalene - Naphthyridine - Quinolizidine - Delta-lactam - Piperidinone - Piperidine - Trialkyl amine oxide - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Organoheterocyclic compound - Azacycle - N-oxide - Carboxylic acid derivative - Trisubstituted n-oxide - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic zwitterion - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one skeleton.
• External Descriptors: Quinolizidine alkaloids

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)

MAOA Tclin Monoamine oxidase A (11911 Activities)

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HepG2 (196354 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Hepatitis B virus (7925 Activities)

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Coxsackievirus B3 (1096 Activities)

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Influenza A virus (11224 Activities)

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Enterovirus A71 (1246 Activities)

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MDCK (10148 Activities)

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Blood (6 Activities)

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Tgfbr1 TGF-beta receptor type-1 (52 Activities)

Discover Target: Tgfbr1

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light & air & heat sensitive
• Melt Point(°C): 206℃
• Molecular Weight: 264.360 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 264.184 Da
• Monoisotopic Mass: 264.184 Da
• Topological Polar Surface Area: 38.400 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 400.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

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13. Qiuyan Lin, Na Zheng, Qirui An, Zhifei Xiu, Xiaoqian Li, Huicheng Zhu, Changcheng Chen, Yunyang Li, Sujing Wang.  (2024)  Phthalate monoesters accumulation in residential indoor dust and influence factors.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:39047842] [10.1016/j.scitotenv.2024.174900]

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19. Juan Zhang, Zilin Chen.  (2013)  Determination of Matrine and Oxymatrine in Sophora Flavescens by Nonaqueous Capillary Electrophoresis-Electrospray Ionization-Ion Trap-Mass Spectrometry.  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2012.726684]

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