(+)-Dehydroabietylamine [Optical Resolving Agent] - ≥90%(GC) , CAS No.1446-61-3

CAS: 1446-61-3 Cat. No.: D154779 Molecular Weight: 285.48 EC Number: 215-899-7

GRADE & PURITY ≥90%(GC)

Synonyms

EPA Pesticide Chemical Code 004206 | 13-Isopropylpodocarpa-8,11,13-trien-15-amine | Amine D | ((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanamine | Q15409408 | (+)-Dehydroabietylamine; >95% | Leelamine | W-10

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

Leelamine is an orally active pyruvate dehydrogenase kinase (PDK) inhibitor with an IC50 value of 9.5 μM, showing a blood glucose lowering effect in the diabetic mouse. Leelamine is also a weak agonist of cannabinoid receptors CB1 and CB2. Leelamine decreases mitotic activity, prostate-specific antigen expression and induces Apoptosis to cell death in cancer cells.

Specifications

Synonyms

EPA Pesticide Chemical Code 004206 | 13-Isopropylpodocarpa-8, 11, 13-trien-15-amine | Amine D | ((1R, 4aS, 10aR)-7-Isopropyl-1, 4a-dimethyl-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthren-1-yl)methanamine | Q15409408 | (+)-Dehydroabietylamine; >95% | Leelamine | W-10

Specifications & Purity

≥90%(GC)

Biochemical and Physiological Mechanisms

Pyruvate dehydrogenase kinase (PDK) inhibitor (IC 50 = 9.5 µM). It has weak affinity for human CB 1 and CB 2 receptors, exhibiting 20% displacement of [3H]-CP55940 at a concentration of 10 µM.

Storage

Protected from light, Room temperature

Shipped In

Normal

Action Type

AGONIST

Note

Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 6 months. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥90%(GC)

Names and Identifiers

• Pubchem Sid: 488183548
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183548
• Canonical Smiles: CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)CN)C
• IUPAC Name: [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
• InChIKey: JVVXZOOGOGPDRZ-SLFFLAALSA-N
• INCHI: 1S/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1
• Isomeric SMILES: CC(C)C1=CC2=C(C=C1)[C@]3(CCC[C@@]([C@@H]3CC2)(C)CN)C
• Molecular Weight: 285.48
• Reaxy-Rn: 2383194
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2383194&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: Diterpenoids
• Alternative Parents: Hydrophenanthrenes Tetralins Aralkylamines Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Diterpenoid - Abietane diterpenoid - Phenanthrene - Hydrophenanthrene - Tetralin - Aralkylamine - Benzenoid - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Primary aliphatic amine - Amine - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
• 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)

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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Homo sapiens (32628 Activities)

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5637 (630 Activities)

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EJ (302 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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SH-SY5Y (11521 Activities)

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SW-1736 (356 Activities)

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A549 (127892 Activities)

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FaDu (1726 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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A2780 (11979 Activities)

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HUVEC (11049 Activities)

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Jurkat (10389 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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GMNN Tbio Geminin (128009 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Mus musculus (284745 Activities)

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NIH3T3 (5395 Activities)

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L6 (7924 Activities)

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

Discover Target: Nfe2l2

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Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: 45° (C=4,MeOH)
• Melt Point(°C): 40 °C
• Molecular Weight: 285.500 g/mol
• XLogP3: 5.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 285.246 Da
• Monoisotopic Mass: 285.246 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 376.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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. Shiyu Wu, Yufu Yi, Shengliang Liao, Hongyan Si, Yuling Yang, Guorong Fan, Peng Wang.  (2021)  Synthesis and Shape-Selective Catalytic Application of Ordered Cubic Ia3̅d Supermicroporous Materials Templated by Rosin-Derived Quaternary Ammonium Salt with a Hydroxyl Radical in the Headgroup.  LANGMUIR,      [PMID:33397112] [10.1021/acs.langmuir.0c03356]

2. Xiaoyun Liu, Ruhong Zhang, Tianquan Li, Pengfei Zhu, Qixin Zhuang.  (2017)  Novel Fully Biobased Benzoxazines from Rosin: Synthesis and Properties.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.7b02650]