Deoxyandrographolide - Moligand™,≥98% , CAS No.4176-97-0

CAS: 4176-97-0 Cat. No.: D303686 Molecular Weight: 334.45

GRADE & PURITY Moligand™, ≥98%

Synonyms

2(5H)-Furanone, 3-(2-((1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)- | 3-[2-[(1R,4abeta)-2-Methylene-5alpha-(hydroxymethyl)-5,8aalpha-dimethyl-6alpha-hydroxydecalin-1alpha-yl]ethyl]-2,5-dihydrofur

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

14-Deoxyandrographolide is a diterpene with calcium channel blocking activity and acts as a uterine smooth muscle relaxant. 14-Deoxyandrographolide stimulates the release of nitric oxide (NO) in endothelial cells. 14-Deoxyandrographolide gradually desensitizes liver cells to TNF-α mediated apoptosis by inducing the release of TNFRSF1A.

Specifications

Synonyms

2(5H)-Furanone, 3-(2-((1R, 4aS, 5R, 6R, 8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5, 8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)- | 3-[2-[(1R, 4abeta)-2-Methylene-5alpha-(hydroxymethyl)-5, 8aalpha-dimethyl-6alpha-hydroxydecalin-1alpha-yl]ethyl]-2, 5-dihydrofur

Specifications & Purity

Moligand™, ≥98%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC12CCC(C(C1CCC(=C)C2CCC3=CCOC3=O)(C)CO)O
• IUPAC Name: 4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• InChIKey: GVRNTWSGBWPJGS-YSDSKTICSA-N
• INCHI: 1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1
• Isomeric SMILES: C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)(C)CO)O
• Molecular Weight: 334.45
• Reaxy-Rn: 47358493
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=47358493&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpene lactones
• Alternative Parents: Colensane and clerodane diterpenoids Butenolides Enoate esters Secondary alcohols Lactones Cyclic alcohols and derivatives Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Diterpene lactone - Diterpenoid - Clerodane diterpenoid - 2-furanone - Cyclic alcohol - Dihydrofuran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Lactone - Secondary alcohol - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organooxygen compound - Primary alcohol - Organic oxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
• 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)

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

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A498 (42825 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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MCF7 (126967 Activities)

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SK-OV-3 (52876 Activities)

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U-251 (51189 Activities)

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NCI/ADR-RES (33767 Activities)

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MDA-MB-231 (73002 Activities)

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NCI-H522 (44358 Activities)

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SW-620 (52400 Activities)

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Associated Targets(non-human)

Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Candida albicans (78123 Activities)

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Rattus norvegicus (775804 Activities)

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PC-12 (7051 Activities)

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RAW264.7 (28094 Activities)

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BV-2 (3710 Activities)

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NIH3T3 (5395 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light & Moisture sensitive
• Boil Point(°C): 509.5±50.0℃ at 760 mmHg
• Melt Point(°C): 176-178℃
• Molecular Weight: 334.400 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.214 Da
• Monoisotopic Mass: 334.214 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 566.000
• 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