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Cucurbitacin IIb - 10mM in DMSO, high purity , CAS No.50298-90-3

    Grade & Purity:
  • 10mM in DMSO
In stock
Item Number
C424330
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C424330-1ml
1ml
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$241.90

IκB Selective Inhibitors

Basic Description

Synonyms Cucurbitacin IIb | 50298-90-3 | Dihydrocucurbitacin F | 23,24-Dihydrocucurbitacin F | (2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phen
Specifications & Purity 10mM in DMSO
Biochemical and Physiological Mechanisms Cucurbitacin IIb (CuIIb, Dihydrocucurbitacin F, 25-deacetyl hemslecin A) inhibits phosphorylation of STAT3, JNK and Erk1/2, enhances the phosphorylation of IκB and NF-κB, blocks nuclear translocation of NF-κB and decreases mRNA levels of IκBα and TNF-α. C
Storage Temp Protected from light,Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description

Information

Cucurbitacin IIb (CuIIb, Dihydrocucurbitacin F, 25-deacetyl hemslecin A) inhibits phosphorylation ofSTAT3,JNKandErk1/2, enhances the phosphorylation ofIκBandNF-κB, blocks nuclear translocation ofNF-κBand decreases mRNA levels ofIκBαandTNF-α. Cucurbitacin IIb exhibits anti-inflammatory activity and inducesapoptosis. Cucurbitacin IIb is isolated fromHemsleya amabilis.

Targets

STAT3 ; JNK ; ERK1/2 ; IκBα ; NF-κB 33577,

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Steroids and steroid derivatives
Subclass Cucurbitacins
Intermediate Tree Nodes Not available
Direct Parent Cucurbitacins
Alternative Parents Triterpenoids  3-hydroxy delta-5-steroids  3-alpha-hydroxysteroids  16-alpha-hydroxysteroids  14-alpha-methylsteroids  11-oxosteroids  Delta-5-steroids  Acyloins  Tertiary alcohols  Alpha-hydroxy ketones  Secondary alcohols  Cyclic alcohols and derivatives  Polyols  Organic oxides  Hydrocarbon derivatives  
Molecular Framework Aliphatic homopolycyclic compounds
Substituents Cucurbitacin skeleton - Triterpenoid - 25-hydroxysteroid - 22-oxosteroid - 21-oxosteroid - 20-hydroxysteroid - 3-alpha-hydroxysteroid - 16-hydroxysteroid - 16-alpha-hydroxysteroid - 14-alpha-methylsteroid - 3-hydroxysteroid - Oxosteroid - Hydroxysteroid - 11-oxosteroid - 2-hydroxysteroid - 3-hydroxy-delta-5-steroid - Delta-5-steroid - Acyloin - Alpha-hydroxy ketone - Tertiary alcohol - Cyclic alcohol - Secondary alcohol - Ketone - Polyol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Aliphatic homopolycyclic compound
Description This compound belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.
External Descriptors Not available

Associated Targets(Human)

COLO 205 (50209 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KB (17409 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Hepatitis B virus (7925 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
P388 (20296 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
INCHI InChI=1S/C30H48O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,17-20,23-24,31-32,35-37H,10-15H2,1-8H3/t17-,18+,19-,20+,23+,24-,27+,28-,29+,30+/m1/s1
InChIKey VVBWBGOEAVGFTN-LPQIEKFGSA-N
Smiles CC1(C(C(CC2C1=CCC3C2(C(=O)CC4(C3(CC(C4C(C)(C(=O)CCC(C)(C)O)O)O)C)C)C)O)O)C
Isomeric SMILES C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H]([C@H](C4(C)C)O)O)C)C)[C@](C)(C(=O)CCC(C)(C)O)O)O
Molecular Weight 520.71
Reaxy-Rn 2685644
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2685644&ln=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Sensitivity light sensitive
Molecular Weight 520.700 g/mol
XLogP3 2.000
Hydrogen Bond Donor Count 5
Hydrogen Bond Acceptor Count 7
Rotatable Bond Count 5
Exact Mass 520.34 Da
Monoisotopic Mass 520.34 Da
Topological Polar Surface Area 135.000 Ų
Heavy Atom Count 37
Formal Charge 0
Complexity 1020.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 10
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

Citations of This Product

1. Yinyin Zhao, Kangxiao Guo, Yongwang Yan, Binyuan Jiang.  (2024)  Cucurbitacin IIb alleviates colitis via regulating gut microbial composition and metabolites.  Heliyon,  10   

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