Cucurbitacin IIb - ≥98% , CAS No.50298-90-3

CAS: 50298-90-3 Cat. No.: C412645 Peso molecular: 520.71

GRADE & PURITY ≥98%

Synonyms

(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 | HY-N1987 | Curcurbitacin-Iib | Cucurbitacin centob | S0949 |

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

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,

Specifications

Sinónimos

(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 | HY-N1987 | Curcurbitacin-Iib | Cucurbitacin centob | S0949 |

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

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

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504765495
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765495
• Sonrisas canónicas: 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
• 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
• InChIKey: VVBWBGOEAVGFTN-LPQIEKFGSA-N
• 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
• Isómeros 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
• Peso molecular: 520.71
• Reaxy-Rn: 2685644
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2685644&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Cucurbitacins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

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

Objetivos asociados (humanos)

COLO 205 (50209 Activities)

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KB (17409 Activities)

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Objetivos asociados (no humanos)

Hepatitis B virus (7925 Activities)

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P388 (20296 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Solubility (25°C) In vitro
• Sensibilidad: light sensitive
• Peso molecular: 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

Referencias

1. Yinyin Zhao, Kangxiao Guo, Yongwang Yan, Binyuan Jiang.  (2024)  Cucurbitacin IIb alleviates colitis via regulating gut microbial composition and metabolites.  Heliyon,      [PMID:39347394] [10.1016/j.heliyon.2024.e38051]