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Hellebrigenin

CAT: 0931-TN1728-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0931-TN1728-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
465-90-7
Target
ERK, JNK, Apoptosis, p38 MAPK, PARP, Caspase, IAP
Related Pathways
Proteases/Proteasome, Apoptosis, MAPK, DNA Damage/DNA Repair, Chromatin/Epigenetic
Purity
0.9998
Bioactivity
Hellebrigenin, as a selective inhibitor of MAPK signaling pathways (ERK, p38, JNK) and XIAP, effectively suppresses Akt expression and phosphorylation. This compound activates endogenous apoptosis pathways (including mitochondrial membrane potential disruption, Caspase family activation, and PARP cleavage) while modulating apoptosis-related protein expression. Hellebrigenin also induces DNA double-strand breaks to activate the ATM pathway, inhibiting tumor cell proliferation and clonogenesis, primarily applied in research of oral squamous cell carcinoma and liver cancer.
Smiles
C(=O)[C@@]12[C@@]3([C@]([C@]4(O)[C@](C)(CC3)[C@H](CC4)C=5C=CC(=O)OC5)(CC[C@]1(O)C[C@@H](O)CC2)[H])[H]
Molecular Formula
C24H32O6
Molecular Weight
416.51
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Hellebrigenin

Hellebrigenin is a steroid aldehyde, a steroid lactone, a 3beta-hydroxy steroid, a 14beta-hydroxy steroid, a 19-oxo steroid and a 5beta-hydroxy steroid. It has a role as an autophagy inducer, an antineoplastic agent, an apoptosis inducer, an antileishmanial agent, an animal metabolite and a plant metabolite. It is functionally related to a 5beta-bufanolide.

CAS Number465-90-7
PubChem CID259577
IUPAC Name(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Molecular FormulaC24H32O6
Molecular Weight416.5
XLogP1.2
Topological Polar Surface Area104
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Heavy Atom Count30
Formal Charge0
Complexity834
SMILES
C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=COC(=O)C=C4)O)CC[C@]5([C@@]3(CC[C@@H](C5)O)C=O)O
InChI
InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1
InChIKey
TVKPTWJPKVSGJB-XHCIOXAKSA-N
Chemical Structure
2D Structure
2D structure of Hellebrigenin
CAS: 465-90-7
CID: 259577
Formula: C24H32O6
MW: 416.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight416.5
XLogP31.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass416.21988874
Monoisotopic Mass416.21988874
Topological Polar Surface Area104 Ų
Heavy Atom Count30
Formal Charge0
Complexity834
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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