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Gamabufotalin (Standard)

CAT: 0804-HY-N0883RSize: 1 EachDry Ice: NoHazardous: No
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Description
Gamabufotalin (Gamabufagin), a main active compound isolated from Chinese medicine Chansu, has been shown to strongly inhibit cancer cell growth and inflammatory response. Gamabufotalin could inhibite angiogenesis by inhibiting the activation of VEGFR-2 signaling pathways.
CAS Number
465-11-2
Product Name Alternative
Gamabufagin (Standard)
UNSPSC
12352005
Target
VEGFR
Related Pathways
Protein Tyrosine Kinase/RTK
Field of Research
Cancer
Smiles
C[C@]([C@@H](C(C=C1)=COC1=O)CC2)(C[C@@H](O)[C@@]3([H])[C@@]4([H])CC[C@@]5([H])[C@@]3(CC[C@H](O)C5)C)[C@]24O
Molecular Formula
C24H34O5
Molecular Weight
402.52
References & Citations
[1]Yu Z, et al. Gamabufotalin, a bufadienolide compound from toad venom, suppresses COX-2 expression through targeting IKKβ/NF-κB signaling pathway in lung cancer cells. Mol Cancer. 2014 Aug 31;13:203.|[2]Dong Y, et al. Bufadienolide compounds sensitize human breast cancer cells to TRAIL-induced apoptosis via inhibition of STAT3/Mcl-1 pathway. Apoptosis. 2011 Apr;16 (4) :394-403.|[3]Lan YL, et al. Gamabufotalin induces a negative feedback loop connecting ATP1A3 expression and the AQP4 pathway to promote temozolomide sensitivity in glioblastoma cells by targeting the amino acid Thr794. Cell Prolif. 2020;53 (1) :e12732.|[4]Tang N, et al. Gamabufotalin, a major derivative of bufadienolide, inhibits VEGF-induced angiogenesis by suppressing VEGFR-2 signaling pathway. Oncotarget. 2016;7 (3) :3533-3547.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Gamabufotalin

Gamabufogenin is a steroid lactone. It is functionally related to a bufanolide.

CAS Number465-11-2
PubChem CID259803
IUPAC Name5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Molecular FormulaC24H34O5
Molecular Weight402.5
XLogP2
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count29
Formal Charge0
Complexity773
SMILES
C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)O
InChI
InChI=1S/C24H34O5/c1-22-9-7-16(25)11-15(22)4-5-18-21(22)19(26)12-23(2)17(8-10-24(18,23)28)14-3-6-20(27)29-13-14/h3,6,13,15-19,21,25-26,28H,4-5,7-12H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24+/m1/s1
InChIKey
FMTLOAVOGWSPEF-KJRPADTMSA-N
Chemical Structure
2D Structure
2D structure of Gamabufotalin
CAS: 465-11-2
CID: 259803
Formula: C24H34O5
MW: 402.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.5
XLogP32
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass402.24062418
Monoisotopic Mass402.24062418
Topological Polar Surface Area87 Ų
Heavy Atom Count29
Formal Charge0
Complexity773
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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