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Bufalin - 10mM in DMSO, high purity , CAS No.465-21-4

    Grade & Purity:
  • 10mM in DMSO
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Item Number
B424094
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B424094-1ml
1ml
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$60.90

Selective Na + /K + -ATPase inhibitor. Potent steroid receptor coactivators SRC-3 and SRC-1 inhibitor.

Basic Description

Synonyms 3-methoxy-2-pyridinone | Bufalin: Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-, | bufalin | Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)- | UNII-U549S98QLW | (3beta,5beta,10alpha,17alpha)-3,14-dihydroxybufa-20,22-dienolide | BRD-K63606607-001-02-6 |
Specifications & Purity 10mM in DMSO
Biochemical and Physiological Mechanisms Na + /K + -ATPase inhibitor. Potent steroid receptor coactivators SRC-3 and SRC-1 inhibitor. Induces cell differentiation and apoptosis. Activates AP-1 via JNK. Shows antitumor effects in vivo.
Storage Temp 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

Bufalin is a C-24 steroid with an α-pyrone ring positioned at C-17. It is present in the venom glands and skin of toad, Venenum Bufonis.Bufalin is a cardiotonic steroid[5] and is digoxin-like component of Chan Su.
Bufalin has been used:
• to test its effect on invasion and activation of nuclear factor kappa- B (NF-κB) cells and tumor necrosis factor-α (TNF-α) stimulated rheumatoid arthritis fibroblast-like synoviocytes (RAFLSs)
• as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytes
• to test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Steroids and steroid derivatives
Subclass Steroid lactones
Intermediate Tree Nodes Not available
Direct Parent Bufanolides and derivatives
Alternative Parents 3-beta-hydroxysteroids  14-hydroxysteroids  Pyranones and derivatives  Tertiary alcohols  Heteroaromatic compounds  Secondary alcohols  Lactones  Cyclic alcohols and derivatives  Oxacyclic compounds  Organic oxides  Hydrocarbon derivatives  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents Bufanolide-skeleton - 3-hydroxysteroid - 14-hydroxysteroid - Hydroxysteroid - 3-beta-hydroxysteroid - Pyranone - Pyran - Tertiary alcohol - Heteroaromatic compound - Cyclic alcohol - Secondary alcohol - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Alcohol - Aromatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
External Descriptors Bufanolides and derivatives

Associated Targets(Human)

AR Tclin Androgen Receptor (11781 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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CYP3A5 Tclin Cytochrome P450 3A5 (525 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BGC-823 (3035 Activities)
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BT-474 (2113 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BXPC-3 (2997 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Daudi (625 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DU-145 (51482 Activities)
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HL-60 (67320 Activities)
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HT-1080 (3966 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LoVo (4724 Activities)
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MCF7 (126967 Activities)
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MDA-MB-468 (9477 Activities)
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MES-SA (905 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MES-SA/Dx5 (643 Activities)
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NCI-H1975 (4994 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MRC5 (9203 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NCI-N87 (850 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PANC-1 (6144 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-OV-3 (52876 Activities)
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THP-1 (11052 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
U-87 MG (3946 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
786-0 (47912 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A549 (127892 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Bel-7402 (4577 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HepG2 (196354 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HUVEC (11049 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
HeLa (62764 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MV4-11 (7307 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ATP1A1 Tclin Sodium/potassium-transporting ATPase (386 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CLCN3 Tchem H(+)/Cl(-) exchange transporter 3 (23 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A7 Tclin Cytochrome P450 3A7 (35 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

CCRF S-180 (1031 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MH60 (82 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
H22 (575 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BCHE Cholinesterase (8742 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 5-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-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
INCHI InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
InChIKey QEEBRPGZBVVINN-BMPKRDENSA-N
Smiles CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=COC(=O)C=C5)O)C)O
Isomeric SMILES C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O
WGK Germany 3
RTECS EI2962500
Molecular Weight 386.52
Reaxy-Rn 21842605
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21842605&ln=

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

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

Chemical and Physical Properties

Molecular Weight 386.500 g/mol
XLogP3 3.200
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 1
Exact Mass 386.246 Da
Monoisotopic Mass 386.246 Da
Topological Polar Surface Area 66.800 Ų
Heavy Atom Count 28
Formal Charge 0
Complexity 741.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 8
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

Solution Calculators

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