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Fumitremorgin C

CAT: 0804-HY-N2143-01Size: 250 µgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2143-01Size:250 µg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Fumitremorgin C is a potent and selective ABCG2/BRCP inhibitor.
CAS Number
118974-02-0
Product Name Alternative
12α-Fumitremorgin C
UNSPSC
12352005
Target
Antibiotic; Bacterial; BCRP
Type
Natural Products
Related Pathways
Anti-infection; Membrane Transporter/Ion Channel
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/Fumitremorgin_C.html
Purity
99.90
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C([C@]1([H])CC2=C([C@H](/C=C(C)\C)N13)NC4=C2C=CC(OC)=C4)N5[C@](CCC5)([H])C3=O
Molecular Formula
C22H25N3O3
Molecular Weight
379.45
References & Citations
[1]Rabindran SK, et al. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res. 1998 Dec 15;58 (24) :5850-8.|[2]Rabindran SK, et al. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 2000 Jan 1;60 (1) :47-50.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Fumitremorgin C

Fumitremorgin C is an organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter. It has a role as a mycotoxin and a breast cancer resistance protein inhibitor. It is an aromatic ether, an organic heteropentacyclic compound and an indole alkaloid.

CAS Number118974-02-0
PubChem CID403923
IUPAC Name(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione
Molecular FormulaC22H25N3O3
Molecular Weight379.5
XLogP3
Topological Polar Surface Area65.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Heavy Atom Count28
Formal Charge0
Complexity703
SMILES
CC(=C[C@H]1C2=C(C[C@@H]3N1C(=O)[C@@H]4CCCN4C3=O)C5=C(N2)C=C(C=C5)OC)C
InChI
InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
InChIKey
DBEYVIGIPJSTOR-FHWLQOOXSA-N
Chemical Structure
2D Structure
2D structure of Fumitremorgin C
CAS: 118974-02-0
CID: 403923
Formula: C22H25N3O3
MW: 379.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight379.5
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass379.18959167
Monoisotopic Mass379.18959167
Topological Polar Surface Area65.6 Ų
Heavy Atom Count28
Formal Charge0
Complexity703
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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