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118974-02-0 molecular structure
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(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione

ChemBase ID: 153894
Molecular Formular: C22H25N3O3
Molecular Mass: 379.4522
Monoisotopic Mass: 379.18959168
SMILES and InChIs

SMILES:
CC(=C[C@H]1c2c(c3ccc(cc3[nH]2)OC)C[C@@H]2N1C(=O)[C@@H]1CCCN1C2=O)C
Canonical SMILES:
COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
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

Cite this record

CBID:153894 http://www.chembase.cn/molecule-153894.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione
IUPAC Traditional name
(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione
Synonyms
FTC
Fumitremorgin C
CAS Number
118974-02-0
MDL Number
MFCD08702652
PubChem SID
162248033
24724486
PubChem CID
403923

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
F9054 external link Add to cart Please log in.
Data Source Data ID
PubChem 403923 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.106837  H Acceptors
H Donor LogD (pH = 5.5) 2.1129622 
LogD (pH = 7.4) 2.1129622  Log P 2.1129622 
Molar Refractivity 106.5698 cm3 Polarizability 41.968166 Å3
Polar Surface Area 65.64 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
acetonitrile: soluble5 mg/mL expand Show data source
chloroform: soluble expand Show data source
DMSO: soluble expand Show data source
methanol: soluble5 mg/mL expand Show data source
Apperance
film expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
>98% (HPLC and TLC) expand Show data source
Biological Source
from Neosartorya fischeri expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C22H25N3O3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - F9054 external link
Packaging
Store desiccated at 2-8 °C. Under these conditions, the product is stable for 2 years. A solution in DMSO is stable for 2 months at 2-8 °C.
Biochem/physiol Actions
Fumitremorgin C (FTC) is a fungal toxin of the diketopiperazines family of compounds. In mammalian cells, FTC is tremorgenic and causes cell cycle arrest. Fumitremorgin C has been shown to reverse resistance to doxorubicin, mitoxantrane, and topotecan in non-Pgp (P-glyco-protein), non-MRP (multidrug resistance protein) multidrug-resistance (MDR) cells. This reversal of resistance is associated with an increase in drug accumulation. Fumitremorgin C is a specific, selective, and potent inhibitor at micromolar concentrations of the breast cancer resistant protein (BCRP/ABCG2), an ABC transporter associated with chemotherapy resistance. FTC, in combination with mitoxantrone, can be used for the detection of ABCG2 functional activity in several cell lines.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

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