(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: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^3,^1^1.0^4,^9.0^1^5,^1^9]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[11.7.0.0^3,^1^1.0^4,^9.0^1^5,^1^9]icosa-3(11),4,6,8-tetraene-14,20-dione
• Synonyms: FTC; Fumitremorgin C

Database IDs

• CAS Number: 118974-02-0
• MDL Number: MFCD08702652
• PubChem SID: 162248033; 24724486
• PubChem CID: 403923

CALCULATED PROPERTIES

• Acid pKa: 15.106837
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.1129622
• LogD (pH = 7.4): 2.1129622
• Log P: 2.1129622
• Molar Refractivity: 106.5698 cm^3
• Polarizability: 41.968166 Å^3
• Polar Surface Area: 65.64 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble5 mg/mL; chloroform: soluble; DMSO: soluble; methanol: soluble5 mg/mL
• Apperance: film

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >98% (HPLC and TLC)
• Biological Source: from Neosartorya fischeri
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C22H25N3O3

DETAILS

Sigma Aldrich - F9054

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.