IUPAC/Chemical Name
Benzamide, N-(4,7-dihydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)-
InChi Key
NMCFFEJWADWZTI-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H21NO6/c1-11(2)4-5-13-10-14(6-8-17(13)25)21(27)23-18-19(26)15-7-9-16(24)12(3)20(15)29-22(18)28/h4,6-10,24-26H,5H2,1-3H3,(H,23,27)
SMILES Code
O=C(NC1=C(O)C2=CC=C(O)C(C)=C2OC1=O)C3=CC=C(O)C(C/C=C(C)\C)=C3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
395.41
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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2: Kominek LA, Meyer HF. Novobiocic acid synthetase. Methods Enzymol. 1975;43:502-8. doi: 10.1016/0076-6879(75)43111-1. PMID: 237214.
3: Rappa G, Shyam K, Lorico A, Fodstad O, Sartorelli AC. Structure-activity studies of novobiocin analogs as modulators of the cytotoxicity of etoposide (VP-16). Oncol Res. 2000;12(3):113-9. doi: 10.3727/096504001108747585. PMID: 11216669.
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5: Walsh CT, Losey HC, Freel Meyers CL. Antibiotic glycosyltransferases. Biochem Soc Trans. 2003 Jun;31(Pt 3):487-92. doi: 10.1042/bst0310487. PMID: 12773141.
6: Pacholec M, Tao J, Walsh CT. CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis. Biochemistry. 2005 Nov 15;44(45):14969-76. doi: 10.1021/bi051599o. PMID: 16274243.
7: Williams GJ, Goff RD, Zhang C, Thorson JS. Optimizing glycosyltransferase specificity via "hot spot" saturation mutagenesis presents a catalyst for novobiocin glycorandomization. Chem Biol. 2008 Apr;15(4):393-401. doi: 10.1016/j.chembiol.2008.02.017. PMID: 18420146; PMCID: PMC2813856.
8: Reusser F, Dolak LA. Novenamine is the active moiety in novobiocin. J Antibiot (Tokyo). 1986 Feb;39(2):272-4. PMID: 3007416.
9: Pi N, Meyers CL, Pacholec M, Walsh CT, Leary JA. Mass spectrometric characterization of a three-enzyme tandem reaction for assembly and modification of the novobiocin skeleton. Proc Natl Acad Sci U S A. 2004 Jul 6;101(27):10036-41. doi: 10.1073/pnas.0403526101. Epub 2004 Jun 24. PMID: 15218104; PMCID: PMC454160.
10: Sebek OK, Dolak LA. Microbial hydroxylation of novobiocin and related compounds. J Antibiot (Tokyo). 1984 Feb;37(2):136-42. doi: 10.7164/antibiotics.37.136. PMID: 6706850.
11: Steffensky M, Mühlenweg A, Wang ZX, Li SM, Heide L. Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891. Antimicrob Agents Chemother. 2000 May;44(5):1214-22. doi: 10.1128/aac.44.5.1214-1222.2000. PMID: 10770754; PMCID: PMC89847.
