MedKoo Cat#: 463454 | Name: Heronapyrrole B

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Heronapyrrole B is a farnesylated 2-nitropyrrole bacterial metabolite that has been found in Streptomyces and has antibacterial activity. It is active against the Gram-positive bacteria S. aureus and B. subtilis but not Gram-negative P. aeruginosa or E. coli.

Chemical Structure

Heronapyrrole B
Heronapyrrole B
CAS#1255704-24-5

Theoretical Analysis

MedKoo Cat#: 463454

Name: Heronapyrrole B

CAS#: 1255704-24-5

Chemical Formula: C19H32N2O6

Exact Mass: 384.2260

Molecular Weight: 384.47

Elemental Analysis: C, 59.36; H, 8.39; N, 7.29; O, 24.97

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Synonym
Heronapyrrole B; Heronapyrrole-B; (+)-Heronapyrrole B;
IUPAC/Chemical Name
(2R,3S,10S,E)-3,7,11-trimethyl-1-(5-nitro-1H-pyrrol-3-yl)dodec-6-ene-2,3,10,11-tetraol
InChi Key
IQLMWMXFFNAONP-WJEGLXPMSA-N
InChi Code
InChI=1S/C19H32N2O6/c1-13(7-8-15(22)18(2,3)24)6-5-9-19(4,25)16(23)10-14-11-17(20-12-14)21(26)27/h6,11-12,15-16,20,22-25H,5,7-10H2,1-4H3/b13-6+/t15-,16+,19-/m0/s1
SMILES Code
CC(O)([C@H](CC/C(C)=C/CC[C@](O)([C@@H](CC1=CNC([N+]([O-])=O)=C1)O)C)O)C
Appearance
Solid powder
Purity
>95% (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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 384.47 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.

Recalculate based on batch purity %
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
1: Ding XB, Brimble MA, Furkert DP. Reactivity of 2-Nitropyrrole Systems: Development of Improved Synthetic Approaches to Nitropyrrole Natural Products. J Org Chem. 2018 Oct 19;83(20):12460-12470. doi: 10.1021/acs.joc.8b01692. Epub 2018 Oct 10. PMID: 30270625. 2: Khalil ZG, Cruz-Morales P, Licona-Cassani C, Marcellin E, Capon RJ. Inter- Kingdom beach warfare: Microbial chemical communication activates natural chemical defences. ISME J. 2019 Jan;13(1):147-158. doi: 10.1038/s41396-018-0265-z. Epub 2018 Aug 16. PMID: 30116041; PMCID: PMC6299108. 3: Raju R, Piggott AM, Barrientos Diaz LX, Khalil Z, Capon RJ. Heronapyrroles A-C: farnesylated 2-nitropyrroles from an Australian marine-derived Streptomyces sp. Org Lett. 2010 Nov 19;12(22):5158-61. doi: 10.1021/ol102162d. Epub 2010 Oct 15. PMID: 20949971.