Synonym
Amauromine; Antibiotic FR 900220; WF 6237; WF6237; WF-6237
IUPAC/Chemical Name
(1S,4S,12R,14S,17S,25R)-12,25-bis(2-methylbut-3-en-2-yl)-3,5,16,18-tetrazaheptacyclo[14.10.0.03,14.04,12.06,11.017,25.019,24]hexacosa-6,8,10,19,21,23-hexaene-2,15-dione
InChi Key
VKEAHNPKYMHYJJ-CBYNOBLXSA-N
InChi Code
InChI=1S/C32H36N4O2/c1-7-29(3,4)31-17-23-25(37)36-24(26(38)35(23)27(31)33-21-15-11-9-13-19(21)31)18-32(30(5,6)8-2)20-14-10-12-16-22(20)34-28(32)36/h7-16,23-24,27-28,33-34H,1-2,17-18H2,3-6H3/t23-,24-,27-,28-,31+,32+/m0/s1
SMILES Code
O=C(N1[C@]2([H])NC3=CC=CC=C3[C@]2(C(C=C)(C)C)C[C@@]41[H])[C@]5([H])C[C@@]6(C(C=C)(C)C)C7=CC=CC=C7N[C@@]6([H])N5C4=O
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
508.67
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 |
1: Nazir M, Harms H, Loef I, Kehraus S, El Maddah F, Arslan I, Rempel V, Müller CE, König GM. GPR18 Inhibiting Amauromine and the Novel Triterpene Glycoside Auxarthonoside from the Sponge-Derived Fungus Auxarthron reticulatum. Planta Med. 2015 Aug;81(12-13):1141-5. doi: 10.1055/s-0035-1545979. Epub 2015 May 8. PubMed PMID: 26287693.
2: Hakamata H, Sato S, Ueda H, Tokuyama H. AgNTf(2)-Mediated Allylation with Allylsilanes at C3a-Position of Hexahydropyrroloindoles: Application to Total Syntheses of Amauromine Alkaloids. Org Lett. 2017 Oct 6;19(19):5308-5311. doi: 10.1021/acs.orglett.7b02602. Epub 2017 Sep 19. PubMed PMID: 28926277.
3: Shan WG, Wu ZY, Pang WW, Ma LF, Ying YM, Zhan ZJ. α-Glucosidase Inhibitors from the Fungus Aspergillus terreus 3.05358. Chem Biodivers. 2015 Nov;12(11):1718-24. doi: 10.1002/cbdv.201500027. PubMed PMID: 26567949.
4: Müller JM, Stark CB. Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine. Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4798-802. doi: 10.1002/anie.201509468. Epub 2016 Mar 11. PubMed PMID: 26969898.
5: Takase S, Iwami M, Ando T, Okamoto M, Yoshida K, Horiai H, Kohsaka M, Aoki H, Imanaka H. Amauromine, a new vasodilator. Taxonomy, isolation and characterization. J Antibiot (Tokyo). 1984 Nov;37(11):1320-23. PubMed PMID: 6511659.
6: Elsebai MF, Rempel V, Schnakenburg G, Kehraus S, Müller CE, König GM. Identification of a Potent and Selective Cannabinoid CB1 Receptor Antagonist from Auxarthron reticulatum. ACS Med Chem Lett. 2011 Sep 17;2(11):866-9. doi: 10.1021/ml200183z. eCollection 2011 Nov 10. PubMed PMID: 24900275; PubMed Central PMCID: PMC4017988.
7: Ishikawa K, Hosoe T, Itabashi T, Wakana D, Takizawa K, Yaguchi T, Kawai K. Novoamauromine and ent-Cycloechinulin: two new diketopiperazine derivatives from Aspergillus novofumigatus. Chem Pharm Bull (Tokyo). 2010 May;58(5):717-9. PubMed PMID: 20460802.
