Synonym
Neoaureothin, NSC 260179, Spectinabilin
IUPAC/Chemical Name
2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrien-1-ylidene]-2-furanyl]-4H-pyran-4-one
InChi Key
IZICQJAGBLBAMJ-QDYRYYKCSA-N
InChi Code
InChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-14,25H,15-16H2,1-6H3/b17-11+,18-13+,19-12+,23-14-/t25-/m1/s1
SMILES Code
CC(/C=C1CO[C@@H](C(OC(OC)=C2C)=C(C)C2=O)C\1)=C\C(C)=C\C(C)=C\C3=CC=C([N+]([O-])=O)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
Biological target:
Neoaureothin is a bacterial metabolite and androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
477.56
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 |
Formulation protocol:
TBD
1. Kawamura, T., Fujimaki, T., Hamanaka, N., et al. Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. J. Antibiot. (Tokyo) 63(10), 601-605 (2010).
2. Liu, C.X., Liu, S.H., Zhao, J.W., et al. A new spectinabilin derivative with cytotoxic activity from ant-derived Streptomyces sp. 1H-GS5. J. Asian Nat. Prod. Res. 19(9), 924-929 (2017).
3. Liu, M.J., Hwang, B.S., Jin, C.Z., et al. Screening, isolation and evaluation of a nematicidal compound from actinomycetes against the pine wood nematode, Bursaphelenchus xylophilus. Pest. Manag. Sci. 75(6), 1585-1593 (2019).
