Synonym
Austrocortirubin; (1S,3S)-Austrocortirubin; (5S,7S)-Austrocortirubin; (+)-Austrocortirubin; NSC-626307; NSC 626307; NSC626307;
IUPAC/Chemical Name
(1S-cis)-1,2,3,4-tetrahydro-1,3,5,8-tetrahydroxy-6-methoxy-3-methyl-9,10-anthracenedione
InChi Key
DGBJOTSGQUQQJO-ZKANADHPSA-N
InChi Code
InChI=1S/C16H16O7/c1-16(22)4-6-10(8(18)5-16)15(21)11-7(17)3-9(23-2)14(20)12(11)13(6)19/h3,8,17-18,20,22H,4-5H2,1-2H3/t8-,16+/m0/s1
SMILES Code
O=C1C2=C(C(O)=C(OC)C=C2O)C(C3=C1[C@@H](O)C[C@](C)(O)C3)=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
>2 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
320.29
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: Beattie KD, Ellwood N, Kumar R, Yang X, Healy PC, Choomuenwai V, Quinn RJ, Elliott AG, Huang JX, Chitty JL, Fraser JA, Cooper MA, Davis RA. Antibacterial and antifungal screening of natural products sourced from Australian fungi and characterisation of pestalactams D-F. Phytochemistry. 2016 Apr;124:79-85. doi: 10.1016/j.phytochem.2015.12.014. Epub 2015 Dec 29. PubMed PMID: 26743853.
2: Wang Y, Islam MA, Davis RA, McAlpine SR. The fungal natural product (1S,3S)-austrocortirubin induces DNA damage in HCT116 cells via a mechanism unique from other DNA damaging agents. Bioorg Med Chem Lett. 2015 Jan 15;25(2):249-53. doi: 10.1016/j.bmcl.2014.11.055. Epub 2014 Nov 29. PubMed PMID: 25499433.
3: Choomuenwai V, Andrews KT, Davis RA. Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold. Bioorg Med Chem. 2012 Dec 15;20(24):7167-74. doi: 10.1016/j.bmc.2012.09.052. Epub 2012 Oct 10. PubMed PMID: 23117170.
4: Beattie KD, Rouf R, Gander L, May TW, Ratkowsky D, Donner CD, Gill M, Grice ID, Tiralongo E. Antibacterial metabolites from Australian macrofungi from the genus Cortinarius. Phytochemistry. 2010 Jun;71(8-9):948-55. doi: 10.1016/j.phytochem.2010.03.016. Epub 2010 Apr 12. PubMed PMID: 20392467.
5: Elsworth C, Gill M, Saubern S. Biosynthesis of tetrahydroanthraquinones in fungi. Phytochemistry. 2000 Sep;55(1):23-7. PubMed PMID: 11021640.
