Acetylaranotin

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

MedKoo CAT#: 599064

CAS#: 20485-01-2

Description: Acetylaranotin belongs to one structural subgroup of ETPs characterized by the presence of a seven-membered 4,5-dihydrooxepine ring.


Chemical Structure

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Acetylaranotin
CAS# 20485-01-2

Theoretical Analysis

MedKoo Cat#: 599064
Name: Acetylaranotin
CAS#: 20485-01-2
Chemical Formula: C22H20N2O8S2
Exact Mass: 504.07
Molecular Weight: 504.520
Elemental Analysis: C, 52.37; H, 4.00; N, 5.55; O, 25.37; S, 12.71

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Acetylaranotin; Antibiotic LL-S-88-A; LL-S-88-A;

IUPAC/Chemical Name: (5S,5aR,7aR,13S,13aR,15aR)-7,15-dioxo-5,5a,13,13a-tetrahydro-7H,8H,15H,16H-7a,15a-epidithiooxepino[3',4':4,5]pyrrolo[1,2-a]oxepino[3',4':4,5]pyrrolo[1,2-d]pyrazine-5,13-diyl diacetate

InChi Key: OHTZNUUGYPDWEB-FJHDBJKYSA-N

InChi Code: InChI=1S/C22H20N2O8S2/c1-11(25)31-15-3-5-29-9-13-7-21-20(28)24-18-14(10-30-6-4-16(18)32-12(2)26)8-22(24,34-33-21)19(27)23(21)17(13)15/h3-6,9-10,15-18H,7-8H2,1-2H3/t15-,16-,17+,18+,21+,22+/m0/s1

SMILES Code: O=C([C@]1(SS2)C3)N([C@@]2(C4)C(N1[C@@H]5C3=COC=C[C@@H]5OC(C)=O)=O)[C@@H]6C4=COC=C[C@@H]6OC(C)=O

Appearance: Solid powder

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 504.52 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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3: Belov DS, Ratmanova NK, Andreev IA, Kurkin AV. Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: formal synthesis of (±)-acetylaranotin. Chemistry. 2015 Mar 2;21(10):4141-7. doi: 10.1002/chem.201405811. Epub 2015 Jan 28. PubMed PMID: 25631763.

4: Codelli JA, Puchlopek AL, Reisman SE. Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine. J Am Chem Soc. 2012 Feb 1;134(4):1930-3. doi: 10.1021/ja209354e. Epub 2011 Oct 28. PubMed PMID: 22023250; PubMed Central PMCID: PMC3271125.

5: Nagarajan R, Neuss N, Marsh MM. Aranotin and related metabolites. 3. Configuration and conformation of acetylaranotin. J Am Chem Soc. 1968 Nov 6;90(23):6518-9. PubMed PMID: 5682450.

6: Murdock KC. Antiviral agents. Chemical modifications of a disulfide antibiotic, acetylaranotin. J Med Chem. 1974 Aug;17(8):827-35. PubMed PMID: 4602597.

7: Choi EJ, Park JS, Kim YJ, Jung JH, Lee JK, Kwon HC, Yang HO. Apoptosis-inducing effect of diketopiperazine disulfides produced by Aspergillus sp. KMD 901 isolated from marine sediment on HCT116 colon cancer cell lines. J Appl Microbiol. 2011 Jan;110(1):304-13. doi: 10.1111/j.1365-2672.2010.04885.x. Epub 2010 Dec 2. PubMed PMID: 21122037.

8: Moncrief JW. Molecular structure of bisdethiodi(methylthio)acetylaranotin including absolute configuration. J Am Chem Soc. 1968 Nov 6;90(23):6517-8. PubMed PMID: 5682449.

9: Billard W, Peets E. Sulfhydryl reactivity: mechanism of action of several antiviral compounds--selenocystine, 4-(2-propinyloxy)-beta-nitrostyrene, and acetylaranotin. Antimicrob Agents Chemother. 1974 Jan;5(1):19-24. PubMed PMID: 4840446; PubMed Central PMCID: PMC428913.

10: Guo CJ, Wang CC. Recent advances in genome mining of secondary metabolites in Aspergillus terreus. Front Microbiol. 2014 Dec 23;5:717. doi: 10.3389/fmicb.2014.00717. eCollection 2014. Review. PubMed PMID: 25566227; PubMed Central PMCID: PMC4274970.

11: Haritakun R, Rachtawee P, Chanthaket R, Boonyuen N, Isaka M. Butyrolactones from the fungus Aspergillus terreus BCC 4651. Chem Pharm Bull (Tokyo). 2010 Nov;58(11):1545-8. PubMed PMID: 21048353.

12: Kawahara N, Nozawa K, Yamazaki M, Nakajima S, Kawai K. Structures of novel epipolythiodioxopiperazines, emethallicins B, C, and D, potent inhibitors of histamine release, from Emericella heterothallica. Chem Pharm Bull (Tokyo). 1990 Jan;38(1):73-8. PubMed PMID: 2337952.

13: Samson RA, Peterson SW, Frisvad JC, Varga J. New species in Aspergillus section Terrei. Stud Mycol. 2011 Jun 30;69(1):39-55. doi: 10.3114/sim.2011.69.04. PubMed PMID: 21892242; PubMed Central PMCID: PMC3161753.

14: Suzuki Y, Takahashi H, Esumi Y, Arie T, Morita T, Koshino H, Uzawa J, Uramoto M, Yamaguchi I. Haematocin, a new antifungal diketopiperazine produced by Nectria haematococca Berk. et Br. (880701a-1) causing nectria blight disease on ornamental plants. J Antibiot (Tokyo). 2000 Jan;53(1):45-9. PubMed PMID: 10724007.