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MedKoo Cat#: 598878 | Name: Aranotin

Description:

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

Aranotin is an antiviral agent.

Chemical Structure

Aranotin
CAS#19885-51-9

Theoretical Analysis

MedKoo Cat#: 598878

Name: Aranotin

CAS#: 19885-51-9

Chemical Formula: C20H18N2O7S2

Exact Mass: 462.0555

Molecular Weight: 462.49

Elemental Analysis: C, 51.94; H, 3.92; N, 6.06; O, 24.22; S, 13.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Aranotin; Antibiotic A 21101-IL; L 53185; L-53185; L53185; Lilly 53185; 53183;
IUPAC/Chemical Name
(5S,5aS,7aR,13S,13aS,15aR)-13-hydroxy-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]pyrazin-5-yl acetate
InChi Key
HXWOWBFXYUFFKS-PSJNWGMYSA-N
InChi Code
InChI=1S/C20H18N2O7S2/c1-10(23)29-14-3-5-28-9-12-7-20-17(25)21-15-11(8-27-4-2-13(15)24)6-19(21,30-31-20)18(26)22(20)16(12)14/h2-5,8-9,13-16,24H,6-7H2,1H3/t13-,14-,15-,16-,19+,20+/m0/s1
SMILES Code
CC(O[C@H]1C=COC=C2C[C@@]34SS[C@@]5(C(N4[C@H]12)=O)CC6=COC=C[C@@H]([C@H]6N5C3=O)O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 462.49 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: Cameron A, Fisher B, Fisk N, Hummel J, White JM, Krenske EH, Rizzacasa MA. Towards the Synthesis of Dihydrooxepino[4,3-b]pyrrole-Containing Natural Products via Cope Rearrangement of Vinyl Pyrrole Epoxides. Org Lett. 2015 Dec 18;17(24):5998-6001. doi: 10.1021/acs.orglett.5b02965. Epub 2015 Dec 2. PubMed PMID: 26629727. 2: Gross U, Nieger M, Bräse S. A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin. Chemistry. 2010 Oct 11;16(38):11624-31. doi: 10.1002/chem.201001169. Epub 2010 Aug 31. PubMed PMID: 20809554. 3: Neuss N, Boeck LD, Brannon DR, Cline JC, DeLong DC, Gorman M, Huckstep LL, Lively DH, Mabe J, Marsh MM, Molloy BB, Nagarajan R, Nelson JD, Stark WM. Aranotin and related metabolites from Arachniotus aureus (Eidam) Schroeter. IV. Fermentation, isolation, structure elucidation, biosynthesis, and antiviral properties. Antimicrob Agents Chemother (Bethesda). 1968;8:213-9. PubMed PMID: 5735362. 4: 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. 5: Ohler E, Poisel H, Tataruch F, Schmidt U. [Studies in the synthesis of the antibiotics gliotoxin, sporidesmin, aranotin, and chaetocin. IV. Preparation of epidithio-L-prolyl-L-proline anhydride]. Chem Ber. 1972;105(2):635-41. German. PubMed PMID: 4645598. 6: Poisel H, Schmidt U. [Studies in the synthesis of the antibiotics Gliotoxin, sporidesmin, Aranotin, and chaetocin. 3. Introduction of alkyl groups and sulfur functions into the 3- and 6-positions of 2.5-dioxopiperazines by electrophilic substitutions]. Chem Ber. 1972;105(2):625-34. German. PubMed PMID: 4645597. 7: Ohler E, Tataruch F, Schmidt U. [Studies in the synthesis of the series of 3.6-epidithio-2,5-dioxo-piperazine antibiotics gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. V. Preparation of epitrithio- and epitetrathio-L-prolyl-L-proline anhydride]. Chem Ber. 1972;105(11):3658-61. German. PubMed PMID: 4637543. 8: Ohler E, Tataruch F, Schmidt U. [Amino acids and peptides. VII. Studies on the synthesis of 3,6-epidithio-2,5-dioxopiperazine antibiotics: gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. VII. The introduction of oxygen into prolyl-prolinanhydride via lead acetate: a new approach to the epidisulfide of prolyl-prolinanhydride]. Chem Ber. 1973;106(2):396-8. German. PubMed PMID: 4721259. 9: Ohler E, Tataruch F, Schmidt U. [Amino acids and peptides. VI. Synthesis of the 3,6-epidithio-2,5-dioxopiperazine antibiotics gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. VI. Nucleophilic introduction of sulfur functions via sulfones and hydroxy derivates of cyclic dipeptides (dioxopiperazines)]. Chem Ber. 1973;106(1):165-76. German. PubMed PMID: 4698552.

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