MedKoo Cat#: 593095 | Name: Averufin

Description:

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

Averufin is has antifungal activity.

Chemical Structure

Averufin
Averufin
CAS#14016-29-6

Theoretical Analysis

MedKoo Cat#: 593095

Name: Averufin

CAS#: 14016-29-6

Chemical Formula: C20H16O7

Exact Mass: 368.0896

Molecular Weight: 368.34

Elemental Analysis: C, 65.22; H, 4.38; O, 30.40

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
Averufin;
IUPAC/Chemical Name
2,6-Epoxy-2H-anthra(2,3-b)oxocin-8,13-dione, 3,4,5,6-tetrahydro-2-methyl-7,9,11-trihydroxy-
InChi Key
RYFFZJHGQCKWMV-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H16O7/c1-20-4-2-3-12(26-20)16-13(27-20)7-10-15(19(16)25)18(24)14-9(17(10)23)5-8(21)6-11(14)22/h5-7,12,21-22,25H,2-4H2,1H3
SMILES Code
O=C(C1=C2C=C(O)C=C1O)C3=C(C=C4OC(O5)(C)CCCC5C4=C3O)C2=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 368.34 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: Liu K, Zheng Y, Miao C, Xiong Z, Xu L, Guan H, Yang Y, Zhao L. The antifungal metabolites obtained from the rhizospheric Aspergillus sp. YIM PH30001 against pathogenic fungi of Panax notoginseng. Nat Prod Res. 2014;28(24):2334-7. doi: 10.1080/14786419.2014.935941. Epub 2014 Jul 15. PubMed PMID: 25022791. 2: Wu CJ, Li CW, Cui CB. Seven new and two known lipopeptides as well as five known polyketides: the activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate. Mar Drugs. 2014 Mar 28;12(4):1815-38. doi: 10.3390/md12041815. PubMed PMID: 24686557; PubMed Central PMCID: PMC4012460. 3: Shao C, Wang C, Wei M, Li S, She Z, Gu Y, Lin Y. Structural and spectral assignments of six anthraquinone derivatives from the mangrove fungus (ZSUH-36). Magn Reson Chem. 2008 Sep;46(9):886-9. doi: 10.1002/mrc.2266. PubMed PMID: 18615624. 4: Sakuno E, Kameyama M, Nakajima H, Yabe K. Purification and gene cloning of a dehydrogenase from Lactobacillus brevis that catalyzes a reaction involved in aflatoxin biosynthesis. Biosci Biotechnol Biochem. 2008 Mar;72(3):724-34. Epub 2008 Mar 7. PubMed PMID: 18323645. 5: Shier WT, Lao Y, Steele TW, Abbas HK. Yellow pigments used in rapid identification of aflatoxin-producing Aspergillus strains are anthraquinones associated with the aflatoxin biosynthetic pathway. Bioorg Chem. 2005 Dec;33(6):426-38. Epub 2005 Nov 2. PubMed PMID: 16260026. 6: Wen Y, Hatabayashi H, Arai H, Kitamoto HK, Yabe K. Function of the cypX and moxY genes in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol. 2005 Jun;71(6):3192-8. PubMed PMID: 15933021; PubMed Central PMCID: PMC1151844. 7: Sakuno E, Wen Y, Hatabayashi H, Arai H, Aoki C, Yabe K, Nakajima H. Aspergillus parasiticus cyclase catalyzes two dehydration steps in aflatoxin biosynthesis. Appl Environ Microbiol. 2005 Jun;71(6):2999-3006. PubMed PMID: 15932995; PubMed Central PMCID: PMC1151850. 8: Yabe K, Nakajima H. Enzyme reactions and genes in aflatoxin biosynthesis. Appl Microbiol Biotechnol. 2004 Jun;64(6):745-55. Epub 2004 Mar 12. Review. PubMed PMID: 15022028. 9: Sakuno E, Yabe K, Nakajima H. Involvement of two cytosolic enzymes and a novel intermediate, 5'-oxoaverantin, in the pathway from 5'-hydroxyaverantin to averufin in aflatoxin biosynthesis. Appl Environ Microbiol. 2003 Nov;69(11):6418-26. PubMed PMID: 14602595; PubMed Central PMCID: PMC262255. 10: Maskey RP, Grün-Wollny I, Laatsch H. Isolation, structure elucidation and biological activity of 8-O-methylaverufin and 1,8-O-dimethylaverantin as new antifungal agents from Penicillium chrysogenum. J Antibiot (Tokyo). 2003 May;56(5):459-63. PubMed PMID: 12870811. 11: Yabe K, Chihaya N, Hamamatsu S, Sakuno E, Hamasaki T, Nakajima H, Bennett JW. Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis. Appl Environ Microbiol. 2003 Jan;69(1):66-73. PubMed PMID: 12513978; PubMed Central PMCID: PMC152417. 12: Hodges RL, Kelkar HS, Xuei X, Skatrud PL, Keller NP, Adams TH, Kaiser RE, Vinci VA, McGilvray D. Characterization of an echinocandin B-producing strain blocked for sterigmatocystin biosynthesis reveals a translocation in the stcW gene of the aflatoxin biosynthetic pathway. J Ind Microbiol Biotechnol. 2000 Dec;25(6):333-341. PubMed PMID: 11320421. 13: Chang PK, Yu J, Ehrlich KC, Boue SM, Montalbano BG, Bhatnagar D, Cleveland TE. adhA in Aspergillus parasiticus is involved in conversion of 5'-hydroxyaverantin to averufin. Appl Environ Microbiol. 2000 Nov;66(11):4715-9. PubMed PMID: 11055914; PubMed Central PMCID: PMC92370. 14: Yu J, Woloshuk CP, Bhatnagar D, Cleveland TE. Cloning and characterization of avfA and omtB genes involved in aflatoxin biosynthesis in three Aspergillus species. Gene. 2000 May 2;248(1-2):157-67. PubMed PMID: 10806361. 15: Keller NP, Watanabe CM, Kelkar HS, Adams TH, Townsend CA. Requirement of monooxygenase-mediated steps for sterigmatocystin biosynthesis by Aspergillus nidulans. Appl Environ Microbiol. 2000 Jan;66(1):359-62. PubMed PMID: 10618248; PubMed Central PMCID: PMC91830. 16: Hasan HA. Mode of action of pesticides on aflatoxin biosynthesis and oxidase system activity. Microbiol Res. 1999 May;154(1):95-102. PubMed PMID: 10356798. 17: Yu J, Chang PK, Cary JW, Bhatnagar D, Cleveland TE. avnA, a gene encoding a cytochrome P-450 monooxygenase, is involved in the conversion of averantin to averufin in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol. 1997 Apr;63(4):1349-56. PubMed PMID: 9097431; PubMed Central PMCID: PMC168428. 18: Prieto R, Yousibova GL, Woloshuk CP. Identification of aflatoxin biosynthesis genes by genetic complementation in an Aspergillus flavus mutant lacking the aflatoxin gene cluster. Appl Environ Microbiol. 1996 Oct;62(10):3567-71. PubMed PMID: 8967772; PubMed Central PMCID: PMC168161. 19: García ME, Herce MD, Blanco JL, Suárez G. A red pigment synthesized by an Aspergillus parasiticus mutant as a possible new intermediate in the aflatoxin biosynthetic pathway. J Appl Bacteriol. 1994 Nov;77(5):553-9. PubMed PMID: 8002480. 20: Yabe K, Matsuyama Y, Ando Y, Nakajima H, Hamasaki T. Stereochemistry during aflatoxin biosynthesis: conversion of norsolorinic acid to averufin. Appl Environ Microbiol. 1993 Aug;59(8):2486-92. PubMed PMID: 8368836; PubMed Central PMCID: PMC182310.