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MedKoo Cat#: 573341 | Name: Averantin
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Description:

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

Averufanin is an aflatoxin B1 precursor between averantin and averufin in the biosynthetic pathway

Chemical Structure

Averantin
Averantin
CAS#5803-62-3

Theoretical Analysis

MedKoo Cat#: 573341

Name: Averantin

CAS#: 5803-62-3

Chemical Formula: C20H20O7

Exact Mass: 372.1209

Molecular Weight: 372.37

Elemental Analysis: C, 64.51; H, 5.41; O, 30.08

Price and Availability

Size Price Availability Quantity
5mg USD 800.00 2 Weeks
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Related CAS #
No Data
Synonym
(-)-Averantin, Averantin
IUPAC/Chemical Name
(S)-1,3,6,8-tetrahydroxy-2-(1-hydroxyhexyl)anthracene-9,10-dione
InChi Key
WGPOPPKSQRZUTP-LBPRGKRZSA-N
InChi Code
InChI=1S/C20H20O7/c1-2-3-4-5-12(22)17-14(24)8-11-16(20(17)27)19(26)15-10(18(11)25)6-9(21)7-13(15)23/h6-8,12,21-24,27H,2-5H2,1H3/t12-/m0/s1
SMILES Code
O=C1C2=C(C=C(O)C=C2O)C(C3=CC(O)=C([C@@H](O)CCCCC)C(O)=C13)=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 372.37 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
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PMID: 3103529; PMCID: PMC203593. 4: 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. doi: 10.1128/aem.63.4.1349-1356.1997. PMID: 9097431; PMCID: PMC168428. 5: 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. PMID: 18615624. 6: Du W, Obrian GR, Payne GA. Function and regulation of aflJ in the accumulation of aflatoxin early pathway intermediate in Aspergillus flavus. Food Addit Contam. 2007 Oct;24(10):1043-50. doi: 10.1080/02652030701513826. PMID: 17886176. 7: Birkinshaw JH, Roberts JC, Roffey P. Studies in mycological chemistry. XIX. "Product B" (averantin) [1,3,6,8-tetrahydroxy-2-(1-hydroxyhexyl)anthraquinone], a pigment from Aspergillus versicolor (Vuillemin) Tiraboschi. J Chem Soc Perkin 1. 1966;9:855-7. doi: 10.1039/j39660000855. PMID: 5948685. 8: Li H, Wei J, Pan SY, Gao JM, Tian JM. Antifungal, phytotoxic and toxic metabolites produced by Penicillium purpurogenum. Nat Prod Res. 2014;28(24):2358-61. doi: 10.1080/14786419.2014.940586. Epub 2014 Aug 7. PMID: 25103412. 9: Tatsuda D, Momose I, Someno T, Sawa R, Kubota Y, Iijima M, Kunisada T, Watanabe T, Shibasaki M, Nomoto A. Quinofuracins A-E, produced by the fungus Staphylotrichum boninense PF1444, show p53-dependent growth suppression. J Nat Prod. 2015 Feb 27;78(2):188-95. doi: 10.1021/np500581m. Epub 2015 Jan 22. PMID: 25611347. 10: 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. PMID: 25022791. 11: Huang H, Wang F, Luo M, Chen Y, Song Y, Zhang W, Zhang S, Ju J. Halogenated anthraquinones from the marine-derived fungus Aspergillus sp. SCSIO F063. J Nat Prod. 2012 Jul 27;75(7):1346-52. doi: 10.1021/np3002699. Epub 2012 Jun 15. PMID: 22703109. 12: Cleveland TE, Bhatnagar D, Foell CJ, McCormick SP. Conversion of a new metabolite to aflatoxin B2 by Aspergillus parasiticus. Appl Environ Microbiol. 1987 Dec;53(12):2804-7. doi: 10.1128/aem.53.12.2804-2807.1987. PMID: 3435144; PMCID: PMC204202. 13: Lai P, Wang L, Deng C, Xu Y, Ma XY, Cheng CR, Huang SX. Asperidulins A and B, two new prenylxanthone derivatives from an apple-derived fungus Aspergillus nidulans KIB-HACM-01. Nat Prod Res. 2023 Mar 6:1-7. doi: 10.1080/14786419.2023.2185889. Epub ahead of print. PMID: 36876408. 14: Liang X, Huang ZH, Ma X, Zheng ZH, Zhang XX, Lu XH, Qi SH. Mycotoxins as inhibitors of protein tyrosine phosphatases from the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Bioorg Chem. 2021 Feb;107:104571. doi: 10.1016/j.bioorg.2020.104571. Epub 2020 Dec 19. PMID: 33373758. 15: Anh CV, Kang JS, Choi BK, Lee HS, Heo CS, Shin HJ. Polyketides and Meroterpenes from the Marine-Derived Fungi Aspergillus unguis 158SC-067 and A. flocculosus 01NT-1.1.5 and Their Cytotoxic and Antioxidant Activities. Mar Drugs. 2021 Jul 26;19(8):415. doi: 10.3390/md19080415. PMID: 34436253; PMCID: PMC8402063. 16: 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. doi: 10.1016/j.bioorg.2005.09.002. Epub 2005 Nov 2. PMID: 16260026. 17: Chang PK, Cary JW, Yu J, Bhatnagar D, Cleveland TE. The Aspergillus parasiticus polyketide synthase gene pksA, a homolog of Aspergillus nidulans wA, is required for aflatoxin B1 biosynthesis. Mol Gen Genet. 1995 Aug 21;248(3):270-7. doi: 10.1007/BF02191593. PMID: 7565588. 18: Ehrlich K. Effect on aflatoxin production of competition between wild-type and mutant strains of Aspergillus parasiticus. Mycopathologia. 1987 Feb;97(2):93-6. doi: 10.1007/BF00436844. PMID: 3574436. 19: 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. doi: 10.7164/antibiotics.56.459. PMID: 12870811. 20: 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. doi: 10.1128/AEM.71.6.2999-3006.2005. 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