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MedKoo Cat#: 412788 | Name: Chaetochromin

Description:

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

Chaetochromin also known as 4548-G05 and NSC 345647, is an orally active, small-molecule, selective agonist of the insulin receptor. It has potent and long-lasting antidiabetic activity in vivo in mice.

Chemical Structure

Chaetochromin
Chaetochromin
CAS#75514-37-3

Theoretical Analysis

MedKoo Cat#: 412788

Name: Chaetochromin

CAS#: 75514-37-3

Chemical Formula: C30H26O10

Exact Mass: 546.1526

Molecular Weight: 546.53

Elemental Analysis: C, 65.93; H, 4.80; O, 29.27

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 #
No Data
Synonym
Chaetochromin; Chaetochromin A; 4548-G05; NSC345647; NSC-345647; NSC 345647
IUPAC/Chemical Name
(2R,2'R,3R,3'R)-5,5',6,6',8,8'-hexahydroxy-2,2',3,3'-tetramethyl-2,2',3,3'-tetrahydro-4H,4'H-[9,9'-bibenzo[g]chromene]-4,4'-dione
InChi Key
RHNVLFNWDGWACV-DDHJBXDOSA-N
InChi Code
InChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3/t9-,10-,11-,12-/m1/s1
SMILES Code
C[C@H]1Oc(c2)c(C([C@@H]1C)=O)c(O)c3c2c(c(c(O)cc4O)c5c4c(O)c(C([C@@H]([C@H](O6)C)C)=O)c6c5)c(O)cc3O
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
>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
More Info
Solvent mg/mL mM comments
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 546.53 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: Mori S, Kawai K, Nozawa Y, Koyama K, Natori S. The impairing effects of chaetochromin D on mitochondrial respiration and structure. Mycotoxin Res. 1993 Sep;9(2):85-93. doi: 10.1007/BF03192239. PMID: 23606174. 2: Koyama K, Natori S. Biosynthesis of chaetochromin A, a bis(naphtho-gamma- pyrone), in Chaetomium spp. Chem Pharm Bull (Tokyo). 1989 Aug;37(8):2022-5. doi: 10.1248/cpb.37.2022. PMID: 2598307. 3: Omer A, Singh P. An integrated approach of network-based systems biology, molecular docking, and molecular dynamics approach to unravel the role of existing antiviral molecules against AIDS-associated cancer. J Biomol Struct Dyn. 2017 May;35(7):1547-1558. doi: 10.1080/07391102.2016.1188417. Epub 2016 Aug 2. PMID: 27484103. 4: Cardellina JH 2nd, Roxas-Duncan VI, Montgomery V, Eccard V, Campbell Y, Hu X, Khavrutskii I, Tawa GJ, Wallqvist A, Gloer JB, Phatak NL, Höller U, Soman AG, Joshi BK, Hein SM, Wicklow DT, Smith LA. Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A. ACS Med Chem Lett. 2012 Apr 2;3(5):387-91. doi: 10.1021/ml200312s. PMID: 24900483; PMCID: PMC4025784. 5: Koyama K, Ominato K, Natori S, Tashiro T, Tsuruo T. Cytotoxicity and antitumor activities of fungal bis(naphtho-gamma-pyrone) derivatives. J Pharmacobiodyn. 1988 Sep;11(9):630-5. doi: 10.1248/bpb1978.11.630. PMID: 2464052. 6: Ishii R, Horie M, Koyama K, Ishikawa Y, Kitanaka S. Inhibitory effects of fungal bis(naphtho-gamma-pyrone) derivatives on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-gamma. Biol Pharm Bull. 2005 May;28(5):786-90. doi: 10.1248/bpb.28.786. PMID: 15863879. 7: Sekita S, Yoshihira K, Natori S, Udagawa S, Muroi T, Sugiyama Y, Kurata H, Umeda M. Mycotoxin production by Chaetomium spp. and related fungi. Can J Microbiol. 1981 Aug;27(8):766-72. doi: 10.1139/m81-119. PMID: 7296410. 8: Singh SB, Zink DL, Bills GF, Teran A, Silverman KC, Lingham RB, Felock P, Hazuda DJ. Four novel bis-(naphtho-gamma-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase. Bioorg Med Chem Lett. 2003 Feb 24;13(4):713-7. doi: 10.1016/s0960-894x(02)01057-0. PMID: 12639565. 9: Ito Y, Ohtsubo K. Teratogenicity of oral chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp., to mice embryo. Bull Environ Contam Toxicol. 1987 Aug;39(2):299-303. doi: 10.1007/BF01689421. PMID: 3663985. 10: Qiang G, Xue S, Yang JJ, Du G, Pang X, Li X, Goswami D, Griffin PR, Ortlund EA, Chan CB, Ye K. Identification of a small molecular insulin receptor agonist with potent antidiabetes activity. Diabetes. 2014 Apr;63(4):1394-409. doi: 10.2337/db13-0334. PMID: 24651808; PMCID: PMC3964510.