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MedKoo Cat#: 412790 | Name: Chaetochromin D

Description:

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

Chaetochromin D also known as 4548-G05, is an orally active, small-molecule, selective agonist of the insulin receptor.

Chemical Structure

Chaetochromin D
Chaetochromin D
CAS#108906-67-8

Theoretical Analysis

MedKoo Cat#: 412790

Name: Chaetochromin D

CAS#: 108906-67-8

Chemical Formula: C30H24O10

Exact Mass: 544.1369

Molecular Weight: 544.51

Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

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
Chaetochromin D; UNII-P5G8T58C00
IUPAC/Chemical Name
(2R,3R)-5,5',6,6',8,8'-hexahydroxy-2,2',3,3'-tetramethyl-2,3-dihydro-4H,4'H-[9,9'-bibenzo[g]chromene]-4,4'-dione
InChi Key
OXYDHUNPMSPUCC-MWLCHTKSSA-N
InChi Code
InChI=1S/C30H24O10/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/h5-9,11,31-34,37-38H,1-4H3/t9-,11-/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(C)=C(O6)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

Preparing Stock Solutions

The following data is based on the product molecular weight 544.51 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: 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. 10: Paranagama PA, Wijeratne EM, Gunatilaka AA. Uncovering biosynthetic potential of plant-associated fungi: effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii. J Nat Prod. 2007 Dec;70(12):1939-45. doi: 10.1021/np070504b. Epub 2007 Dec 6. PMID: 18052326.