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MedKoo Cat#: 574635 | Name: Cochlioquinone A
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Description:

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

Cochlioquinone A is an inhibitor of diacylglycerol kinase (DGK) and diacylglycerol acyltransferase (DGAT). It has been shown to reduce the concentration of phosphatidic acid in T cell lymphoma and has also been shown to compete with macrophage inflammatory protein-1α for binding to human CCR5 chemokine receptors.

Chemical Structure

Cochlioquinone A
Cochlioquinone A
CAS#32450-25-2

Theoretical Analysis

MedKoo Cat#: 574635

Name: Cochlioquinone A

CAS#: 32450-25-2

Chemical Formula: C30H44O8

Exact Mass: 532.3036

Molecular Weight: 532.67

Elemental Analysis: C, 67.65; H, 8.33; O, 24.03

Price and Availability

Size Price Availability Quantity
500µg USD 500.00 2 Weeks
2.5mg USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Cochlioquinone A; Coclioquinone A; CochlioquinoneA
IUPAC/Chemical Name
(2S,3R,4S)-2-((3R,4aR,6aR,12S,12aS,12bR)-12-hydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-8,11-dioxo-1,2,3,4a,5,6,6a,8,11,12,12a,12b-dodecahydropyrano[3,2-a]xanthen-9-yl)-4-methylhexan-3-yl acetate
InChi Key
UWSYUCZPPVXEKW-MHUJPXPPSA-N
InChi Code
InChI=1S/C30H44O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,34-35H,9-13H2,1-8H3/t15-,16-,20+,21+,24+,25+,27+,29-,30+/m0/s1
SMILES Code
C[C@]12[C@@](O[C@@H](C(C)(O)C)CC2)([H])CC[C@@]([C@]1([H])[C@@H]3O)(C)OC4=C3C(C=C([C@H](C)[C@H](OC(C)=O)[C@@H](C)CC)C4=O)=O
Appearance
A yellow lyophilisate
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 532.67 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: Zhu P, Bu H, Tan S, Liu J, Yuan B, Dong G, Wang M, Jiang Y, Zhu H, Li H, Li Z, Jiang J, Wu M, Li R. A Novel Cochlioquinone Derivative, CoB1, Regulates Autophagy in Pseudomonas aeruginosa Infection through the PAK1/Akt1/mTOR Signaling Pathway. J Immunol. 2020 Sep 1;205(5):1293-1305. doi: 10.4049/jimmunol.1901346. Epub 2020 Aug 3. PMID: 32747503. 2: Machida T, Higashi K, Ogawara H. Cochlioquinone A, an inhibitor of diacylglycerol kinase. J Antibiot (Tokyo). 1995 Oct;48(10):1076-80. doi: 10.7164/antibiotics.48.1076. PMID: 7490210. 3: Fujioka T, Yao K, Hamano K, Hosoya T, Kagasaki T, Furukawa Y, Haruyama H, Sato S, Koga T, Tsujita Y. Epi-cochlioquinone A, a novel acyl-CoA : cholesterol acyltransferase inhibitor produced by Stachybotrys bisbyi. J Antibiot (Tokyo). 1996 May;49(5):409-13. doi: 10.7164/antibiotics.49.409. PMID: 8682715. 4: Schaeffer JM, Frazier EG, Bergstrom AR, Williamson JM, Liesch JM, Goetz MA. Cochlioquinone A, a nematocidal agent which competes for specific [3H]ivermectin binding sites. J Antibiot (Tokyo). 1990 Sep;43(9):1179-82. doi: 10.7164/antibiotics.43.1179. PMID: 2211380. 5: Jung HJ, Burm Lee H, Lim CH, Kim CJ, Kwon HJ. Cochlioquinone A1, a new anti- angiogenic agent from Bipolaris zeicola. Bioorg Med Chem. 2003 Nov 3;11(22):4743-7. doi: 10.1016/s0968-0896(03)00523-6. PMID: 14556789. 6: Qi QY, Huang L, He LW, Han JJ, Chen Q, Cai L, Liu HW. Cochlioquinone derivatives with apoptosis-inducing effects on HCT116 colon cancer cells from the phytopathogenic fungus Bipolaris luttrellii L439. Chem Biodivers. 2014 Dec;11(12):1892-9. doi: 10.1002/cbdv.201400106. PMID: 25491333. 7: Feng L, Wang XJ, Li L, Zhang AX, Shang RR, Tan NH, Wang Z. Identification of meroterpenoids from Bipolaris victoriae S27 and their potential activity against tumor metastasis and inhibition of the NF-κB signaling pathway. Phytochemistry. 2022 Aug;200:113180. doi: 10.1016/j.phytochem.2022.113180. Epub 2022 Apr 12. PMID: 35427653. 8: Han J, Zhang J, Song Z, Zhu G, Liu M, Dai H, Hsiang T, Liu X, Zhang L, Quinn RJ, Feng Y. Genome-based mining of new antimicrobial meroterpenoids from the phytopathogenic fungus Bipolaris sorokiniana strain 11134. Appl Microbiol Biotechnol. 2020 May;104(9):3835-3846. doi: 10.1007/s00253-020-10522-1. Epub 2020 Mar 26. PMID: 32215711. 9: do Nascimento AM, Soares MG, da Silva Torchelsen FK, de Araujo JA, Lage PS, Duarte MC, Andrade PH, Ribeiro TG, Coelho EA, do Nascimento AM. Antileishmanial activity of compounds produced by endophytic fungi derived from medicinal plant Vernonia polyanthes and their potential as source of bioactive substances. World J Microbiol Biotechnol. 2015 Nov;31(11):1793-800. doi: 10.1007/s11274-015-1932-0. Epub 2015 Aug 29. PMID: 26318306. 10: Fujioka T. [Inhibitory action of natural compounds of microbial origin on cholesterol metabolism]. Nihon Yakurigaku Zasshi. 1997 Oct;110 Suppl 1:75P-80P. Japanese. doi: 10.1254/fpj.110.supplement_75. PMID: 9503410. 11: Campos FF, Rosa LH, Cota BB, Caligiorne RB, Rabello AL, Alves TM, Rosa CA, Zani CL. Leishmanicidal metabolites from Cochliobolus sp., an endophytic fungus isolated from Piptadenia adiantoides (Fabaceae). PLoS Negl Trop Dis. 2008;2(12):e348. doi: 10.1371/journal.pntd.0000348. Epub 2008 Dec 16. Erratum in: PLoS Negl Trop Dis. 2009;3(1). doi: 10.1371/annotation/49748d99-fe4d-4c28-b77a-306d0cf7062e. PMID: 19079599; PMCID: PMC2593781. 12: Bicalho B, Gonçalves RA, Zibordi AP, Manfio GP, Marsaioli AJ. Antimicrobial compounds of fungi vectored by Clusia spp. (Clusiaceae) pollinating bees. Z Naturforsch C J Biosci. 2003 Sep-Oct;58(9-10):746-51. doi: 10.1515/znc-2003-9-1027. PMID: 14577643. 13: Lee HB, Lim CH, Kwon HJ, Kim YK, Lee HS, Kim CJ. Inhibitory activity of diacylglycerol acyltransferase by cochlioquinones A and A1. J Antibiot (Tokyo). 2003 Nov;56(11):967-9. doi: 10.7164/antibiotics.56.967. PMID: 14763563. 14: Ogawara H, Higashi K, Machida T, Takashima J, Chiba N, Mikawa T. Inhibitors of diacylglycerol kinase from Drechslera sacchari. J Antibiot (Tokyo). 1994 Apr;47(4):499-501. doi: 10.7164/antibiotics.47.499. PMID: 8195052. 15: Yoganathan K, Yang LK, Rossant C, Huang Y, Ng S, Butler MS, Buss AD. Cochlioquinones and epi-cochlioquinones: antagonists of the human chemokine receptor CCR5 from Bipolaris brizae and Stachybotrys chartarum. J Antibiot (Tokyo). 2004 Jan;57(1):59-63. doi: 10.7164/antibiotics.57.59. PMID: 15032487.