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MedKoo Cat#: 461691 | Name: Secalonic acid D

Description:

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

Secalonic acid D is a metabolite of marine-derived mangrove endophytic fungus that exhibits potent antiangiogenic antitumor activity.

Chemical Structure

Secalonic acid D
Secalonic acid D
CAS#35287-69-5

Theoretical Analysis

MedKoo Cat#: 461691

Name: Secalonic acid D

CAS#: 35287-69-5

Chemical Formula: C32H30O14

Exact Mass: 638.1636

Molecular Weight: 638.57

Elemental Analysis: C, 60.19; H, 4.74; O, 35.08

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
Secalonic acid D; Secalonic acid D mycotoxin; Ergochrome EE; NSC 159631; NSC159631; NSC-159631; NSC268922; NSC-268922; NSC 268922;
IUPAC/Chemical Name
dimethyl (5R,5'R,6S,6'S,10aR,10'aR)-1,1',5,5',8,8'-hexahydroxy-6,6'-dimethyl-9,9'-dioxo-5,5',6,6',7,7',9,9'-octahydro-10aH,10'aH-[2,2'-bixanthene]-10a,10'a-dicarboxylate
InChi Key
DRYDKQOPVBDZMQ-OCHURCMPSA-N
InChi Code
InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,33-36,39-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m0/s1
SMILES Code
O=C([C@@]1([C@H](O)[C@@H](C)CC(O)=C12)OC3=C(C(O)=C(C4=C(O)C(C5=O)=C(O[C@@]6(C(OC)=O)[C@H](O)[C@@H](C)CC(O)=C65)C=C4)C=C3)C2=O)OC
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 638.57 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: Guru SK, Pathania AS, Kumar S, Ramesh D, Kumar M, Rana S, Kumar A, Malik F, Sharma PR, Chandan BK, Jaglan S, Sharma JP, Shah BA, Tasduq SA, Lattoo SK, Faruk A, Saxena AK, Vishwakarma RA, Bhushan S. Secalonic Acid-D Represses HIF1α/VEGF-Mediated Angiogenesis by Regulating the Akt/mTOR/p70S6K Signaling Cascade. Cancer Res. 2015 Jul 15;75(14):2886-96. doi: 10.1158/0008-5472.CAN-14-2312. Epub 2015 May 14. PubMed PMID: 25977334. 2: Hu YP, Tao LY, Wang F, Zhang JY, Liang YJ, Fu LW. Secalonic acid D reduced the percentage of side populations by down-regulating the expression of ABCG2. Biochem Pharmacol. 2013 Jun 1;85(11):1619-25. doi: 10.1016/j.bcp.2013.04.003. Epub 2013 Apr 10. PubMed PMID: 23583455. 3: Wang BH, Polya GM. The fungal teratogen secalonic acid D is an inhibitor of protein kinase C and of cyclic AMP-dependent protein kinase. Planta Med. 1996 Apr;62(2):111-4. PubMed PMID: 8657739. 4: Hong R. Secalonic acid D as a novel DNA topoisomerase I inhibitor from marine lichen-derived fungus Gliocladium sp. T31. Pharm Biol. 2011 Aug;49(8):796-9. doi: 10.3109/13880209.2010.548817. Epub 2011 Apr 15. PubMed PMID: 21495809. 5: Zhang JY, Tao LY, Liang YJ, Yan YY, Dai CL, Xia XK, She ZG, Lin YC, Fu LW. Secalonic acid D induced leukemia cell apoptosis and cell cycle arrest of G(1) with involvement of GSK-3beta/beta-catenin/c-Myc pathway. Cell Cycle. 2009 Aug;8(15):2444-50. Epub 2009 Aug 3. PubMed PMID: 19571678. 6: Reddy CS, Reddy RV, Chan PK, Hayes AW. Mutagenicity of secalonic acid D in mice. J Environ Pathol Toxicol. 1980 Nov;4(5-6):31-7. PubMed PMID: 7217855. 7: Reddy CS, Reddy RV, Hayes AW, Ciegler A. Teratogenicity of secalonic acid D in mice. J Toxicol Environ Health. 1981 Mar-Apr;7(3-4):445-55. PubMed PMID: 7288897. 8: Dhulipala VC, Maddali KK, Ray BK, Welshons WV, Reddy CS. Role of p21 and cyclin E in normal and secalonic acid D-inhibited proliferation of human embryonic palatal mesenchymal cells. Hum Exp Toxicol. 2011 Sep;30(9):1222-32. doi: 10.1177/0960327110387238. Epub 2010 Oct 18. PubMed PMID: 20956459. 9: Liao G, Zhou J, Wang H, Mao Z, Xiao W, Wang H, She Z, Zhu Y. The cell toxicity effect of secalonic acid D on GH3 cells and the related mechanisms. Oncol Rep. 2010 Feb;23(2):387-95. PubMed PMID: 20043099. 10: Mayura K, Hayes AW, Berndt WO. Teratogenicity of secalonic acid D in rats. Toxicology. 1982;25(4):311-22. PubMed PMID: 7157407. 11: Kawai K, Nakamaru T, Maebayashi Y, Nozawa Y, Yamazaki M. Inhibition by secalonic acid D of oxidative phosphorylation and Ca2+-induced swelling in mitochondria isolated from rat livers. Appl Environ Microbiol. 1983 Oct;46(4):793-6. PubMed PMID: 6227285; PubMed Central PMCID: PMC239469. 12: Qin T, Porco JA Jr. Total syntheses of secalonic acids A and D. Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3107-10. doi: 10.1002/anie.201311260. Epub 2014 Feb 12. PubMed PMID: 24519991; PubMed Central PMCID: PMC4098722. 13: Dhulipala VC, Maddali KK, Welshons WV, Reddy CS. Secalonic acid D blocks embryonic palatal mesenchymal cell-cycle by altering the activity of CDK2 and the expression of p21 and cyclin E. Birth Defects Res B Dev Reprod Toxicol. 2005 Jun;74(3):233-42. PubMed PMID: 15880679. 14: Reddy CS, Hayes AW, Williams WL, Ciegler A. Toxicity of Secalonic acid D. J Toxicol Environ Health. 1979 Nov;5(6):1159-69. PubMed PMID: 529343. 15: Reddy RV, Eldeib MM, Reddy CS. Inhibition of adenylate cyclase in perfusion mouse palate by secalonic acid D. J Toxicol Environ Health. 1994 Feb;41(2):175-85. PubMed PMID: 8301697. 16: Bolon B, St Omer VE. Behavioral and developmental effects in suckling mice following maternal exposure to the mycotoxin secalonic acid D. Pharmacol Biochem Behav. 1989 Oct;34(2):229-36. PubMed PMID: 2622978. 17: Ganapathy D, Reiner JR, Löffler LE, Ma L, Gnanaprakasam B, Niepötter B, Koehne I, Tietze LF. Enantioselective Total Synthesis of Secalonic Acid E. Chemistry. 2015 Nov 16;21(47):16807-10. doi: 10.1002/chem.201503593. Epub 2015 Oct 8. PubMed PMID: 26447631. 18: Dhulipala VC, Welshons WV, Reddy CS. Inhibition of human embryonic palatal mesenchymal cell cycle by secalonic acid D: a probable mechanism of its cleft palate induction. Orthod Craniofac Res. 2004 Nov;7(4):227-36. PubMed PMID: 15562586. 19: Zhai A, Zhang Y, Zhu X, Liang J, Wang X, Lin Y, Chen R. Secalonic acid A reduced colchicine cytotoxicity through suppression of JNK, p38 MAPKs and calcium influx. Neurochem Int. 2011 Jan;58(1):85-91. doi: 10.1016/j.neuint.2010.10.016. Epub 2010 Nov 10. PubMed PMID: 21073911. 20: Zhai A, Zhu X, Wang X, Chen R, Wang H. Secalonic acid A protects dopaminergic neurons from 1-methyl-4-phenylpyridinium (MPP⁺)-induced cell death via the mitochondrial apoptotic pathway. Eur J Pharmacol. 2013 Aug 5;713(1-3):58-67. doi: 10.1016/j.ejphar.2013.04.029. Epub 2013 May 9. PubMed PMID: 23665112.