MedKoo Cat#: 592859 | Name: Amphidinolide D

Description:

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

Amphidinolide D is a powerful activator of actomyosin ATPase enhances skeletal muscle contraction.

Chemical Structure

Amphidinolide D
Amphidinolide D
CAS#110786-78-2

Theoretical Analysis

MedKoo Cat#: 592859

Name: Amphidinolide D

CAS#: 110786-78-2

Chemical Formula: C32H50O8

Exact Mass: 562.3506

Molecular Weight: 562.74

Elemental Analysis: C, 68.30; H, 8.96; O, 22.74

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
Amphidinolide D
IUPAC/Chemical Name
(1S,2E,6E,10S,12R,13S,14R,17R,19S,20E,24R,26S)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-9,27-dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione
InChi Key
PYXZGBVSQBXPDQ-VQFFCZPRSA-N
InChi Code
InChI=1S/C32H50O8/c1-19-13-20(2)15-28-27(40-28)12-10-8-9-11-21(3)31(37)39-24(6)16-22(4)29(35)30(36)26(34)17-25(33)18-32(7,38)23(5)14-19/h10-12,14,20,22,24-25,27-30,33,35-36,38H,1,8-9,13,15-18H2,2-7H3/b12-10+,21-11+,23-14+/t20-,22-,24+,25+,27+,28+,29+,30+,32+/m1/s1
SMILES Code
C=1[C@@H]2O[C@H]2C[C@@H](CC(C=C([C@@](C[C@H](CC([C@@H]([C@H]([C@@H](C[C@@H](OC(C(=CCCC1)C)=O)C)C)O)O)=O)O)(C)O)C)=C)C
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 562.74 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: Matsunaga K, Nakatani K, Ishibashi M, Kobayashi J, Ohizumi Y. Amphidinolide B, a powerful activator of actomyosin ATPase enhances skeletal muscle contraction. Biochim Biophys Acta. 1999 Mar 14;1427(1):24-32. PubMed PMID: 10082984. 2: Lu L, Zhang W, Carter RG. Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2. J Am Chem Soc. 2008 Jun 11;130(23):7253-5. doi: 10.1021/ja803012n. Epub 2008 May 20. Erratum in: J Am Chem Soc. 2008 Sep 3;130(35):11834. PubMed PMID: 18489095; PubMed Central PMCID: PMC2435505. 3: Sidera M, Costa AM, Vilarrasa J. Iododesilylation of TIPS-, TBDPS-, and TBS-substituted alkenes in connection with the synthesis of amphidinolides B/D. Org Lett. 2011 Sep 16;13(18):4934-7. doi: 10.1021/ol2020187. Epub 2011 Aug 25. PubMed PMID: 21866884. 4: Tsuda M, Kubota T, Sakuma Y, Kobayashi J. Biosynthetic study of amphidinolide B. Chem Pharm Bull (Tokyo). 2001 Oct;49(10):1366-7. PubMed PMID: 11605674. 5: Gopalarathnam A, Nelson SG. Amphidinolide B: asymmetric synthesis of a C7-C20 synthon. Org Lett. 2006 Jan 5;8(1):7-10. PubMed PMID: 16381554. 6: Kobayashi J, Ishibashi M, Nakamura H, Ohizumi Y, Yamasu T, Hirata Y, Sasaki T, Ohta T, Nozoe S. Cytotoxic macrolides from a cultured marine dinoflagellate of the genus Amphidinium. J Nat Prod. 1989 Sep-Oct;52(5):1036-41. PubMed PMID: 2607346. 7: Hara A, Morimoto R, Iwasaki Y, Saitoh T, Ishikawa Y, Nishiyama S. Total syntheses of amphidinolides B, G, and H. Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9877-80. doi: 10.1002/anie.201204992. Epub 2012 Aug 24. PubMed PMID: 22927025. 8: Zhang W, Carter RG, Yokochi AF. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions. J Org Chem. 2004 Apr 2;69(7):2569-72. PubMed PMID: 15049660; PubMed Central PMCID: PMC2430272.