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MedKoo Cat#: 463025 | Name: Amphidinolide A

Description:

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

Amphidinolide A is a novel 20-membered macrolide. It has been shown to exhibit antineoplastic activity.

Chemical Structure

Amphidinolide A
Amphidinolide A
CAS#106463-75-6

Theoretical Analysis

MedKoo Cat#: 463025

Name: Amphidinolide A

CAS#: 106463-75-6

Chemical Formula: C31H46O7

Exact Mass: 530.3244

Molecular Weight: 530.70

Elemental Analysis: C, 70.16; H, 8.74; O, 21.10

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
Amphidinolide A;
IUPAC/Chemical Name
(3Z,5Z,9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-8,11,17-trimethylene-20-((2R,3S)-3-((S)-pentan-2-yl)oxiran-2-yl)oxacycloicosa-3,5,14-trien-2-one
InChi Key
NFOKXEYWZUZJRF-FMZZXDJESA-N
InChi Code
InChI=1S/C31H46O7/c1-8-11-21(5)29-31(38-29)30-22(6)16-18(2)13-10-15-24(32)27(35)23(7)28(36)26(34)20(4)14-9-12-19(3)17-25(33)37-30/h9-10,12,15,17,21-22,24,26-32,34-36H,2,4,7-8,11,13-14,16H2,1,3,5-6H3/b12-9-,15-10-,19-17-/t21-,22-,24-,26-,27-,28-,29-,30+,31+/m0/s1
SMILES Code
CCC[C@@H]([C@@H]1O[C@H]1[C@@H]2OC(/C=C(\C=C/CC([C@@H]([C@H](C([C@@H]([C@H](/C=C\CC(C[C@@H]2C)=C)O)O)=C)O)O)=C)C)=O)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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 530.70 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: Morris JC, Nicholas GM, Phillips AJ. Marine natural products: synthetic aspects. Nat Prod Rep. 2007 Feb;24(1):87-108. doi: 10.1039/b602832m. Epub 2007 Jan 4. PMID: 17268608. 2: Nicholas GM, Phillips AJ. Marine natural products: synthetic aspects. Nat Prod Rep. 2006 Feb;23(1):79-99. doi: 10.1039/b501014b. Epub 2006 Jan 5. PMID: 16453032. 3: Trost BM, Harrington PE, Chisholm JD, Wrobleski ST. Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis. J Am Chem Soc. 2005 Oct 5;127(39):13598-610. doi: 10.1021/ja053365y. PMID: 16190725. 4: Trost BM, Wrobleski ST, Chisholm JD, Harrington PE, Jung M. Total synthesis of (+)-amphidinolide A. Assembly of the fragments. J Am Chem Soc. 2005 Oct 5;127(39):13589-97. doi: 10.1021/ja0533646. PMID: 16190724. 5: Trost BM, Harrington PE. Structure elucidation of (+)-amphidinolide a by total synthesis and NMR chemical shift analysis. J Am Chem Soc. 2004 Apr 28;126(16):5028-9. doi: 10.1021/ja049292k. PMID: 15099060. 6: Lam HW, Pattenden G. Total synthesis of the presumed amphidinolide A. Angew Chem Int Ed Engl. 2002 Feb 1;41(3):508-11. doi: 10.1002/1521-3773(20020201)41:3<508::aid-anie508>3.0.co;2-7. PMID: 12491395. 7: Trost BM, Chisholm JD, Wrobleski ST, Jung M. Ruthenium-catalyzed alkene- alkyne coupling: synthesis of the proposed structure of amphidinolide A. J Am Chem Soc. 2002 Oct 23;124(42):12420-1. doi: 10.1021/ja027883+. PMID: 12381177. 8: Maleczka RE Jr, Terrell LR, Geng F, Ward JS 3rd. Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis. Org Lett. 2002 Aug 22;4(17):2841-4. doi: 10.1021/ol0262284. PMID: 12182569. 9. https://www.sciencedirect.com/science/article/abs/pii/S0040403900853186.