MedKoo Cat#: 413299 | Name: Costatolide

Description:

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

Costatolide is isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. It has a role as a HIV-1 reverse transcriptase inhibitor and a plant metabolite. It is a delta-lactone, a cyclic ether, a secondary alcohol and an organic heterotetracyclic compound.

Chemical Structure

Costatolide
Costatolide
CAS#909-14-8

Theoretical Analysis

MedKoo Cat#: 413299

Name: Costatolide

CAS#: 909-14-8

Chemical Formula: C22H26O5

Exact Mass: 370.1780

Molecular Weight: 370.45

Elemental Analysis: C, 71.33; H, 7.07; O, 21.59

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
Costatolide; NSC661122; NSC-661122; NSC 661122
IUPAC/Chemical Name
2H,6H,10H-Benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,(10S,11R,12S)-
InChi Key
NIDRYBLTWYFCFV-PZROIBLQSA-N
InChi Code
InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18-/m0/s1
SMILES Code
O=C1C=C(CCC)C2=C3C(C=CC(C)(C)O3)=C4C([C@@H](O)[C@@H](C)[C@H](C)O4)=C2O1
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 370.45 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: Buckheit RW Jr, White EL, Fliakas-Boltz V, Russell J, Stup TL, Kinjerski TL, Osterling MC, Weigand A, Bader JP. Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob Agents Chemother. 1999 Aug;43(8):1827-34. doi: 10.1128/AAC.43.8.1827. PMID: 10428899; PMCID: PMC89377. 2: Spino C, Dodier M, Sotheeswaran S. Anti-HIV coumarins from Calophyllum seed oil. Bioorg Med Chem Lett. 1998 Dec 15;8(24):3475-8. doi: 10.1016/s0960-894x(98)00628-3. PMID: 9934455. 3: Nahar L, Talukdar AD, Nath D, Nath S, Mehan A, Ismail FMD, Sarker SD. Naturally Occurring Calanolides: Occurrence, Biosynthesis, and Pharmacological Properties Including Therapeutic Potential. Molecules. 2020 Oct 28;25(21):4983. doi: 10.3390/molecules25214983. PMID: 33126458; PMCID: PMC7663239. 4: Buckheit RW Jr, Russell JD, Pallansch LA, Driscoll JS. Anti-human immunodeficiency virus type 1 (HIV-1) activity of 2'-fluoro-2',3'-dideoxyarabinosyladenine (F-ddA) used in combination with other mechanistically diverse inhibitors of HIV-1 replication. Antivir Chem Chemother. 1999 May;10(3):115-9. doi: 10.1177/095632029901000302. PMID: 10431610. 5: Buckheit RW Jr, Russell JD, Xu ZQ, Flavin M. Anti-HIV-1 activity of calanolides used in combination with other mechanistically diverse inhibitors of HIV-1 replication. Antivir Chem Chemother. 2000 Sep;11(5):321-7. doi: 10.1177/095632020001100502. PMID: 11142630. 6: Buckheit RW Jr, Kinjerski TL, Fliakas-Boltz V, Russell JD, Stup TL, Pallansch LA, Brouwer WG, Dao DC, Harrison WA, Schultz RJ, et al. Structure-activity and cross-resistance evaluations of a series of human immunodeficiency virus type-1-specific compounds related to oxathiin carboxanilide. Antimicrob Agents Chemother. 1995 Dec;39(12):2718-27. doi: 10.1128/aac.39.12.2718. PMID: 8593008; PMCID: PMC163018. 7: Buckheit RW Jr, Snow MJ, Fliakas-Boltz V, Kinjerski TL, Russell JD, Pallansch LA, Brouwer WG, Yang SS. Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. Antimicrob Agents Chemother. 1997 Apr;41(4):831-7. doi: 10.1128/AAC.41.4.831. PMID: 9087499; PMCID: PMC163804. 8: Usach I, Melis V, Peris JE. Non-nucleoside reverse transcriptase inhibitors: a review on pharmacokinetics, pharmacodynamics, safety and tolerability. J Int AIDS Soc. 2013 Sep 4;16(1):1-14. doi: 10.7448/IAS.16.1.18567. PMID: 24008177; PMCID: PMC3764307. 9: Kostova I. Coumarins as inhibitors of HIV reverse transcriptase. Curr HIV Res. 2006 Jul;4(3):347-63. doi: 10.2174/157016206777709393. PMID: 16842086. 10: Chidambaram S, El-Sheikh MA, Alfarhan AH, Radhakrishnan S, Akbar I. Synthesis of novel coumarin analogues: Investigation of molecular docking interaction of SARS-CoV-2 proteins with natural and synthetic coumarin analogues and their pharmacokinetics studies. Saudi J Biol Sci. 2021 Jan;28(1):1100-1108. doi: 10.1016/j.sjbs.2020.11.038. Epub 2020 Nov 12. PMID: 33199969; PMCID: PMC7658563.