Terrecyclic Acid | CAS#83058-94-0 | Antibiotic & Anticancer agent| MedKoo

MedKoo Cat#: 112194 | Name: Terrecyclic Acid

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Description:

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

Terrecyclic acid is a fungal quadrane which has antibiotic and anticancer activity.

Chemical Structure

Terrecyclic Acid

CAS#83058-94-0

Theoretical Analysis

MedKoo Cat#: 112194

Name: Terrecyclic Acid

CAS#: 83058-94-0

Chemical Formula: C15H20O3

Exact Mass: 248.1412

Molecular Weight: 248.32

Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00	2 Weeks
5mg	USD 1,350.00	2 Weeks

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Related CAS #

No Data

Synonym

Terrecyclic Acid

IUPAC/Chemical Name

(3aS,4R,7R,7aR)-8,8-dimethyl-3-methylene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid

InChi Key

SMAWCSOVJJHIOI-JNIYBQFBSA-N

InChi Code

InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m1/s1

SMILES Code

O=C1C([C@@]23[C@@H](CC[C@]([H])([C@]3(C1)[H])C(C)(C2)C)C(O)=O)=C

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 248.32 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.

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: Song Y, Wang W, Yang J, Gao D, Billingsley JM, Wang S, Zhu Y, Wang J, Ju J, Yan Y, Tang Y. β-Terrecyclene synthase constructs the quadrane backbone in terrecyclic acid biosynthesis. Chem Sci. 2024 Apr 25;15(23):8750-8755. doi: 10.1039/d4sc01208a. PMID: 38873062; PMCID: PMC11168084. 2: Wu T, Salim AA, Bernhardt PV, Capon RJ. Molecular Networking and Cultivation Profiling Reveals Diverse Natural Product Classes from an Australian Soil- Derived Fungus Aspergillus sp. CMB-MRF324. Molecules. 2022 Dec 19;27(24):9066. doi: 10.3390/molecules27249066. PMID: 36558198; PMCID: PMC9786664. 3: Barquera-Lozada JE, Cuevas G. Role of carbocation's flexibility in sesquiterpene biosynthesis: computational study of the formation mechanism of terrecyclene. J Org Chem. 2011 Mar 18;76(6):1572-7. doi: 10.1021/jo101869z. Epub 2011 Feb 22. PMID: 21338132. 4: Turbyville TJ, Wijeratne EM, Whitesell L, Gunatilaka AA. The anticancer activity of the fungal metabolite terrecyclic acid A is associated with modulation of multiple cellular stress response pathways. Mol Cancer Ther. 2005 Oct;4(10):1569-76. doi: 10.1158/1535-7163.MCT-05-0050. PMID: 16227407. 5: Wijeratne EM, Turbyville TJ, Zhang Z, Bigelow D, Pierson LS 3rd, VanEtten HD, Whitesell L, Canfield LM, Gunatilaka AA. Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert. J Nat Prod. 2003 Dec;66(12):1567-73. doi: 10.1021/np030266u. PMID: 14695798. 6: Almassi F, Ghisalberti EL, Skelton BW, White AH. Molecular structure of terrecyclodiol: a derivative of the antifungal metabolite terrecyclic acid A from Aspergillus terreus. J Nat Prod. 1996 Jan;59(1):59-61. doi: 10.1021/np960008f. PMID: 8984154. 7: Hirota A, Nakagawa M, Hirota H, Takahashi T, Isogai A. Terrecyclic acid A, a new antibiotic from Aspergillus terreus. IV. Absolute stereochemistry of terrecyclic acid A. J Antibiot (Tokyo). 1986 Jan;39(1):149-52. doi: 10.7164/antibiotics.39.149. PMID: 3949627. 8: Beale JM Jr, Chapman RL, Rosazza JP. Studies on the biosynthesis of terrecyclic acid A, an antitumor antibiotic from Aspergillus terreus. J Antibiot (Tokyo). 1984 Nov;37(11):1376-81. doi: 10.7164/antibiotics.37.1376. PMID: 6511664. 9: Hirota A, Nakagawa M, Sakai H, Isogai A. Terrecyclic acid A, a new antibiotic from Aspergillus terreus. III. 13C NMR spectrum of terrecyclic acid A. J Antibiot (Tokyo). 1984 May;37(5):475-8. doi: 10.7164/antibiotics.37.475. PMID: 6735922. 10: Hirota A, Nakagawa M, Sakai H, Isogai A. Terrecyclic acid A, a new antibiotic from Aspergillus terreus. II. Structure of terrecyclic acid A. J Antibiot (Tokyo). 1982 Jul;35(7):783-7. doi: 10.7164/antibiotics.35.783. PMID: 7174532. 11: Nakagawa M, Hirota A, Sakai H, Isogai A. Terrecyclic acid A, a new antibiotic from Aspergillus terreus. I. Taxonomy, production, and chemical and biological properties. J Antibiot (Tokyo). 1982 Jul;35(7):778-82. doi: 10.7164/antibiotics.35.778. PMID: 7174531.