Terrecyclic Acid
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MedKoo CAT#: 112194

CAS#: 83058-94-0

Description: Terrecyclic acid has antibiotic and anticancer activity.

Chemical Structure

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Terrecyclic Acid
CAS# 83058-94-0
Instruction

Theoretical Analysis

MedKoo Cat#: 112194
Name: Terrecyclic Acid
CAS#: 83058-94-0
Chemical Formula: C15H20O3
Exact Mass: 248.14
Molecular Weight: 248.320
Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

Price and Availability

Size Price Availability Quantity
1mg USD 390 2 Weeks
5mg USD 1230 2 Weeks
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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:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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.


2: 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.


3: 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.


4: 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.


5: 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.


6: 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.


7: 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.