MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 574256 | Name: Terpendole C
Featured

Description:

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

Terpendole C is an indole diterpene alkaloid fungal metabolite and inhibitor of acyl-coenzyme A:cholesterol acyltransferase (ACAT). It also inhibits ACAT in J774 macrophages without affecting cell growth.

Chemical Structure

Terpendole C
Terpendole C
CAS#156967-65-6

Theoretical Analysis

MedKoo Cat#: 574256

Name: Terpendole C

CAS#: 156967-65-6

Chemical Formula: C32H41NO5

Exact Mass: 519.2985

Molecular Weight: 519.68

Elemental Analysis: C, 73.96; H, 7.95; N, 2.70; O, 15.39

Price and Availability

Size Price Availability Quantity
1mg USD 575.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Terpendole C
IUPAC/Chemical Name
(3S,4aR,4bR,5aS,5bS,7aS,13bS,13cR,15aS,16aS)-1,1,13b,13c-tetramethyl-3-(2-methylprop-1-en-1-yl)-1,4a,4b,6,7,7a,8,13,13b,13c,14,15,15a,16a-tetradecahydro-5bH-[1,3]dioxino[5'',4'':2',3']oxireno[2'',3'':4',4a']chromeno[5',6':6,7]indeno[1,2-b]indol-5b-ol
InChi Key
WUOATFFODCBZBE-SCGIUCFSSA-N
InChi Code
InChI=1S/C32H41NO5/c1-17(2)15-23-36-24-26(28(3,4)37-23)35-22-12-13-29(5)30(6)18(11-14-31(29,34)32(22)27(24)38-32)16-20-19-9-7-8-10-21(19)33-25(20)30/h7-10,15,18,22-24,26-27,33-34H,11-14,16H2,1-6H3/t18-,22-,23-,24+,26-,27+,29+,30+,31-,32-/m0/s1
SMILES Code
C/C(C)=C/[C@@H]1OC(C)(C)[C@@]2([H])O[C@@]3([H])CC[C@@]4(C)[C@](CC[C@]5([H])[C@]4(C)C6=C(C(C=CC=C7)=C7N6)C5)(O)[C@@]3(O8)[C@H]8[C@]2([H])O1
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 519.68 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: Vassiliadis S, Reddy P, Hemsworth J, Spangenberg GC, Guthridge KM, Rochfort SJ. Quantitation and Distribution of Epichloë-Derived Alkaloids in Perennial Ryegrass Tissues. Metabolites. 2023 Jan 30;13(2):205. doi: 10.3390/metabo13020205. PMID: 36837825; PMCID: PMC9966479. 2: Dai Z, Gan Y, Zhao P, Li G. Secondary Metabolites from the Endoparasitic Nematophagous Fungus Harposporium anguillulae YMF 1.01751. Microorganisms. 2022 Jul 31;10(8):1553. doi: 10.3390/microorganisms10081553. PMID: 36013971; PMCID: PMC9415808. 3: Zabaleta G, Lee ST, Cook D, Aguilar M, Iannone LJ, Robles C, Martinez A. Indole-diterpenes alkaloid profiles of native grasses involved in tremorgenic syndromes in the Argentine Patagonia. Toxicon. 2022 Oct 15;217:107-111. doi: 10.1016/j.toxicon.2022.08.001. Epub 2022 Aug 15. PMID: 35981666. 4: Fernando K, Reddy P, Vassiliadis S, Spangenberg GC, Rochfort SJ, Guthridge KM. The Known Antimammalian and Insecticidal Alkaloids Are Not Responsible for the Antifungal Activity of Epichloë Endophytes. Plants (Basel). 2021 Nov 17;10(11):2486. doi: 10.3390/plants10112486. PMID: 34834850; PMCID: PMC8624124. 5: Gardner DR, Welch KD, Lee ST, Cook D, Riet-Correa F. Tremorgenic Indole Diterpenes from Ipomoea asarifolia and Ipomoea muelleri and the Identification of 6,7-Dehydro-11-hydroxy-12,13-epoxyterpendole A. J Nat Prod. 2018 Jul 27;81(7):1682-1686. doi: 10.1021/acs.jnatprod.8b00257. Epub 2018 Jul 16. PMID: 30011204. 6: Ohshiro T, Rudel LL, Omura S, Tomoda H. Selectivity of microbial acyl-CoA: cholesterol acyltransferase inhibitors toward isozymes. J Antibiot (Tokyo). 2007 Jan;60(1):43-51. doi: 10.1038/ja.2007.6. PMID: 17390588. 7: Gatenby WA, Munday-Finch SC, Wilkins AL, Miles CO. Terpendole M, a novel indole-diterpenoid isolated from Lolium perenne infected with the endophytic fungus Neotyphodium lolii. J Agric Food Chem. 1999 Mar;47(3):1092-7. doi: 10.1021/jf980767z. PMID: 10552421. 8: Huang XH, Nishida H, Tomoda H, Tabata N, Shiomi K, Yang DJ, Takayanagi H, Omura S. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D. J Antibiot (Tokyo). 1995 Jan;48(1):5-11. doi: 10.7164/antibiotics.48.5. Erratum in: J Antibiot (Tokyo) 1995 Mar;48(3):C-1. PMID: 7868389. 9: Huang XH, Tomoda H, Nishida H, Masuma R, Omura S. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. I. Production, isolation and biological properties. J Antibiot (Tokyo). 1995 Jan;48(1):1-4. doi: 10.7164/antibiotics.48.1. Erratum in: J Antibiot (Tokyo) 1995 Mar;48(3):C-1. PMID: 7868384.