MedKoo Cat#: 581112 | Name: Netzahualcoyonol

Description:

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

Netzahualcoyonol, the crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-hydroxyfriedelan-3-one. The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.

Chemical Structure

Netzahualcoyonol
Netzahualcoyonol
CAS#113579-07-0

Theoretical Analysis

MedKoo Cat#: 581112

Name: Netzahualcoyonol

CAS#: 113579-07-0

Chemical Formula: C30H38O5

Exact Mass: 478.2719

Molecular Weight: 478.63

Elemental Analysis: C, 75.28; H, 8.00; O, 16.71

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
Netzahualcoyonol;
IUPAC/Chemical Name
methyl (2R,3R,4aS,12bR,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate
InChi Key
AKILTDMBUDIAST-SMVJIKPISA-N
InChi Code
InChI=1S/C30H38O5/c1-16-13-27(3)15-23(32)30(6,26(34)35-7)14-22(27)29(5)11-10-28(4)19(24(16)29)9-8-18-17(2)25(33)21(31)12-20(18)28/h8-9,12,22-23,32-33H,10-11,13-15H2,1-7H3/t22-,23+,27-,28-,29-,30+/m0/s1
SMILES Code
O[C@H](C1)[C@](C)(C(OC)=O)C[C@H]2[C@@]1(C)CC(C)=C3[C@@]2(C)CC[C@](C)(C4=C5)C3=CC=C4C(C)=C(O)C5=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 478.63 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: Setzer WN, Holland MT, Bozeman CA, Rozmus GF, Setzer MC, Moriarity DM, Reeb S, Vogler B, Bates RB, Haber WA. Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis. Planta Med. 2001 Feb;67(1):65-9. PubMed PMID: 11270725.