Ptilocaulin | CAS#78777-02-3 | antimicrobial

MedKoo Cat#: 585061 | Name: Ptilocaulin

Description:

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

Ptilocaulin is a cyclic guanidine extracted from the Caribbean sponge Ptilocaulis aff. P. Spiculifer that is reported to have broad spectrum antimicrobial activity in vitro as well as in vitro activity against L1210 murine leukemia.

Chemical Structure

Ptilocaulin

CAS#78777-02-3

Theoretical Analysis

MedKoo Cat#: 585061

Name: Ptilocaulin

CAS#: 78777-02-3

Chemical Formula: C15H25N3

Exact Mass: 247.2048

Molecular Weight: 247.39

Elemental Analysis: C, 72.83; H, 10.19; N, 16.99

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ptilocaulin; Isoptilocauline

IUPAC/Chemical Name

Cyclopenta(de)quinazolin-2-amine, 8-butyl-1,3a,4,5,5a,6,7,8b-octahydro-7-methyl-, (3aS-(3aalpha,5aalpha,7alpha,8balpha))-

InChi Key

MGZKFJKGMKJURC-XRRVDJEJSA-N

InChi Code

InChI=1S/C15H25N3/c1-3-4-5-11-9(2)8-10-6-7-12-13(10)14(11)18-15(16)17-12/h9-10,12-13H,3-8H2,1-2H3,(H3,16,17,18)/t9-,10-,12-,13+/m0/s1

SMILES Code

NC1=N[C@]2([H])[C@@]3([H])[C@](CC2)([H])C[C@H](C)C(CCCC)=C3N1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 247.39 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: Santos MF, Harper PM, Williams DE, Mesquita JT, Pinto ÉG, da Costa-Silva TA, Hajdu E, Ferreira AG, Santos RA, Murphy PJ, Andersen RJ, Tempone AG, Berlinck RG. Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. J Nat Prod. 2015 May 22;78(5):1101-12. doi: 10.1021/acs.jnatprod.5b00070. Epub 2015 Apr 29. PubMed PMID: 25924111. 2: Yu M, Pochapsky SS, Snider BB. Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G. J Org Chem. 2008 Nov 21;73(22):9065-74. doi: 10.1021/jo801956w. Epub 2008 Oct 18. PubMed PMID: 18928319; PubMed Central PMCID: PMC2593083. 3: Gallimore WA, Kelly M, Scheuer PJ. Alkaloids from the sponge Monanchora unguifera. J Nat Prod. 2005 Sep;68(9):1420-3. PubMed PMID: 16180828. 4: Ruben RL, Snider BB, Hobbs FW Jr, Confalone PN, Dusak BA. Cytotoxicity of synthetic racemic ptilocaulin: a novel cyclic guanidine. Invest New Drugs. 1989 Jul;7(2-3):147-54. PubMed PMID: 2793367.