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

MedKoo CAT#: 585061

CAS#: 78777-02-3

Description: 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

CAS# 78777-02-3

Theoretical Analysis

MedKoo Cat#: 585061
Name: Ptilocaulin
CAS#: 78777-02-3
Chemical Formula: C15H25N3
Exact Mass: 247.2048
Molecular Weight: 247.386
Elemental Analysis: C, 72.83; H, 10.19; N, 16.99

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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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 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

Preparing Stock Solutions

The following data is based on the product molecular weight 247.386 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

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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.