Synonym
(−)-Verrucofortine, Fructigenine B, Verrucofortine, Verrucozine
IUPAC/Chemical Name
(3S,5aR,10bR,11aS)-6-acetyl-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
InChi Key
BMRZKNPRSPWNNW-UNBWHIKDSA-N
InChi Code
InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)/t17-,19-,22-,24+/m0/s1
SMILES Code
CC([C@]12C3=CC=CC=C3N(C(C)=O)[C@]1(N([C@](C2)([H])C(N4)=O)C([C@@H]4CC(C)C)=O)[H])(C=C)C
Purity
>99% (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
409.53
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: Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M. Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine- derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. PMID: 26243556.
2: Santini A, Mikušová P, Sulyok M, Krska R, Labuda R, Srobárová A. Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile. Mycotoxin Res. 2014 Nov;30(4):213-20. doi: 10.1007/s12550-014-0205-3. Epub 2014 Aug 12. PMID: 25109845.
3: Núñez F, Westphal CD, Bermúdez E, Asensio MA. Production of secondary metabolites by some terverticillate penicillia on carbohydrate-rich and meat substrates. J Food Prot. 2007 Dec;70(12):2829-36. doi: 10.4315/0362-028x-70.12.2829. PMID: 18095438.
4: Nielsen KF. Mycotoxins from mould infested building materials. Mycotoxin Res. 2000 Mar;16 Suppl 1:113-6. doi: 10.1007/BF02942996. PMID: 23605430.
5: Nielsen KF, Gravesen S, Nielsen PA, Andersen B, Thrane U, Frisvad JC. Production of mycotoxins on artificially and naturally infested building materials. Mycopathologia. 1999;145(1):43-56. doi: 10.1023/a:1007038211176. PMID: 10560628.
6: Hodge RP, Harris CM, Harris TM. Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin. J Nat Prod. 1988 Jan-Feb;51(1):66-73. doi: 10.1021/np50055a008. PMID: 3373229.
