Mer-NF5003F
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03216 |
| CAS | 149598-70-9 |
| Molecular Weight | 386.48 |
| Molecular Formula | C23H30O5 |
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Description
Mer-NF5003F is a myo-inositol monophosphatase (IMPase) inhibitor produced by Memnoniella echinata.
Specification
| Synonyms | Stachybotrydial; (2R,2'R,4a'S,6'R,8a'S)-4,6'-Dihydroxy-2',5',5',8a'-tetramethyl-3',4',4a',5',6',7',8',8a'-octahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde; Spiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6,7-dicarboxaldehyde, 3',4',4'a,5',6',7',8',8'a-octahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-, (2R,2'R,4a'S,6'R,8a'S)-; Spiro(benzofuran-2(3H),1'(2'H)-naphthalene)-6,7-dicarboxaldehyde, 3',4',4'a,5',6',7',8',8'a-octahydro-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-, (1'R-(1'alpha,2'alpha,4'aalpha,6'aalpha,8'aalpha))- |
| IUPAC Name | (3R,4aS,7R,8R,8aS)-3,4'-dihydroxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-3H-1-benzofuran]-6',7'-dicarbaldehyde |
| Canonical SMILES | CC1CCC2C(C(CCC2(C13CC4=C(C=C(C(=C4O3)C=O)C=O)O)C)O)(C)C |
| InChI | InChI=1S/C23H30O5/c1-13-5-6-18-21(2,3)19(27)7-8-22(18,4)23(13)10-15-17(26)9-14(11-24)16(12-25)20(15)28-23/h9,11-13,18-19,26-27H,5-8,10H2,1-4H3/t13-,18+,19-,22+,23-/m1/s1 |
| InChI Key | WIGGVNIABVHHCS-QJAXDWLUSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 551.5±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Antiviral and antiplasmodial spirodihydrobenzofuran terpenes from the fungus Stachybotrys nephrospora
Supaporn Sawadjoon, Yodhathai Thebtaranonth, Masahiko Isaka, Siribhorn Madla, Prasat Kittakoop, Kanyawim Kirtikara Planta Med . 2004 Nov;70(11):1085-7. doi: 10.1055/s-2004-832652.
Two known spirodihydrobenzofuran terpenes (1 and 2) were isolated from a mycelium extract of the fungus Stachybotrys nephrospora BCC 3900. Compound 1 (Mer-NF5003F or stachybotrydial) exhibited potent antiviral activity (the IC50 value of 4.32 microg/mL) comparable to the standard drug, acyclovir, while compound 2 was inactive against the HSV-1 virus. Both 1 and 2 possessed antiplasmodial activity (IC50 values of 0.85 and 0.15 microg/mL for 1 and 2, respectively), and were not toxic towards the Vero cell line. A regiospecific conversion of the dialdehyde 1 to the lactone 2 proceeded simply under acidic conditions.
2. Inhibitors of myo-inositol monophosphatase, ATCC 20928 factors A and C. Isolation, physico-chemical characterization and biological properties
S Stefanelli, C Sottani, C Brunati, K Islam, P Ferrari, E Corti, F Sponga J Antibiot (Tokyo) . 1996 Jul;49(7):611-6. doi: 10.7164/antibiotics.49.611.
During the course of a screening program for inhibitors of myo-inositol monophosphatase we fermented the strain ATCC 20928, a known producer of L-671,776. We now show that this strain produces a complex of at least three sesquiterpenic compounds, L-671,776 (termed factor B) and two structurally related substances, termed factors A and C. Both factors A and C, like L-671,776, exhibited inhibitory activity against myo-inositol monophosphatase. Six other fungi producing the above mentioned compounds were also isolated and taxonomically characterized.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
