NP-MRD: Showing NP-Card for EQ-4 (NP0006275)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-12-09 03:18:40 UTC

Updated at

2021-07-15 16:54:20 UTC

NP-MRD ID

NP0006275

Secondary Accession Numbers

None

Natural Product Identification

Common Name

EQ-4

Provided By

NPAtlas

Description

(-)-Microperfuranone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. EQ-4 is found in Emericella quadrilineata, Emericella, Emericella nidulans var.acristata and Neurospora micropertusa. It was first documented in 2006 (PMID: 16595963). Based on a literature review a significant number of articles have been published on (-)-microperfuranone (PMID: 16872131) (PMID: 22627757) (PMID: 32526136) (PMID: 31963266) (PMID: 28262121) (PMID: 30452182).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118263D          

 34 36  0  0  0  0            999 V2000
    2.1966    3.3495    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    2.6634   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.1107   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.0344   -1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1410    2.0091   -2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    0.8273   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.5696   -0.9192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8124   -0.7607   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -0.5570   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.7166   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -1.0864    0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -1.2931    1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408   -1.1311    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.1988   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.3147    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5494    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.2482    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.3318    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.5839   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -0.7707   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    2.0760   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    2.9304   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -0.7897   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.3064   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317   -0.2617   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -0.5377   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362   -1.2049    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597   -1.5816    2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -1.2896    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.3867    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.0088    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.9418    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -2.4456   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023   -1.0336   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14  2  1  0  0  0  0
 20 15  1  0  0  0  0
 13  8  1  0  0  0  0
  4 21  1  1  0  0  0
  5 22  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.1966    3.3495    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    2.6634   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.1107   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.0344   -1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1410    2.0091   -2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    0.8273   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.5696   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.7607   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -0.5570   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.7166   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -1.0864    0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -1.2931    1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408   -1.1311    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.1988   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.3147    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5494    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.2482    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.3318    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.5839   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -0.7707   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    2.0760   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    2.9304   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -0.7897   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.3064   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317   -0.2617   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -0.5377   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362   -1.2049    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597   -1.5816    2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -1.2896    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.3867    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.0088    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.9418    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -2.4456   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023   -1.0336   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  8  1  0
  4 21  1  1
  5 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652306242118263D          

 34 36  0  0  0  0            999 V2000
    2.1966    3.3495    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    2.6634   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.1107   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.0344   -1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1410    2.0091   -2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    0.8273   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.5696   -0.9192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8124   -0.7607   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -0.5570   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.7166   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -1.0864    0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -1.2931    1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408   -1.1311    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.1988   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.3147    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5494    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.2482    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.3318    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.5839   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -0.7707   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    2.0760   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    2.9304   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -0.7897   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.3064   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317   -0.2617   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -0.5377   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362   -1.2049    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597   -1.5816    2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -1.2896    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.3867    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.0088    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.9418    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -2.4456   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023   -1.0336   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14  2  1  0  0  0  0
 20 15  1  0  0  0  0
 13  8  1  0  0  0  0
  4 21  1  1  0  0  0
  5 22  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006275

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])OC(=O)C(=C1C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O3/c18-16-14(11-12-7-3-1-4-8-12)15(17(19)20-16)13-9-5-2-6-10-13/h1-10,16,18H,11H2/t16-/m1/s1

> <INCHI_KEY>
MFURXTOJWOOSEM-UHFFFAOYSA-N

> <FORMULA>
C17H14O3

> <MOLECULAR_WEIGHT>
266.296

> <EXACT_MASS>
266.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.248631853483346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-4-benzyl-5-hydroxy-3-phenyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.6622133516666664

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.451109954197008

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.561728156628034

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287201643466909

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
75.70740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-4-benzyl-5-hydroxy-3-phenyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.1966    3.3495    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    2.6634   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.1107   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.0344   -1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1410    2.0091   -2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    0.8273   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.5696   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.7607   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -0.5570   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.7166   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -1.0864    0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -1.2931    1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408   -1.1311    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.1988   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.3147    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5494    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.2482    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.3318    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.5839   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -0.7707   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    2.0760   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    2.9304   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -0.7897   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.3064   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317   -0.2617   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -0.5377   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362   -1.2049    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597   -1.5816    2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -1.2896    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.3867    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.0088    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.9418    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -2.4456   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023   -1.0336   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  8  1  0
  4 21  1  1
  5 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       2.197   3.349   0.060  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.204   2.663  -0.343  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.032   3.111  -0.870  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.789   2.034  -1.188  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.141   2.009  -2.543  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.030   0.827  -0.802  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.528  -0.570  -0.919  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.812  -0.761  -0.218  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.974  -0.557  -0.933  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.219  -0.717  -0.356  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.329  -1.086   0.959  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.200  -1.293   1.686  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.941  -1.131   1.100  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.130   1.199  -0.314  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.201   0.315   0.152  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.851   0.549   1.346  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.879  -0.248   1.807  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.298  -1.332   1.070  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.662  -1.584  -0.124  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.630  -0.771  -0.574  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.709   2.076  -0.556  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.470   2.930  -2.747  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.688  -0.790  -1.990  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.168  -1.306  -0.460  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.932  -0.262  -1.981  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.101  -0.538  -0.989  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.336  -1.205   1.392  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.260  -1.582   2.716  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.023  -1.290   1.657  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.563   1.387   1.964  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.351  -0.009   2.757  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.106  -1.942   1.457  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.008  -2.446  -0.692  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.202  -1.034  -1.525  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   21                                             
CONECT    5    4   22                                                       
CONECT    6    4    7   14                                                  
CONECT    7    6    8   23   24                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12    8   29                                                  
CONECT   14    6   15    2                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   15   34                                                  
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
    2.1966    3.3495    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    2.6634   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.1107   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.0344   -1.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1410    2.0091   -2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    0.8273   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.5696   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.7607   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -0.5570   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.7166   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -1.0864    0.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -1.2931    1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408   -1.1311    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.1988   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.3147    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5494    1.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.2482    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.3318    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.5839   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -0.7707   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    2.0760   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    2.9304   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -0.7897   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.3064   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317   -0.2617   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -0.5377   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362   -1.2049    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597   -1.5816    2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -1.2896    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.3867    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.0088    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -1.9418    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -2.4456   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023   -1.0336   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  8  1  0
  4 21  1  1
  5 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-4-Benzyl-5-hydroxy-3-phenylfuran-2(5H)-one	ChEBI
Microperfuranone	ChEBI

Chemical Formula

C₁₇H₁₄O₃

Average Mass

266.2960 Da

Monoisotopic Mass

266.09429 Da

IUPAC Name

(5R)-4-benzyl-5-hydroxy-3-phenyl-2,5-dihydrofuran-2-one

Traditional Name

(5R)-4-benzyl-5-hydroxy-3-phenyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

OC1OC(=O)C(=C1CC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14O3/c18-16-14(11-12-7-3-1-4-8-12)15(17(19)20-16)13-9-5-2-6-10-13/h1-10,16,18H,11H2

InChI Key

MFURXTOJWOOSEM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus quadrilineatus	-	KNApSAcK
Emericella	NPAtlas	16595963
Emericella nidulans var.acristata	-	KNApSAcK
Neurospora micropertusa	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.93	ALOGPS
logP	3.66	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.71 m³·mol⁻¹	ChemAxon
Polarizability	28.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016720

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8739070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10563682

PDB ID

Not Available

ChEBI ID

64974

Good Scents ID

Not Available

References

General References

Fujimoto H, Asai T, Kim YP, Ishibashi M: Nine constituents including six xanthone-related compounds isolated from two ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity. Chem Pharm Bull (Tokyo). 2006 Apr;54(4):550-3. doi: 10.1248/cpb.54.550. [PubMed:16595963 ]
Kralj A, Kehraus S, Krick A, Eguereva E, Kelter G, Maurer M, Wortmann A, Fiebig HH, Konig GM: Arugosins G and H: prenylated polyketides from the marine-derived fungus Emericellanidulans var. acristata. J Nat Prod. 2006 Jul;69(7):995-1000. doi: 10.1021/np050454f. [PubMed:16872131 ]
Yeh HH, Chiang YM, Entwistle R, Ahuja M, Lee KH, Bruno KS, Wu TK, Oakley BR, Wang CC: Molecular genetic analysis reveals that a nonribosomal peptide synthetase-like (NRPS-like) gene in Aspergillus nidulans is responsible for microperfuranone biosynthesis. Appl Microbiol Biotechnol. 2012 Nov;96(3):739-48. doi: 10.1007/s00253-012-4098-9. Epub 2012 May 25. [PubMed:22627757 ]
Roux I, Woodcraft C, Hu J, Wolters R, Gilchrist CLM, Chooi YH: CRISPR-Mediated Activation of Biosynthetic Gene Clusters for Bioactive Molecule Discovery in Filamentous Fungi. ACS Synth Biol. 2020 Jul 17;9(7):1843-1854. doi: 10.1021/acssynbio.0c00197. Epub 2020 Jun 26. [PubMed:32526136 ]
Kim MJ, Lee MK, Pham HQ, Gu MJ, Zhu B, Son SH, Hahn D, Shin JH, Yu JH, Park HS, Han KH: The velvet Regulator VosA Governs Survival and Secondary Metabolism of Sexual Spores in Aspergillus nidulans. Genes (Basel). 2020 Jan 16;11(1). pii: genes11010103. doi: 10.3390/genes11010103. [PubMed:31963266 ]
An X, Feng BM, Chen G, Chen SF, Wang HF, Pei YH: Isolation and identification of two new compounds from marine-derived fungus Acremonium fusidioides RZ01. Chin J Nat Med. 2016 Dec;14(12):934-938. doi: 10.1016/S1875-5364(17)30019-5. [PubMed:28262121 ]
Furukawa T, Fukuda T, Nagai K, Uchida R, Tomoda H: Helvafuranone Produced by the Fungus Aspergillus nidulans BF0142 Isolated from Hot Spring-derived Soil. Nat Prod Commun. 2016 Jul;11(7):1001-1003. [PubMed:30452182 ]

Showing NP-Card for EQ-4 (NP0006275)

MOL for NP0006275 (EQ-4)

3D MOL for NP0006275 (EQ-4)

3D SDF for NP0006275 (EQ-4)

3D-SDF for NP0006275 (EQ-4)

PDB for NP0006275 (EQ-4)

3D PDB for NP0006275 (EQ-4)

SMILES for NP0006275 (EQ-4)

INCHI for NP0006275 (EQ-4)

Structure for NP0006275 (EQ-4)

3D Structure for NP0006275 (EQ-4)