NP-MRD: Showing NP-Card for (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0184955)

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Record Information

Version

1.0

Created at

2022-09-04 00:13:21 UTC

Updated at

2022-09-04 00:13:21 UTC

NP-MRD ID

NP0184955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

Description

Pseurotin A belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Pseurotin A 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. (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one is found in Aspergillus fumigatus, Aspergillus insulicola, Cordyceps tenuipes, Penicillium canescens and Pochonia chlamydosporia. It was first documented in 2020 (PMID: 32438039). Based on a literature review a significant number of articles have been published on pseurotin A (PMID: 35333152) (PMID: 35183746) (PMID: 34927009) (PMID: 34576982).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202132D          

 31 33  0  0  1  0            999 V2000
   -3.6821    0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5074    0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3596    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 19 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    5.2556    0.4727    2.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    1.4351    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.9170    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    1.7124   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.9940   -1.3662 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4319    1.7913   -2.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381    0.5904   -2.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8581    1.8085   -2.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -0.2848   -1.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508   -1.5115   -2.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135   -2.2614   -3.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1330   -2.0229   -1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187   -3.2202   -1.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2665   -0.8614   -0.2758 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7393    0.0964   -0.5257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4324   -1.1480    1.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.2068    2.1040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.3356    1.4576 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912   -1.2153    0.3139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6157   -2.4280   -0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -3.3994    0.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8235   -0.6117    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8098   -1.2116   -0.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.5671    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1742    1.2885    1.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859    2.4404    2.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7838    2.8792    2.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7639    2.1644    2.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4303    1.0363    1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6528   -0.3311   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9404   -0.6048   -1.9397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437   -0.5524    1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598    0.7776    3.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    0.3922    2.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027    1.0468    0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    2.3495    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632    2.4568    1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9391    2.0897   -0.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495    0.0940   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7402    2.5649   -1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    0.1506   -3.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8813    1.7531   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0616   -3.1389   -3.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597   -1.6581   -4.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7182   -2.7128   -2.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9681   -2.0477    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346   -4.3650   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709   -3.6025    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235   -3.1528    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1326    1.0241    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7334    3.0182    3.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0310    3.7859    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7777    2.5184    2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    0.4882    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    0.7290   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091   -1.5483   -2.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  1
 14 30  1  0
 30 31  1  0
 30 19  1  0
 19 20  1  6
 20 21  1  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 15  9  1  0
 29 24  1  0
 16 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  1
  6 40  1  0
  7 41  1  6
  8 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 30 55  1  1
 31 56  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 17 46  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
M  END


  Mrv1652309042202132D          

 31 33  0  0  1  0            999 V2000
   -3.6821    0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5074    0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3596    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 19 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0184955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/[C@H](O)[C@H](O)C1=C(C)C(=O)[C@@]2(O1)[C@@H](O)[C@@](OC)(N=C2O)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO8/c1-4-5-11-14(24)15(25)16-12(2)17(26)21(31-16)19(28)22(30-3,23-20(21)29)18(27)13-9-7-6-8-10-13/h5-11,14-15,19,24-25,28H,4H2,1-3H3,(H,23,29)/b11-5-/t14-,15-,19+,21+,22+/m0/s1

> <INCHI_KEY>
SLYDIPAXCVVRNY-UOWMTANKSA-N

> <FORMULA>
C22H25NO8

> <MOLECULAR_WEIGHT>
431.441

> <EXACT_MASS>
431.158016769

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.456766781358205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

> <JCHEM_LOGP>
2.053746247666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.099142905034864

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4666714319951755

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3677757468889364

> <JCHEM_POLAR_SURFACE_AREA>
145.88

> <JCHEM_REFRACTIVITY>
110.92160000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.873   1.600   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.466   0.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.305  -0.558   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.899  -1.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.653  -0.279   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.814   1.253   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.085  -2.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.941   3.481   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.275   2.016   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.799   3.481   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       4.740   1.540   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.271   0.161   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.898   1.568   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.060  -1.506   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.915  -2.537   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.524  -1.982   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.669  -0.952   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.134  -1.428   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.454  -2.934   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.309  -3.964   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.845  -3.489   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   30                                             
CONECT   15   14    9                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   22   30                                             
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   19   14   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Pseurotin	ChEBI

Chemical Formula

C₂₂H₂₅NO₈

Average Mass

431.4410 Da

Monoisotopic Mass

431.15802 Da

IUPAC Name

(5R,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

Traditional Name

(5R,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

CAS Registry Number

Not Available

SMILES

CC\C=C/[C@H](O)[C@H](O)C1=C(C)C(=O)[C@@]2(O1)[C@@H](O)[C@@](OC)(N=C2O)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C22H25NO8/c1-4-5-11-14(24)15(25)16-12(2)17(26)21(31-16)19(28)22(30-3,23-20(21)29)18(27)13-9-7-6-8-10-13/h5-11,14-15,19,24-25,28H,4H2,1-3H3,(H,23,29)/b11-5-/t14-,15-,19+,21+,22+/m0/s1

InChI Key

SLYDIPAXCVVRNY-UOWMTANKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 fumigatus	LOTUS Database	35616633
Aspergillus insulicola	LOTUS Database	35616633
Cordyceps tenuipes	LOTUS Database	35616633
Penicillium canescens	LOTUS Database	35616633
Pochonia chlamydosporia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Monocyclic benzene moiety
3-furanone
Pyrrolidone
2-pyrrolidone
Benzenoid
Dihydrofuran
Pyrrolidine
Vinylogous ester
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lactam (CHEBI:64535 )
azaspiro compound (CHEBI:64535 )
oxaspiro compound (CHEBI:64535 )

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	2.05	ChemAxon
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.88 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.92 m³·mol⁻¹	ChemAxon
Polarizability	43.46 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045032

Chemspider ID

8021336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pseurotin A

METLIN ID

Not Available

PubChem Compound

9845622

PDB ID

Not Available

ChEBI ID

64535

Good Scents ID

Not Available

References

General References

Margalit A, Sheehan D, Carolan JC, Kavanagh K: Exposure to the Pseudomonas aeruginosa secretome alters the proteome and secondary metabolite production of Aspergillus fumigatus. Microbiology (Reading). 2022 Mar;168(3). doi: 10.1099/mic.0.001164. [PubMed:35333152 ]
Sbaraini N, Phan CS, Silva E Souza E, Perin APA, Rezaee H, Geremia F, da Silva Camargo M, Barbosa EG, Schrank A, Chooi YH, Staats CC: Intra-hemocoel injection of pseurotin A from Metarhizium anisopliae, induces dose-dependent reversible paralysis in the Greater Wax Moth (Galleria mellonella). Fungal Genet Biol. 2022 Apr;159:103675. doi: 10.1016/j.fgb.2022.103675. Epub 2022 Feb 17. [PubMed:35183746 ]
Abdelwahed KS, Siddique AB, Qusa MH, King JA, Souid S, Abd Elmageed ZY, El Sayed KA: PCSK9 Axis-Targeting Pseurotin A as a Novel Prostate Cancer Recurrence Suppressor Lead. ACS Pharmacol Transl Sci. 2021 Oct 5;4(6):1771-1781. doi: 10.1021/acsptsci.1c00145. eCollection 2021 Dec 10. [PubMed:34927009 ]
Kim HJ, Li XJ, Kim DC, Kim TK, Sohn JH, Kwon H, Lee D, Kim YC, Yim JH, Oh H: PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394. Molecules. 2021 Sep 10;26(18):5505. doi: 10.3390/molecules26185505. [PubMed:34576982 ]
Abdelwahed KS, Siddique AB, Mohyeldin MM, Qusa MH, Goda AA, Singh SS, Ayoub NM, King JA, Jois SD, El Sayed KA: Pseurotin A as a novel suppressor of hormone dependent breast cancer progression and recurrence by inhibiting PCSK9 secretion and interaction with LDL receptor. Pharmacol Res. 2020 Aug;158:104847. doi: 10.1016/j.phrs.2020.104847. Epub 2020 May 11. [PubMed:32438039 ]
LOTUS database [Link]

Showing NP-Card for (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0184955)

MOL for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D MOL for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D SDF for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D-SDF for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

PDB for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D PDB for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

SMILES for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

INCHI for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

Structure for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D Structure for NP0184955 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)