NP-MRD: Showing NP-Card for 8-benzoyl-2-(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 (NP0184298)

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Record Information

Version

2.0

Created at

2022-09-03 23:23:32 UTC

Updated at

2022-09-03 23:23:32 UTC

NP-MRD ID

NP0184298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-benzoyl-2-(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. While it is unknown how the azaspirocyclic core of the pseurotin family of natural products is made, the post polyketide synthase modifications are known. Pseurotin A is a secondary metabolite of Aspergillus. Pseurotin A is an extremely weak basic (essentially neutral) compound (based on its pKa). PsoC codes for a methyltransferase, which methylates the tertiary alcohol closest to the benzoyl moiety on C8. This epoxide is spontaneously hydrolyzed by either an SN2 mechanism to form pseurotin A, or by an SN2’ mechanism to form pseurotin D. PsoD codes for a cytochrome P450, which is responsible for oxidizing the benzyl carbon (C17) to the conjugated ketone. PsoF is unique in that its gene is encoded separate from the pseurotin gene cluster and is responsible for the epoxidation of the trans double bond that remains in the tail. PsoE is predicted to be a glutathione S-transferase gene, and isomerizes the CC bond furthest down the tail from the E stereoisomer to the Z stereoisomer. 8-benzoyl-2-(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 and Penicillium canescens. In-vivo and in-vitro studies showed the unique mechanism involved in the modification ezymes PsoC, PsoD, PsoE, and PsoF.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171508352D          

 31 33  0  0  0  0            999 V2000
   -4.2633   -0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5097   -0.7837    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  0  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  0  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  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  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
    2.8825    1.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    2.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    1.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    0.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700    0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8343   -1.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0147   -1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  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  0  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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    7.7637    0.0454    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1252    0.7199   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591    0.4409   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373   -0.3269    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5734   -0.5598    0.0003 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2710   -1.8251    0.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837    0.5354    0.7695 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2398    0.4934    2.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119    0.4849    0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    1.4733    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1892    2.7980   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222    1.0565    0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    1.8741    0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -0.4040    0.2801 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5501   -0.5713    0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -1.1220   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.9174   -1.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096   -2.0627   -1.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -1.4803   -0.1462 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6245   -2.4384    0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100   -2.8579   -0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3866   -0.3910   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985   -0.0583   -2.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052    0.3506   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0319    0.0585    0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0860    0.7885    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6629    1.8310    0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1357    2.1218   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0901    1.4001   -0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405   -0.9892    0.9954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3921   -2.1647    1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8386   -1.0378    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8001    0.4742    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2363    0.3556    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3500    1.7964   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5731    0.3232   -1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0633    0.8647   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6027   -0.7753    0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -0.4121   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -2.3639    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377    1.4894    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094    0.0062    2.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699    2.6127   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    3.5563   -0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242    3.1473    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -2.9698   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1567   -3.6220   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7746   -3.3242   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9145   -1.9948   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6555   -0.7307    1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4879    0.5384    2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4983    2.3944    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5846    2.9380   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7068    1.6756   -1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -0.3110    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9773   -2.9341    1.4482 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 18  1  0
 18 16  1  0
 16 17  2  0
 19 20  1  1
 20 21  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  6
  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
 18 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
M  END


  Mrv1533004171508352D          

 31 33  0  0  0  0            999 V2000
   -4.2633   -0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5097   -0.7837    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  0  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  0  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  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  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
    2.8825    1.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    2.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    1.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    0.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700    0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8343   -1.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0147   -1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -0.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  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  0  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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC=CC(O)C(O)C1=C(C)C(=O)C2(O1)C(O)C(NC2=O)(OC)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)

> <INCHI_KEY>
SLYDIPAXCVVRNY-UHFFFAOYSA-N

> <FORMULA>
C22H25NO8

> <MOLECULAR_WEIGHT>
431.441

> <EXACT_MASS>
431.158016769

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.304997998848236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-benzoyl-2-(1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.234142120666666

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.033941952458775

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.737819633312254

> <JCHEM_PKA_STRONGEST_BASIC>
-3.367776047333657

> <JCHEM_POLAR_SURFACE_AREA>
142.39000000000001

> <JCHEM_REFRACTIVITY>
110.39989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-benzoyl-2-(1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -7.958  -0.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.551  -1.463   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  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.740  -0.000   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.381   2.940   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.489   4.196   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.269   1.717   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.881   3.130   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.188   0.481   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.717   0.658   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.636  -0.579   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.024  -1.992   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.494  -2.169   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.576  -0.933   0.000  0.00  0.00           C+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   20                                             
CONECT   15   14    9                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Pseurotin	MeSH
Pseurotin a	MeSH

Chemical Formula

C₂₂H₂₅NO₈

Average Mass

431.4410 Da

Monoisotopic Mass

431.15802 Da

IUPAC Name

8-benzoyl-2-(1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Traditional Name

8-benzoyl-2-(1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

CAS Registry Number

Not Available

SMILES

CCC=CC(O)C(O)C1=C(C)C(=O)C2(O1)C(O)C(NC2=O)(OC)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)

InChI Key

SLYDIPAXCVVRNY-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, 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
Penicillium canescens	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

Not Available

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	1.37	ALOGPS
logP	1.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.39 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.4 m³·mol⁻¹	ChemAxon
Polarizability	43.3 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pseurotin A

METLIN ID

Not Available

PubChem Compound

434331

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-benzoyl-2-(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 (NP0184298)

MOL for NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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 NP0184298 (8-benzoyl-2-(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)