NP-MRD: Showing NP-Card for 14-norpseurotin A (NP0007799)

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Record Information

Version

2.0

Created at

2020-12-09 04:34:50 UTC

Updated at

2021-07-15 16:58:35 UTC

NP-MRD ID

NP0007799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-norpseurotin A

Provided By

NPAtlas

Description

14-Norpseurotin 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. 14-Norpseurotin 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. 14-norpseurotin A is found in Aspergillus, Aspergillus fumigatus, Cordyceps tenuipes and Isaria tenuipes BCC12625. 14-norpseurotin A was first documented in 2008 (PMID: 18505285). Based on a literature review very few articles have been published on 14-norpseurotin A (PMID: 22474943).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106043D          

 53 55  0  0  0  0            999 V2000
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    4.4304    0.0498   -1.0143 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242106043D          

 53 55  0  0  0  0            999 V2000
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    3.2050   -3.0204    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -3.4325   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    2.6917    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -1.7550    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9048   -2.0032    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -2.3041    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8191    0.0608    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1923   -0.3779    1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2730    0.1167   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120    1.0118   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920    1.4078   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    0.7002   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.3120   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14  8  1  0  0  0  0
 28 23  1  0  0  0  0
 29 13  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  1  0  0  0
  5 37  1  0  0  0  0
  6 38  1  1  0  0  0
  7 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 17 43  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
 27 50  1  0  0  0  0
 28 51  1  0  0  0  0
 29 52  1  6  0  0  0
 30 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007799

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO8/c1-4-8-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29-3,22-19(20)28)17(26)12-9-6-5-7-10-12/h4-10,13-14,18,23-24,27H,1-3H3,(H,22,28)/b8-4-/t13-,14-,18+,20+,21+/m0/s1

> <INCHI_KEY>
FCGCMRDADMTJIM-LFDIKFNASA-N

> <FORMULA>
C21H23NO8

> <MOLECULAR_WEIGHT>
417.414

> <EXACT_MASS>
417.142366705

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.04706350913037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-3-en-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
0.7895734556666661

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.034362873111357

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.795595227926292

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3671641915522983

> <JCHEM_POLAR_SURFACE_AREA>
142.39000000000001

> <JCHEM_REFRACTIVITY>
105.79890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-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

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    6.2854    2.2270   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    2.4436   -1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    1.4401   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4304    0.0498   -1.0143 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4522   -0.2496   -1.9181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -0.9109   -1.1823 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7171   -0.8450   -2.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -0.7042   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -1.6564    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496   -3.0586    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.0756    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601   -1.5184    2.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518    0.1112    0.8732 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5156    0.4702    0.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439    1.2287    1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868    1.6762    2.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926    1.7248    1.3396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.4898    0.8496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2724   -0.3201    1.8536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -1.6171    1.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.9636   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366    1.7568   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4296    0.7569   -0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2443    0.2600    0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6104    0.0227    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028    0.2939   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363    0.7948   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009    1.0137   -1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -0.0593    0.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0649   -1.2997   -0.5077 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765    1.7295   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052    1.6402    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7724    3.2276   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185    3.4510   -1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    1.6457   -1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -0.1138    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1704   -0.7769   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172   -1.9283   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565   -1.3547   -3.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -3.7130    1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -3.0204    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -3.4325   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    2.6917    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -1.7550    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9048   -2.0032    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -2.3041    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8191    0.0608    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1923   -0.3779    1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2730    0.1167   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120    1.0118   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920    1.4078   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    0.7002   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.3120   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 18 29  1  0
 29 30  1  0
 14  8  1  0
 28 23  1  0
 29 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  1
  5 37  1  0
  6 38  1  1
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
 29 52  1  6
 30 53  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  C   UNK     0       6.285   2.227  -0.849  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.839   2.444  -1.065  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.968   1.440  -1.144  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.430   0.050  -1.014  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.452  -0.250  -1.918  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.262  -0.911  -1.182  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.717  -0.845  -2.463  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.240  -0.704  -0.146  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.850  -1.656   0.710  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.350  -3.059   0.784  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.828  -1.076   1.581  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.460  -1.518   2.688  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.352   0.111   0.873  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.516   0.470   0.130  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.044   1.229   1.786  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.587   1.676   2.778  0.00  0.00           O+0
HETATM   17  N   UNK     0      -1.293   1.725   1.340  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.009   0.490   0.850  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.272  -0.320   1.854  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.627  -1.617   1.688  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.027   0.964  -0.090  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.537   1.757  -1.028  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.430   0.757  -0.206  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.244   0.260   0.781  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.610   0.023   0.618  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.203   0.294  -0.590  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.436   0.795  -1.615  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.101   1.014  -1.418  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.839  -0.059   0.003  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.065  -1.300  -0.508  0.00  0.00           O+0
HETATM   31  H   UNK     0       6.777   1.730  -1.733  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.505   1.640   0.076  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.772   3.228  -0.783  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.418   3.451  -1.171  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.927   1.646  -1.303  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.840  -0.114   0.002  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.170  -0.777  -1.480  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.717  -1.928  -1.113  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.256  -1.355  -3.120  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.581  -3.713   1.238  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.205  -3.020   1.521  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.744  -3.433  -0.161  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.672   2.692   1.330  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.500  -1.755   1.060  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.905  -2.003   2.735  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.786  -2.304   1.389  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.819   0.061   1.770  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.192  -0.378   1.456  0.00  0.00           H+0
HETATM   49  H   UNK     0      -8.273   0.117  -0.744  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.912   1.012  -2.582  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.492   1.408  -2.228  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.746   0.700  -0.828  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.015  -1.312  -1.503  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5    6   36                                             
CONECT    5    4   37                                                       
CONECT    6    4    7    8   38                                             
CONECT    7    6   39                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   40   41   42                                             
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   29                                             
CONECT   14   13    8                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   43                                                  
CONECT   18   17   19   21   29                                             
CONECT   19   18   20                                                       
CONECT   20   19   44   45   46                                             
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25   47                                                  
CONECT   25   24   26   48                                                  
CONECT   26   25   27   49                                                  
CONECT   27   26   28   50                                                  
CONECT   28   27   23   51                                                  
CONECT   29   18   30   13   52                                             
CONECT   30   29   53                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   17                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   24                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   28                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
    6.2854    2.2270   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    2.4436   -1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    1.4401   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4304    0.0498   -1.0143 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4522   -0.2496   -1.9181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -0.9109   -1.1823 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7171   -0.8450   -2.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -0.7042   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -1.6564    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496   -3.0586    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.0756    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601   -1.5184    2.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518    0.1112    0.8732 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5156    0.4702    0.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439    1.2287    1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868    1.6762    2.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926    1.7248    1.3396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.4898    0.8496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2724   -0.3201    1.8536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -1.6171    1.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.9636   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366    1.7568   -1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4296    0.7569   -0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2443    0.2600    0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6104    0.0227    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028    0.2939   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363    0.7948   -1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009    1.0137   -1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -0.0593    0.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0649   -1.2997   -0.5077 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765    1.7295   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052    1.6402    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7724    3.2276   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185    3.4510   -1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    1.6457   -1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -0.1138    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1704   -0.7769   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172   -1.9283   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565   -1.3547   -3.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -3.7130    1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -3.0204    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -3.4325   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    2.6917    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -1.7550    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9048   -2.0032    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -2.3041    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8191    0.0608    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1923   -0.3779    1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2730    0.1167   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9120    1.0118   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920    1.4078   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    0.7002   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.3120   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 18 29  1  0
 29 30  1  0
 14  8  1  0
 28 23  1  0
 29 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  1
  5 37  1  0
  6 38  1  1
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
 29 52  1  6
 30 53  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃NO₈

Average Mass

417.4140 Da

Monoisotopic Mass

417.14237 Da

IUPAC Name

(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-3-en-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Traditional Name

(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-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

CO[C@]1(NC(=O)[C@]2(OC([C@@H](O)[C@@H](O)\C=C/C)=C(C)C2=O)[C@H]1O)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H23NO8/c1-4-8-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29-3,22-19(20)28)17(26)12-9-6-5-7-10-12/h4-10,13-14,18,23-24,27H,1-3H3,(H,22,28)/b8-4-/t13-,14-,18+,20+,21+/m0/s1

InChI Key

FCGCMRDADMTJIM-LFDIKFNASA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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	NPAtlas	18505285
Aspergillus fumigatus	LOTUS Database	35616633
Cordyceps tenuipes	LOTUS Database	35616633
Isaria tenuipes BCC12625	-	KNApSAcK

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

secondary alcohol (CHEBI:66636 )
alkaloid (CHEBI:66636 )
lactam (CHEBI:66636 )
azaspiro compound (CHEBI:66636 )
oxaspiro compound (CHEBI:66636 )

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	1.26	ALOGPS
logP	0.79	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.8	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	6	ChemAxon
Refractivity	105.8 m³·mol⁻¹	ChemAxon
Polarizability	42.05 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

NPAtlas ID

NPA007733

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23329509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

14-Norpseurotin A

METLIN ID

Not Available

PubChem Compound

24900163

PDB ID

Not Available

ChEBI ID

66636

Good Scents ID

Not Available

References

General References

Zhang M, Wang WL, Fang YC, Zhu TJ, Gu QQ, Zhu WM: Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi. J Nat Prod. 2008 Jun;71(6):985-9. doi: 10.1021/np700737g. Epub 2008 May 28. [PubMed:18505285 ]
Martinez-Luis S, Cherigo L, Arnold E, Spadafora C, Gerwick WH, Cubilla-Rios L: Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544. Nat Prod Commun. 2012 Feb;7(2):165-8. [PubMed:22474943 ]

Showing NP-Card for 14-norpseurotin A (NP0007799)

MOL for NP0007799 (14-norpseurotin A)

3D MOL for NP0007799 (14-norpseurotin A)

3D SDF for NP0007799 (14-norpseurotin A)

3D-SDF for NP0007799 (14-norpseurotin A)

PDB for NP0007799 (14-norpseurotin A)

3D PDB for NP0007799 (14-norpseurotin A)

SMILES for NP0007799 (14-norpseurotin A)

INCHI for NP0007799 (14-norpseurotin A)

Structure for NP0007799 (14-norpseurotin A)

3D Structure for NP0007799 (14-norpseurotin A)