NP-MRD: Showing NP-Card for (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0151676)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 08:01:35 UTC

Updated at

2022-09-02 08:01:35 UTC

NP-MRD ID

NP0151676

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]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

Description

Pseurotin F2 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. (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one is found in Aspergillus fumigatus. (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one was first documented in 2017 (PMID: 28213885). Based on a literature review very few articles have been published on pseurotin F2.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210012D          

 30 32  0  0  1  0            999 V2000
   -0.3225   -3.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587   -2.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2486   -1.7903    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
   -1.4211   -0.1494    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
    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  6  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
 19 21  1  1  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
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    5.0294    3.1788    0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    2.3819   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    2.1364    0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4025    0.9298    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830   -0.2473    0.2929 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9164   -0.3781   -1.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7329   -1.5271    1.0125 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5573   -2.5191    0.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -1.8696    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8409   -2.9842    0.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -4.0880   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6257   -2.9794    0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.9395    0.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -1.5697    0.7736 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2348   -1.0839    1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106   -1.4827    1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272   -1.6474    3.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1732   -1.2212    0.9818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8796   -1.1049   -0.4223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0934   -2.3549   -1.0667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151   -0.1232   -1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293   -0.4530   -2.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    1.2575   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    1.7894    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    3.1321    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1187    3.9981    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    3.4541   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281    2.1359   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761   -0.8304   -0.4655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8540   -1.5297   -1.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6563    3.5845    1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9184    2.5583    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3783    4.0415   -0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    2.9805   -1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.4538   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815    2.9847    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    0.8248    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -0.0994    0.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -1.1516   -1.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882   -1.3569    2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1566   -2.9132    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367   -3.7153   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059   -4.8445   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -4.6095    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -1.0277    3.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0332   -2.5045   -1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215    1.1658    1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7916    3.5316    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2271    5.0368    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4137    4.0821   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    1.7379   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167    0.2164   -0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2289   -2.4371   -1.6351 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 29  1  0
 29 30  1  0
 29 19  1  0
 19 20  1  6
 19 18  1  0
 18 16  2  0
 16 17  1  0
 19 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
 15  9  1  0
 28 23  1  0
 16 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  7 40  1  1
  8 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
 29 52  1  1
 30 53  1  0
 20 46  1  0
 17 45  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
M  END


  Mrv1652309022210012D          

 30 32  0  0  1  0            999 V2000
   -0.3225   -3.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587   -2.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2486   -1.7903    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
   -1.4211   -0.1494    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
    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  6  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
 19 21  1  1  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
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0151676

> <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@@](O)(N=C2O)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO8/c1-3-4-10-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29,22-19(20)28)17(26)12-8-6-5-7-9-12/h4-10,13-14,18,23-24,27,29H,3H2,1-2H3,(H,22,28)/b10-4-/t13-,14-,18+,20+,21+/m0/s1

> <INCHI_KEY>
BCXXBFMWUYYHIF-BJBAUCALSA-N

> <FORMULA>
C21H23NO8

> <MOLECULAR_WEIGHT>
417.414

> <EXACT_MASS>
417.142366705

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.35973584098464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <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]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
1.410619744

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.10013432309599

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4241842557748328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3677757468869975

> <JCHEM_POLAR_SURFACE_AREA>
156.88

> <JCHEM_REFRACTIVITY>
106.17040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.602  -7.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.763  -5.500   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.483  -4.595   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.322  -3.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.085  -2.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.331  -3.342   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      -2.653  -0.279   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       5.060  -1.506   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.915  -2.537   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.524  -1.982   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.669  -0.952   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.134  -1.428   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.454  -2.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.309  -3.964   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.845  -3.489   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   30  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   29                                             
CONECT   15   14    9                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   29                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   19   14   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃NO₈

Average Mass

417.4140 Da

Monoisotopic Mass

417.14237 Da

IUPAC Name

(5R,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-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]-6,8,9-trihydroxy-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@@](O)(N=C2O)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H23NO8/c1-3-4-10-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29,22-19(20)28)17(26)12-8-6-5-7-9-12/h4-10,13-14,18,23-24,27,29H,3H2,1-2H3,(H,22,28)/b10-4-/t13-,14-,18+,20+,21+/m0/s1

InChI Key

BCXXBFMWUYYHIF-BJBAUCALSA-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

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
Benzenoid
2-pyrrolidone
Alpha-hydroxy ketone
Dihydrofuran
Pyrrolidine
Vinylogous ester
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Alkanolamine
Organonitrogen compound
Aldehyde
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic nitrogen 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	0.49	ALOGPS
logP	1.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.88 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.17 m³·mol⁻¹	ChemAxon
Polarizability	41.36 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

9514000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11339056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Magotra A, Kumar M, Kushwaha M, Awasthi P, Raina C, Gupta AP, Shah BA, Gandhi SG, Chaubey A: Epigenetic modifier induced enhancement of fumiquinazoline C production in Aspergillus fumigatus (GA-L7): an endophytic fungus from Grewia asiatica L. AMB Express. 2017 Dec;7(1):43. doi: 10.1186/s13568-017-0343-z. Epub 2017 Feb 17. [PubMed:28213885 ]
LOTUS database [Link]

Showing NP-Card for (5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0151676)

MOL for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D MOL for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D SDF for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D-SDF for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

PDB for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D PDB for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

SMILES for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

INCHI for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

Structure for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D Structure for NP0151676 ((5r,8s,9r)-8-benzoyl-2-[(1s,2s,3z)-1,2-dihydroxyhex-3-en-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)