NP-MRD: Showing NP-Card for Aspergillic acid (NP0004775)

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Record Information

Version

2.0

Created at

2020-12-09 02:11:35 UTC

Updated at

2021-08-19 23:59:36 UTC

NP-MRD ID

NP0004775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergillic acid

Provided By

NPAtlas

Description

Aspergillic acid is found in Aspergillus flavus. Aspergillic acid was first documented in 1958 (PMID: 13549463). Based on a literature review very few articles have been published on 6-(butan-2-yl)-1-hydroxy-3-(2-methylpropyl)-1,2-dihydropyrazin-2-one (PMID: 32403244) (PMID: 30513994) (PMID: 29885975) (PMID: 29674152).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 36 36  0  0  0  0            999 V2000
   -4.6030    0.3061    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.5651    1.2877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7895   -0.2651    0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6455    0.0773   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -0.1201   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    1.1329   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.2777   -0.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    0.2102   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3890   -1.0790 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6291    0.5090    0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0627    0.6879   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.6139    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.0170   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -2.0378   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.1975   -0.1845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.4547    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    0.4356    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    1.0510    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.7077    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.2387    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    1.6616    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -1.3228    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278    0.6913   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.8506   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    0.5870   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623    1.9836   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.3163   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4260   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    1.4846    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467    0.3911    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2360    1.7383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793    0.0686   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -0.3900    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5802    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.6878    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -3.1318   -0.6412 H   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  5  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  1  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 16 36  1  0  0  0  0
M  END

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6030    0.3061    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.5651    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -0.2651    0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6455    0.0773   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -0.1201   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    1.1329   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.2777   -0.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    0.2102   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3890   -1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    0.5090    0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0627    0.6879   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.6139    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.0170   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -2.0378   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.1975   -0.1845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.4547    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    0.4356    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    1.0510    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.7077    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.2387    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    1.6616    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -1.3228    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278    0.6913   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.8506   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    0.5870   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623    1.9836   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.3163   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4260   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    1.4846    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467    0.3911    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2360    1.7383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793    0.0686   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -0.3900    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5802    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.6878    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -3.1318   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  1
  4 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
M  END


  Mrv1652306242121113D          

 36 36  0  0  0  0            999 V2000
   -4.6030    0.3061    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.5651    1.2877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7895   -0.2651    0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6455    0.0773   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -0.1201   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    1.1329   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.2777   -0.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    0.2102   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3890   -1.0790 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6291    0.5090    0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0627    0.6879   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.6139    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.0170   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -2.0378   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.1975   -0.1845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.4547    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    0.4356    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    1.0510    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.7077    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.2387    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    1.6616    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -1.3228    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278    0.6913   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.8506   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    0.5870   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623    1.9836   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.3163   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4260   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    1.4846    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467    0.3911    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2360    1.7383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793    0.0686   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -0.3900    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5802    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.6878    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -3.1318   -0.6412 H   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  5  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  1  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 16 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON1C(=O)C(=NC([H])=C1[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N2O2/c1-5-9(4)11-7-13-10(6-8(2)3)12(15)14(11)16/h7-9,16H,5-6H2,1-4H3/t9-/m1/s1

> <INCHI_KEY>
IUZCDJYHMMWBBE-UHFFFAOYSA-N

> <FORMULA>
C12H20N2O2

> <MOLECULAR_WEIGHT>
224.304

> <EXACT_MASS>
224.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.484966224447053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2R)-butan-2-yl]-1-hydroxy-3-(2-methylpropyl)-1,2-dihydropyrazin-2-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.6365966783333326

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.040679935396287

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569228356918699

> <JCHEM_POLAR_SURFACE_AREA>
52.900000000000006

> <JCHEM_REFRACTIVITY>
64.02780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2R)-butan-2-yl]-1-hydroxy-3-(2-methylpropyl)pyrazin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6030    0.3061    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.5651    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -0.2651    0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6455    0.0773   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -0.1201   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    1.1329   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.2777   -0.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    0.2102   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3890   -1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    0.5090    0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0627    0.6879   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.6139    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.0170   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -2.0378   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.1975   -0.1845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.4547    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    0.4356    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    1.0510    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.7077    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.2387    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    1.6616    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -1.3228    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278    0.6913   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.8506   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    0.5870   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623    1.9836   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.3163   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4260   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    1.4846    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467    0.3911    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2360    1.7383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793    0.0686   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -0.3900    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5802    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.6878    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -3.1318   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  1
  4 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  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      -4.603   0.306   1.644  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.150   0.565   1.288  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.789  -0.265   0.073  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.646   0.077  -1.126  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.341  -0.120  -0.231  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.867   1.133  -0.553  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.437   1.278  -0.829  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.296   0.210  -0.795  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.734   0.389  -1.079  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.629   0.509   0.090  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.063   0.688  -0.423  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.654  -0.614   1.061  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.785  -1.017  -0.471  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.509  -2.038  -0.425  0.00  0.00           O+0
HETATM   15  N   UNK     0      -0.540  -1.198  -0.185  0.00  0.00           N+0
HETATM   16  O   UNK     0      -0.994  -2.455   0.135  0.00  0.00           O+0
HETATM   17  H   UNK     0      -4.751   0.436   2.748  0.00  0.00           H+0
HETATM   18  H   UNK     0      -5.212   1.051   1.092  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.939  -0.708   1.323  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.473   0.239   2.103  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.033   1.662   1.074  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.016  -1.323   0.325  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.528   0.691  -0.863  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.049  -0.851  -1.625  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.056   0.587  -1.919  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.562   1.984  -0.578  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.808   1.316  -1.722  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.080  -0.426  -1.781  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.383   1.485   0.599  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.747   0.391   0.373  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.236   1.738  -0.703  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.179   0.069  -1.343  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.389  -0.390   1.906  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.940  -1.580   0.649  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.681  -0.688   1.594  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.001  -3.132  -0.641  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3   20   21                                             
CONECT    3    2    4    5   22                                             
CONECT    4    3   23   24   25                                             
CONECT    5    3    6   15                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   27   28                                             
CONECT   10    9   11   12   29                                             
CONECT   11   10   30   31   32                                             
CONECT   12   10   33   34   35                                             
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16    5                                                  
CONECT   16   15   36                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    2                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   16                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

RDKit          3D

36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6030    0.3061    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.5651    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -0.2651    0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6455    0.0773   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -0.1201   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    1.1329   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.2777   -0.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    0.2102   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3890   -1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    0.5090    0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0627    0.6879   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.6139    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.0170   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -2.0378   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.1975   -0.1845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.4547    0.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    0.4356    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    1.0510    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.7077    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.2387    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    1.6616    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -1.3228    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278    0.6913   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.8506   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    0.5870   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623    1.9836   -0.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.3163   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4260   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    1.4846    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467    0.3911    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2360    1.7383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793    0.0686   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893   -0.3900    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5802    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.6878    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -3.1318   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  1
  4 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-Sec-butyl-1-hydroxy-3-isobutyl-2(1H)-pyrazinone	MeSH
ASPERGILLate	Generator

Chemical Formula

C₁₂H₂₀N₂O₂

Average Mass

224.3040 Da

Monoisotopic Mass

224.15248 Da

IUPAC Name

6-[(2R)-butan-2-yl]-1-hydroxy-3-(2-methylpropyl)-1,2-dihydropyrazin-2-one

Traditional Name

6-[(2R)-butan-2-yl]-1-hydroxy-3-(2-methylpropyl)pyrazin-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)C1=CN=C(CC(C)C)C(=O)N1O

InChI Identifier

InChI=1S/C12H20N2O2/c1-5-9(4)11-7-13-10(6-8(2)3)12(15)14(11)16/h7-9,16H,5-6H2,1-4H3

InChI Key

IUZCDJYHMMWBBE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus flavus	NPAtlas	13549463

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	98.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	336.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	929.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.810 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.3	ALOGPS
logP	2.64	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.04	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.03 m³·mol⁻¹	ChemAxon
Polarizability	25.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA028490

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002316

Chemspider ID

9853

KEGG Compound ID

C10571

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10272

PDB ID

Not Available

ChEBI ID

2879

Good Scents ID

rw1464041

References

General References

DUTCHER JD: Aspergillic acid; an antibiotic substance produced by Aspergillus flavus. J Biol Chem. 1958 Jun;232(2):785-95. [PubMed:13549463 ]
Francis F, Druart F, Mavungu JDD, De Boevre M, De Saeger S, Delvigne F: Biofilm Mode of Cultivation Leads to an Improvement of the Entomotoxic Patterns of Two Aspergillus Species. Microorganisms. 2020 May 11;8(5). pii: microorganisms8050705. doi: 10.3390/microorganisms8050705. [PubMed:32403244 ]
Singh P, Orbach MJ, Cotty PJ: Aspergillus texensis: A Novel Aflatoxin Producer with S Morphology from the United States. Toxins (Basel). 2018 Dec 3;10(12). pii: toxins10120513. doi: 10.3390/toxins10120513. [PubMed:30513994 ]
Norlia M, Jinap S, Nor-Khaizura MAR, Son R, Chin CK, Sardjono: Polyphasic approach to the identification and characterization of aflatoxigenic strains of Aspergillus section Flavi isolated from peanuts and peanut-based products marketed in Malaysia. Int J Food Microbiol. 2018 Oct 3;282:9-15. doi: 10.1016/j.ijfoodmicro.2018.05.030. Epub 2018 May 31. [PubMed:29885975 ]
Lebar MD, Cary JW, Majumdar R, Carter-Wientjes CH, Mack BM, Wei Q, Uka V, De Saeger S, Diana Di Mavungu J: Identification and functional analysis of the aspergillic acid gene cluster in Aspergillus flavus. Fungal Genet Biol. 2018 Jul;116:14-23. doi: 10.1016/j.fgb.2018.04.009. Epub 2018 Apr 16. [PubMed:29674152 ]

Showing NP-Card for Aspergillic acid (NP0004775)

MOL for NP0004775 (Aspergillic acid)

3D MOL for NP0004775 (Aspergillic acid)

3D SDF for NP0004775 (Aspergillic acid)

3D-SDF for NP0004775 (Aspergillic acid)

PDB for NP0004775 (Aspergillic acid)

3D PDB for NP0004775 (Aspergillic acid)

SMILES for NP0004775 (Aspergillic acid)

INCHI for NP0004775 (Aspergillic acid)

Structure for NP0004775 (Aspergillic acid)

3D Structure for NP0004775 (Aspergillic acid)