NP-MRD: Showing NP-Card for Aureusamine A (NP0009261)

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Record Information

Version

2.0

Created at

2020-12-09 06:40:09 UTC

Updated at

2021-07-15 17:02:45 UTC

NP-MRD ID

NP0009261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aureusamine A

Provided By

NPAtlas

Description

Tyrvalin, also known as aureusamine a, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Tyrvalin 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. Aureusamine A is found in Staphylococcus aureus. Aureusamine A was first documented in 2012 (PMID: 22808288). Based on a literature review very few articles have been published on tyrvalin (PMID: 23070851).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106343D          

 34 35  0  0  0  0            999 V2000
   -4.6104    0.1797   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9346    0.6175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6179    0.1606    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819    0.9379    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.2048   -1.0228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.2046   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.9411   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    0.9299   -1.5275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5308   -0.0915   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.2649    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6602    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.9486    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972   -2.9072    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4156   -2.3088   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.3728   -1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.6755    0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.6789    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    2.3665    1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -0.8002   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.0222    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531    0.8323   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    1.9561    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.9290    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    0.3495    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    0.5081    2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -0.3867   -2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.9356   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683    0.7355   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.2671    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -0.3622    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -3.5034    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -3.3338   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -1.7179   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.2366    0.5604 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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17  4  1  0  0  0  0
 15  9  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  6 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
M  END

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6104    0.1797   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9346    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    0.1606    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819    0.9379    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.2048   -1.0228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.2046   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.9411   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    0.9299   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308   -0.0915   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.2649    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6602    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.9486    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972   -2.9072    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4156   -2.3088   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.3728   -1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.6755    0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.6789    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    2.3665    1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -0.8002   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.0222    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531    0.8323   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    1.9561    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.9290    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    0.3495    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    0.5081    2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -0.3867   -2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.9356   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683    0.7355   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.2671    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -0.3622    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -3.5034    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -3.3338   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -1.7179   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.2366    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv1652306242106343D          

 34 35  0  0  0  0            999 V2000
   -4.6104    0.1797   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9346    0.6175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6179    0.1606    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819    0.9379    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.2048   -1.0228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.2046   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.9411   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    0.9299   -1.5275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5308   -0.0915   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.2649    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6602    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.9486    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972   -2.9072    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4156   -2.3088   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.3728   -1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.6755    0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.6789    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    2.3665    1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -0.8002   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.0222    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531    0.8323   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    1.9561    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.9290    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    0.3495    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    0.5081    2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -0.3867   -2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.9356   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683    0.7355   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.2671    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -0.3622    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -3.5034    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -3.3338   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -1.7179   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.2366    0.5604 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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17  4  1  0  0  0  0
 15  9  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  6 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C1=C([H])N=C(C(=O)N1[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O2/c1-9(2)13-14(18)16-11(8-15-13)7-10-3-5-12(17)6-4-10/h3-6,8-9,17H,7H2,1-2H3,(H,16,18)

> <INCHI_KEY>
OVNQNQOVBVQZCE-UHFFFAOYSA-N

> <FORMULA>
C14H16N2O2

> <MOLECULAR_WEIGHT>
244.294

> <EXACT_MASS>
244.121177763

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.380932063531596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(4-hydroxyphenyl)methyl]-3-(propan-2-yl)-1,2-dihydropyrazin-2-one

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.4718740823333336

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.05410543304774

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.48779546839093

> <JCHEM_PKA_STRONGEST_BASIC>
0.10015727519625117

> <JCHEM_POLAR_SURFACE_AREA>
61.690000000000005

> <JCHEM_REFRACTIVITY>
70.6914

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(4-hydroxyphenyl)methyl]-3-isopropyl-1H-pyrazin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6104    0.1797   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9346    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    0.1606    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819    0.9379    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.2048   -1.0228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.2046   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.9411   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    0.9299   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308   -0.0915   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.2649    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6602    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.9486    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972   -2.9072    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4156   -2.3088   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.3728   -1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.6755    0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.6789    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    2.3665    1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -0.8002   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.0222    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531    0.8323   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    1.9561    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.9290    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    0.3495    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    0.5081    2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -0.3867   -2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.9356   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683    0.7355   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.2671    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -0.3622    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -3.5034    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -3.3338   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -1.7179   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.2366    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  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      -4.610   0.180  -0.316  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.672   0.935   0.618  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.618   0.161   1.917  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.282   0.938   0.060  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.975   0.205  -1.023  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.725   0.205  -1.521  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.297   0.941  -0.963  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.673   0.930  -1.528  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.531  -0.092  -0.902  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.289   0.265   0.189  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.118  -0.660   0.815  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.185  -1.949   0.343  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.997  -2.907   0.934  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.416  -2.309  -0.763  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.587  -1.373  -1.385  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.009   1.676   0.121  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.273   1.679   0.629  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.553   2.366   1.642  0.00  0.00           O+0
HETATM   19  H   UNK     0      -4.227  -0.800  -0.610  0.00  0.00           H+0
HETATM   20  H   UNK     0      -5.549   0.022   0.253  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.853   0.832  -1.182  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.030   1.956   0.720  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.760  -0.929   1.758  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.719   0.350   2.510  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.497   0.508   2.523  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.462  -0.387  -2.400  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.154   1.936  -1.435  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.668   0.736  -2.627  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.291   1.267   0.622  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.703  -0.362   1.666  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.651  -3.503   1.688  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.498  -3.334  -1.100  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.018  -1.718  -2.235  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.735   2.237   0.560  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3    4   22                                             
CONECT    3    2   23   24   25                                             
CONECT    4    2    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   27   28                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   31                                                       
CONECT   14   12   15   32                                                  
CONECT   15   14    9   33                                                  
CONECT   16    7   17   34                                                  
CONECT   17   16   18    4                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    6                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

RDKit          3D

34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6104    0.1797   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9346    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    0.1606    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819    0.9379    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.2048   -1.0228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.2046   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.9411   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    0.9299   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308   -0.0915   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.2649    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6602    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.9486    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972   -2.9072    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4156   -2.3088   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.3728   -1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.6755    0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    1.6789    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    2.3665    1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -0.8002   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.0222    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531    0.8323   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    1.9561    0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.9290    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    0.3495    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    0.5081    2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -0.3867   -2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.9356   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683    0.7355   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914    1.2671    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -0.3622    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -3.5034    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -3.3338   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -1.7179   -2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.2366    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-(4-Hydroxybenzyl)-3-isopropylpyrazin-2(1H)-one	ChEBI
6-[(4-Hydroxyphenyl)methyl]-3-(1-methylethyl)-2(1H)-pyrazinone	ChEBI
6-[(4-Hydroxyphenyl)methyl]-3-(propan-2-yl)-1,2-dihydropyrazin-2-one	ChEBI
6-[(4-Hydroxyphenyl)methyl]-3-(propan-2-yl)pyrazin-2(1H)-one	ChEBI
6-[(4-Hydroxyphenyl)methyl]-3-isopropyl-1H-pyrazin-2-one	ChEBI
Aureusamine a	ChEBI
Aureusimine a	ChEBI

Chemical Formula

C₁₄H₁₆N₂O₂

Average Mass

244.2940 Da

Monoisotopic Mass

244.12118 Da

IUPAC Name

6-[(4-hydroxyphenyl)methyl]-3-(propan-2-yl)-1,2-dihydropyrazin-2-one

Traditional Name

6-[(4-hydroxyphenyl)methyl]-3-isopropyl-1H-pyrazin-2-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=NC=C(CC2=CC=C(O)C=C2)NC1=O

InChI Identifier

InChI=1S/C14H16N2O2/c1-9(2)13-14(18)16-11(8-15-13)7-10-3-5-12(17)6-4-10/h3-6,8-9,17H,7H2,1-2H3,(H,16,18)

InChI Key

OVNQNQOVBVQZCE-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
Staphylococcus aureus	NPAtlas	20522739

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Pyrazine
Monocyclic benzene moiety
Heteroaromatic compound
Lactam
Azacycle
Organoheterocyclic compound
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	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.31	ALOGPS
logP	2.47	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	0.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.69 m³·mol⁻¹	ChemAxon
Polarizability	26.38 Å³	ChemAxon
Number of Rings	2	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

NPA020443

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

48059648

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49838500

PDB ID

Not Available

ChEBI ID

167319

Good Scents ID

Not Available

References

General References

Secor PR, Jennings LK, James GA, Kirker KR, Pulcini ED, McInnerney K, Gerlach R, Livinghouse T, Hilmer JK, Bothner B, Fleckman P, Olerud JE, Stewart PS: Phevalin (aureusimine B) production by Staphylococcus aureus biofilm and impacts on human keratinocyte gene expression. PLoS One. 2012;7(7):e40973. doi: 10.1371/journal.pone.0040973. Epub 2012 Jul 13. [PubMed:22808288 ]
Wyatt MA, Mok MC, Junop M, Magarvey NA: Heterologous expression and structural characterisation of a pyrazinone natural product assembly line. Chembiochem. 2012 Nov 5;13(16):2408-15. doi: 10.1002/cbic.201200340. Epub 2012 Oct 15. [PubMed:23070851 ]

Showing NP-Card for Aureusamine A (NP0009261)

MOL for NP0009261 (Aureusamine A)

3D MOL for NP0009261 (Aureusamine A)

3D SDF for NP0009261 (Aureusamine A)

3D-SDF for NP0009261 (Aureusamine A)

PDB for NP0009261 (Aureusamine A)

3D PDB for NP0009261 (Aureusamine A)

SMILES for NP0009261 (Aureusamine A)

INCHI for NP0009261 (Aureusamine A)

Structure for NP0009261 (Aureusamine A)

3D Structure for NP0009261 (Aureusamine A)