NP-MRD: Showing NP-Card for Pyrophen (NP0010975)

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Record Information

Version

2.0

Created at

2021-01-05 20:45:38 UTC

Updated at

2021-07-15 17:07:37 UTC

NP-MRD ID

NP0010975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrophen

Provided By

NPAtlas

Description

Pyrophen belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Pyrophen is found in Aspergillus niger. Pyrophen was first documented in 1990 (PMID: 2279852). Based on a literature review a small amount of articles have been published on Pyrophen (PMID: 32565683) (PMID: 33375869) (PMID: 32666830) (PMID: 32636705).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107433D          

 38 39  0  0  0  0            999 V2000
   -5.7661   -1.0412    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7497    0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -0.6817   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.3993    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.3390   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.0393   -0.5214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9816   -1.2509   -0.0650 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4066   -0.9041    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.9700   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6362   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218   -0.2309    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0248   -0.1704    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422   -0.5036    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.0578    0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.3078    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.4201    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    2.5011   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5516   -2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.8278   -2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -1.0261   -3.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621   -0.8950   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4412   -0.7345    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.3776   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9020   -2.0721    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.2163    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.3017   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -1.9770   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548   -1.7254    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -1.2814   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -0.6842   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    0.0212    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332    0.1540    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.4413    2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.9302    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.4637    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    3.2848    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.4011    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623   -1.1166   -1.7053 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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21  3  2  0  0  0  0
 13  8  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  6  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 21 38  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7661   -1.0412    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7497    0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -0.6817   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.3993    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.3390   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.0393   -0.5214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9816   -1.2509   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -0.9041    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.9700   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6362   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218   -0.2309    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0248   -0.1704    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422   -0.5036    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.0578    0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.3078    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.4201    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    2.5011   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5516   -2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.8278   -2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -1.0261   -3.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621   -0.8950   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4412   -0.7345    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.3776   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9020   -2.0721    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.2163    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.3017   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -1.9770   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548   -1.7254    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -1.2814   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -0.6842   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    0.0212    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332    0.1540    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.4413    2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.9302    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.4637    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    3.2848    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.4011    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623   -1.1166   -1.7053 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  5 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21  3  2  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 21 38  1  0
M  END


  Mrv1652306242107433D          

 38 39  0  0  0  0            999 V2000
   -5.7661   -1.0412    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7497    0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -0.6817   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.3993    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.3390   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.0393   -0.5214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9816   -1.2509   -0.0650 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4066   -0.9041    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.9700   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6362   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218   -0.2309    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0248   -0.1704    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422   -0.5036    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.0578    0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.3078    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.4201    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    2.5011   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5516   -2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.8278   -2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -1.0261   -3.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621   -0.8950   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4412   -0.7345    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.3776   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9020   -2.0721    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.2163    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.3017   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -1.9770   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548   -1.7254    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -1.2814   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -0.6842   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    0.0212    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332    0.1540    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.4413    2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.9302    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.4637    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    3.2848    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.4011    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623   -1.1166   -1.7053 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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21  3  2  0  0  0  0
 13  8  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  6  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 21 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010975

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c1-11(18)17-14(8-12-6-4-3-5-7-12)15-9-13(20-2)10-16(19)21-15/h3-7,9-10,14H,8H2,1-2H3,(H,17,18)/t14-/m0/s1

> <INCHI_KEY>
VFMQMACUYWGDOJ-AWEZNQCLSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.145943689433956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1S)-1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]acetamide

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.3998652709999992

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.412810149228022

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5418508611821165

> <JCHEM_POLAR_SURFACE_AREA>
64.63

> <JCHEM_REFRACTIVITY>
80.2409

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S)-1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7661   -1.0412    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7497    0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -0.6817   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.3993    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.3390   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.0393   -0.5214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9816   -1.2509   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -0.9041    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.9700   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6362   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218   -0.2309    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0248   -0.1704    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422   -0.5036    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.0578    0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.3078    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.4201    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    2.5011   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5516   -2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.8278   -2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -1.0261   -3.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621   -0.8950   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4412   -0.7345    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.3776   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9020   -2.0721    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.2163    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.3017   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -1.9770   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548   -1.7254    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -1.2814   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -0.6842   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    0.0212    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332    0.1540    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.4413    2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.9302    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.4637    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    3.2848    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.4011    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623   -1.1166   -1.7053 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
  4  5  2  0
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 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 21 38  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      -5.766  -1.041   0.589  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.408  -0.750   0.887  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.442  -0.682  -0.105  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.146  -0.399   0.215  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.204  -0.339  -0.805  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.207  -0.039  -0.521  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.982  -1.251  -0.065  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.407  -0.904   0.212  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.385  -0.970  -0.742  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.684  -0.636  -0.422  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.022  -0.231   0.860  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.025  -0.170   1.807  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.742  -0.504   1.478  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.290   1.058   0.395  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.878   2.308   0.093  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.945   3.420   1.071  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.370   2.501  -1.046  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.577  -0.552  -2.034  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.794  -0.828  -2.431  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.107  -1.026  -3.634  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.762  -0.895  -1.427  0.00  0.00           C+0
HETATM   22  H   UNK     0      -6.441  -0.735   1.397  0.00  0.00           H+0
HETATM   23  H   UNK     0      -6.028  -0.378  -0.288  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.902  -2.072   0.235  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.786  -0.216   1.212  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.688   0.302  -1.464  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.000  -1.977  -0.904  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.555  -1.725   0.830  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.138  -1.281  -1.736  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.474  -0.684  -1.173  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.057   0.021   1.062  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.333   0.154   2.805  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.986  -0.441   2.258  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.109   0.930   1.351  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.002   3.464   1.433  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.284   3.285   1.933  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.781   4.401   0.549  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.762  -1.117  -1.705  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   14   26                                             
CONECT    7    6    8   27   28                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12    8   33                                                  
CONECT   14    6   15   34                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   35   36   37                                             
CONECT   17   15                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   38                                                  
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   21                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7661   -1.0412    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.7497    0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -0.6817   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.3993    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.3390   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.0393   -0.5214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9816   -1.2509   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -0.9041    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.9700   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6362   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218   -0.2309    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0248   -0.1704    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422   -0.5036    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.0578    0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    2.3078    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.4201    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    2.5011   -1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5516   -2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.8278   -2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -1.0261   -3.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621   -0.8950   -1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4412   -0.7345    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.3776   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9020   -2.0721    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.2163    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    0.3017   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -1.9770   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548   -1.7254    0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -1.2814   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -0.6842   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    0.0212    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332    0.1540    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.4413    2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.9302    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.4637    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    3.2848    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.4011    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7623   -1.1166   -1.7053 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
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 15 16  1  0
 15 17  2  0
  5 18  1  0
 18 19  1  0
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 19 21  1  0
 21  3  2  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  9 29  1  0
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 16 35  1  0
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 16 37  1  0
 21 38  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Methoxy-6-(1'-acetamido-2'-phenylethyl)-2H-pyran-2-one	MeSH

Chemical Formula

C₁₆H₁₇NO₄

Average Mass

287.3150 Da

Monoisotopic Mass

287.11576 Da

IUPAC Name

N-[(1S)-1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]acetamide

Traditional Name

N-[(1S)-1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]acetamide

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(=C1)[C@H](CC1=CC=CC=C1)NC(C)=O

InChI Identifier

InChI=1S/C16H17NO4/c1-11(18)17-14(8-12-6-4-3-5-7-12)15-9-13(20-2)10-16(19)21-15/h3-7,9-10,14H,8H2,1-2H3,(H,17,18)/t14-/m0/s1

InChI Key

VFMQMACUYWGDOJ-AWEZNQCLSA-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 niger	NPAtlas	2279852

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Amphetamine or derivatives
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Acetamide
Vinylogous ester
Carboxamide group
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen 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	1.79	ALOGPS
logP	1.4	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.24 m³·mol⁻¹	ChemAxon
Polarizability	30.15 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

NPA006435

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046868

Chemspider ID

116112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131349

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barnes CL, Steiner JR, Torres E, Pacheco R, Marquez H: Structure and absolute configuration of pyrophen, a novel pryrone derivative of L-phenylalanine from Aspergillus niger. Int J Pept Protein Res. 1990 Sep;36(3):292-6. doi: 10.1111/j.1399-3011.1990.tb00981.x. [PubMed:2279852 ]
Ezekiel CN, Kraak B, Sandoval-Denis M, Sulyok M, Oyedele OA, Ayeni KI, Makinde OM, Akinyemi OM, Krska R, Crous PW, Houbraken J: Diversity and toxigenicity of fungi and description of Fusarium madaense sp. nov. from cereals, legumes and soils in north-central Nigeria. MycoKeys. 2020 Jun 8;67:95-124. doi: 10.3897/mycokeys.67.52716. eCollection 2020. [PubMed:32565683 ]
Quang TH, Phong NV, Anh LN, Hanh TTH, Cuong NX, Ngan NTT, Trung NQ, Nam NH, Minh CV: Secondary metabolites from a peanut-associated fungus Aspergillus niger IMBC-NMTP01 with cytotoxic, anti-inflammatory, and antimicrobial activities. Nat Prod Res. 2020 Dec 30:1-9. doi: 10.1080/14786419.2020.1868462. [PubMed:33375869 ]
Han J, Yang N, Wei S, Jia J, Lin R, Li J, Bi H, Song F, Xu X: Dimeric hexylitaconic acids from the marine-derived fungus Aspergillus welwitschiae CUGBMF180262. Nat Prod Res. 2020 Jul 15:1-8. doi: 10.1080/14786419.2020.1793152. [PubMed:32666830 ]
Astuti P, Januarti IB, Kiromah NZW, Fitri HA, Wahyono W, Wahyuono S: Pyrophen Isolated from the Endophytic Fungus Aspergillus fumigatus Strain KARSV04 Synergizes the Effect of Doxorubicin in Killing MCF7 but not T47D Cells. Turk J Pharm Sci. 2020 Jun;17(3):280-284. doi: 10.4274/tjps.galenos.2019.30633. Epub 2020 Jun 22. [PubMed:32636705 ]

Showing NP-Card for Pyrophen (NP0010975)

MOL for NP0010975 (Pyrophen)

3D MOL for NP0010975 (Pyrophen)

3D SDF for NP0010975 (Pyrophen)

3D-SDF for NP0010975 (Pyrophen)

PDB for NP0010975 (Pyrophen)

3D PDB for NP0010975 (Pyrophen)

SMILES for NP0010975 (Pyrophen)

INCHI for NP0010975 (Pyrophen)

Structure for NP0010975 (Pyrophen)

3D Structure for NP0010975 (Pyrophen)