NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione (NP0213104)

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Record Information

Version

2.0

Created at

2022-09-05 11:58:40 UTC

Updated at

2022-09-05 11:58:40 UTC

NP-MRD ID

NP0213104

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione

Description

5,7-Dihydroxy-2-[1-(4-methoxy-6-oxo-6h-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone 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. Based on a literature review very few articles have been published on 5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6h-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213582D          

 32 35  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   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
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -5.9930    2.5864   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055    2.0567   -1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678    1.5993   -0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020    1.0902   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718    0.6358    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186    0.0800    0.2256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5983   -1.3575   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3408   -2.1982    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -2.7712    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -3.5420    2.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -3.7368    2.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4190   -3.1336    1.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990   -2.3588    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1699    0.9304   -0.6542 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534    0.7304   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029    0.2851   -2.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4229    0.0601   -2.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7757   -0.3685   -3.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.3384   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7501    0.1601   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2735   -0.2982   -2.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6335    0.4493   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1830    0.9110    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0521    1.2081    1.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8319    1.0969    1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9614    0.8115   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5122    1.0095    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1511    1.4446    1.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433    0.7179    1.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    1.1932    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527    1.2537    2.8977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    1.6680    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8978    3.6842   -1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6415    2.1238   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5010    2.5439   -2.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804    1.0458   -1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.1352    1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0272   -1.5116   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782   -1.6539   -0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -2.6015    1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153   -3.9880    3.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758   -4.3360    3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4838   -3.2955    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1798   -1.8832   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    1.7259   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003    0.0697   -2.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839   -0.5589   -3.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6933    0.2958   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4483    2.1290    2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    1.4660    1.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5190    2.0576    0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29  5  1  0
  5  4  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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  4  3  1  0
 13  8  1  0
 27 15  1  0
 26 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 32 51  1  0
  4 36  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 16 46  1  0
 21 47  1  0
 22 48  1  0
 24 49  1  0
 25 50  1  0
M  END


  Mrv1652309052213582D          

 32 35  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   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
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0213104

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(=C1)C(CC1=CC=CC=C1)NC1=CC(=O)C2=C(O)C=C(O)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H19NO7/c1-31-15-10-21(32-22(29)11-15)17(7-13-5-3-2-4-6-13)25-18-12-20(28)23-16(24(18)30)8-14(26)9-19(23)27/h2-6,8-12,17,25-27H,7H2,1H3

> <INCHI_KEY>
SDOTUWDXEGNQEU-UHFFFAOYSA-N

> <FORMULA>
C24H19NO7

> <MOLECULAR_WEIGHT>
433.416

> <EXACT_MASS>
433.116151956

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.00697282463656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-{[1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]amino}-1,4-dihydronaphthalene-1,4-dione

> <JCHEM_LOGP>
3.0204066419999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.971396024386667

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.364133963697919

> <JCHEM_PKA_STRONGEST_BASIC>
-4.825064032181144

> <JCHEM_POLAR_SURFACE_AREA>
122.16

> <JCHEM_REFRACTIVITY>
119.42279999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26   15   28                                                  
CONECT   28   27                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₁₉NO₇

Average Mass

433.4160 Da

Monoisotopic Mass

433.11615 Da

IUPAC Name

5,7-dihydroxy-2-{[1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]amino}-1,4-dihydronaphthalene-1,4-dione

Traditional Name

5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(=C1)C(CC1=CC=CC=C1)NC1=CC(=O)C2=C(O)C=C(O)C=C2C1=O

InChI Identifier

InChI=1S/C24H19NO7/c1-31-15-10-21(32-22(29)11-15)17(7-13-5-3-2-4-6-13)25-18-12-20(28)23-16(24(18)30)8-14(26)9-19(23)27/h2-6,8-12,17,25-27H,7H2,1H3

InChI Key

SDOTUWDXEGNQEU-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Naphthoquinone
Amphetamine or derivatives
Naphthalene
Quinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous amide
Vinylogous acid
Ketone
Lactone
Secondary aliphatic amine
Enamine
Ether
Oxacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.02	ChemAxon
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.16 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.42 m³·mol⁻¹	ChemAxon
Polarizability	43.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23076507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132426871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione (NP0213104)

MOL for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

3D MOL for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

3D SDF for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

3D-SDF for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

PDB for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

3D PDB for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

SMILES for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

INCHI for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

Structure for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)

3D Structure for NP0213104 (5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione)