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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:22:41 UTC

Update Date

2022-03-07 02:56:02 UTC

HMDB ID

HMDB0039025

Secondary Accession Numbers

HMDB39025

Metabolite Identification

Common Name

Naphthoherniarin

Description

Naphthoherniarin belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Naphthoherniarin has been detected, but not quantified in, herbs and spices. This could make naphthoherniarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Naphthoherniarin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061310472D          

 28 31  0  0  0  0            999 V2000
    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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
    2.1434    1.2375    0.0000 C   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
    4.2868    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434   -2.8875    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19  9  2  0  0  0  0
 20  5  1  0  0  0  0
 21 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 16  2  0  0  0  0
 24 20  2  0  0  0  0
 25 22  2  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
M  END

HMDB0039025
     RDKit          3D
Naphthoherniarin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.8564   -3.7157   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161   -2.6424   -1.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -1.3808   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1501   -0.6642   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0052    0.6591    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226    1.3787    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.1749    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    2.4494    1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    2.9887    1.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    4.3583    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.2148    1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    0.9290    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1535    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260   -1.0214    0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4482   -1.6219    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -2.8093    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -3.3492    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878   -2.7136    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0294   -3.1872    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5648   -1.5988   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925   -1.0583   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085    0.1146   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918    0.6935   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    1.9018   -1.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774    2.4971   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    0.4087    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7440   -0.8855   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.6251   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8980   -3.5117   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3277   -3.8929    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -4.6294   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.0780   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290    3.0653    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    4.7475    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486    5.0223    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189    4.2586    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    2.6058    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181   -1.4769    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -3.2528    2.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156   -4.2757    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    0.5685   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6256    2.0538   -3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2470    3.5669   -2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    2.5800   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12 26  2  0
 26 27  1  0
 27 28  2  0
 27  3  1  0
 26  7  1  0
 23 13  1  0
 21 15  2  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 22 41  1  0
 25 42  1  0
 25 43  1  0
 25 44  1  0
M  END


  Mrv0541 05061310472D          

 28 31  0  0  0  0            999 V2000
    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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
    2.1434    1.2375    0.0000 C   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
    4.2868    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434   -2.8875    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19  9  2  0  0  0  0
 20  5  1  0  0  0  0
 21 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 16  2  0  0  0  0
 24 20  2  0  0  0  0
 25 22  2  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039025

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)C2=CC(C)=CC(C3=C(OC)C=C4OC(=O)C=CC4=C3)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H16O6/c1-11-6-14(21-15(7-11)16(23)9-19(27-3)22(21)25)13-8-12-4-5-20(24)28-17(12)10-18(13)26-2/h4-10H,1-3H3

> <INCHI_KEY>
MSDIEAZOLJWCBV-UHFFFAOYSA-N

> <FORMULA>
C22H16O6

> <MOLECULAR_WEIGHT>
376.3588

> <EXACT_MASS>
376.094688244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.26329394054886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-8-(7-methoxy-2-oxo-2H-chromen-6-yl)-6-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.9015769436666665

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.115932984654966

> <JCHEM_PKA_STRONGEST_BASIC>
-4.595205733704492

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
105.03299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-8-(7-methoxy-2-oxochromen-6-yl)-6-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039025
     RDKit          3D
Naphthoherniarin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.8564   -3.7157   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161   -2.6424   -1.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -1.3808   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1501   -0.6642   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0052    0.6591    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226    1.3787    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.1749    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    2.4494    1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    2.9887    1.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    4.3583    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.2148    1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    0.9290    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1535    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260   -1.0214    0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4482   -1.6219    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -2.8093    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -3.3492    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878   -2.7136    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0294   -3.1872    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5648   -1.5988   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925   -1.0583   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085    0.1146   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918    0.6935   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    1.9018   -1.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774    2.4971   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    0.4087    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7440   -0.8855   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.6251   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8980   -3.5117   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3277   -3.8929    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -4.6294   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.0780   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290    3.0653    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    4.7475    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486    5.0223    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189    4.2586    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    2.6058    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181   -1.4769    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -3.2528    2.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156   -4.2757    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    0.5685   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6256    2.0538   -3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2470    3.5669   -2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    2.5800   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12 26  2  0
 26 27  1  0
 27 28  2  0
 27  3  1  0
 26  7  1  0
 23 13  1  0
 21 15  2  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 22 41  1  0
 25 42  1  0
 25 43  1  0
 25 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    5   12                                                       
CONECT    5    4   20                                                       
CONECT    6   11   14                                                       
CONECT    7   11   15                                                       
CONECT    8   12   13                                                       
CONECT    9   16   19                                                       
CONECT   10   17   18                                                       
CONECT   11    1    6    7                                                  
CONECT   12    4    8   17                                                  
CONECT   13    8   14   18                                                  
CONECT   14    6   13   21                                                  
CONECT   15    7   16   21                                                  
CONECT   16    9   15   23                                                  
CONECT   17   10   12   28                                                  
CONECT   18   10   13   26                                                  
CONECT   19    9   22   27                                                  
CONECT   20    5   24   28                                                  
CONECT   21   14   15   22                                                  
CONECT   22   19   21   25                                                  
CONECT   23   16                                                            
CONECT   24   20                                                            
CONECT   25   22                                                            
CONECT   26    2   18                                                       
CONECT   27    3   19                                                       
CONECT   28   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0039025
HETATM    1  C1  UNL     1      -3.856  -3.716  -0.578  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.216  -2.642  -1.252  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.095  -1.381  -0.689  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.150  -0.664  -0.434  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.005   0.659   0.158  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.023   1.379   0.416  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.670   1.175   0.463  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.559   2.449   1.000  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.324   2.989   1.281  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.143   4.358   1.856  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.235   2.215   1.008  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.288   0.929   0.469  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.933   0.153   0.298  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.226  -1.021   0.941  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.448  -1.622   0.740  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.784  -2.809   1.368  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.020  -3.349   1.119  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.888  -2.714   0.265  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.029  -3.187   0.019  1.00  0.00           O  
HETATM   20  O4  UNL     1       4.565  -1.599  -0.321  1.00  0.00           O  
HETATM   21  C17 UNL     1       3.392  -1.058  -0.103  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.108   0.115  -0.747  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.892   0.693  -0.535  1.00  0.00           C  
HETATM   24  O5  UNL     1       1.636   1.902  -1.216  1.00  0.00           O  
HETATM   25  C20 UNL     1       2.577   2.497  -2.079  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.531   0.409   0.192  1.00  0.00           C  
HETATM   27  C22 UNL     1      -1.744  -0.886  -0.393  1.00  0.00           C  
HETATM   28  O6  UNL     1      -0.767  -1.625  -0.669  1.00  0.00           O  
HETATM   29  H1  UNL     1      -4.898  -3.512  -0.339  1.00  0.00           H  
HETATM   30  H2  UNL     1      -3.328  -3.893   0.392  1.00  0.00           H  
HETATM   31  H3  UNL     1      -3.794  -4.629  -1.174  1.00  0.00           H  
HETATM   32  H4  UNL     1      -5.132  -1.078  -0.673  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.429   3.065   1.218  1.00  0.00           H  
HETATM   34  H6  UNL     1      -2.063   4.747   2.295  1.00  0.00           H  
HETATM   35  H7  UNL     1      -0.849   5.022   1.017  1.00  0.00           H  
HETATM   36  H8  UNL     1      -0.319   4.259   2.603  1.00  0.00           H  
HETATM   37  H9  UNL     1       0.748   2.606   1.213  1.00  0.00           H  
HETATM   38  H10 UNL     1       0.518  -1.477   1.621  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.061  -3.253   2.019  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.316  -4.276   1.591  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.848   0.569  -1.416  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.626   2.054  -3.080  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.247   3.567  -2.223  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.554   2.580  -1.563  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   32
CONECT    5    6    6    7
CONECT    7    8    8   26
CONECT    8    9   33
CONECT    9   10   11   11
CONECT   10   34   35   36
CONECT   11   12   37
CONECT   12   13   26   26
CONECT   13   14   14   23
CONECT   14   15   38
CONECT   15   16   21   21
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22
CONECT   22   23   23   41
CONECT   23   24
CONECT   24   25
CONECT   25   42   43   44
CONECT   26   27
CONECT   27   28   28
END

HMDB0039025
     RDKit          3D
Naphthoherniarin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.8564   -3.7157   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161   -2.6424   -1.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -1.3808   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1501   -0.6642   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0052    0.6591    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0226    1.3787    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.1749    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    2.4494    1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    2.9887    1.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434    4.3583    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349    2.2148    1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    0.9290    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1535    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260   -1.0214    0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4482   -1.6219    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -2.8093    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -3.3492    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878   -2.7136    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0294   -3.1872    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5648   -1.5988   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925   -1.0583   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085    0.1146   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918    0.6935   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    1.9018   -1.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774    2.4971   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312    0.4087    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7440   -0.8855   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.6251   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8980   -3.5117   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3277   -3.8929    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -4.6294   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1322   -1.0780   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290    3.0653    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    4.7475    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486    5.0223    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189    4.2586    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    2.6058    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5181   -1.4769    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615   -3.2528    2.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156   -4.2757    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8482    0.5685   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6256    2.0538   -3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2470    3.5669   -2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    2.5800   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12 26  2  0
 26 27  1  0
 27 28  2  0
 27  3  1  0
 26  7  1  0
 23 13  1  0
 21 15  2  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 22 41  1  0
 25 42  1  0
 25 43  1  0
 25 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-8-(7-methoxy-2-oxo-2H-1-benzopyran-6-yl)-6-methyl-1,4-naphthalenedione, 9ci	HMDB

Chemical Formula

C₂₂H₁₆O₆

Average Molecular Weight

376.3588

Monoisotopic Molecular Weight

376.094688244

IUPAC Name

2-methoxy-8-(7-methoxy-2-oxo-2H-chromen-6-yl)-6-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

2-methoxy-8-(7-methoxy-2-oxochromen-6-yl)-6-methylnaphthalene-1,4-dione

CAS Registry Number

114032-22-3

SMILES

COC1=CC(=O)C2=CC(C)=CC(C3=C(OC)C=C4OC(=O)C=CC4=C3)=C2C1=O

InChI Identifier

InChI=1S/C22H16O6/c1-11-6-14(21-15(7-11)16(23)9-19(27-3)22(21)25)13-8-12-4-5-20(24)28-17(12)10-18(13)26-2/h4-10H,1-3H3

InChI Key

MSDIEAZOLJWCBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Coumarin
Benzopyran
1-benzopyran
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Pyranone
Pyran
Heteroaromatic compound
Vinylogous ester
Ketone
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039025)

Cellular substructure

Membrane (HMDB: HMDB0039025)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039025)

Source

Exogenous

Food

Food (HMDB: HMDB0039025)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0039025)

Not Available

Nutrient (HMDB: HMDB0039025)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.35 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.9	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.03 m³·mol⁻¹	ChemAxon
Polarizability	38.26 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.685	31661259
DarkChem	[M-H]-	188.644	31661259
DeepCCS	[M+H]+	188.722	30932474
DeepCCS	[M-H]-	186.364	30932474
DeepCCS	[M-2H]-	220.099	30932474
DeepCCS	[M+Na]+	195.327	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.5	32859911
AllCCS	[M+NH4]+	191.4	32859911
AllCCS	[M+Na]+	192.2	32859911
AllCCS	[M-H]-	191.7	32859911
AllCCS	[M+Na-2H]-	191.2	32859911
AllCCS	[M+HCOO]-	190.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naphthoherniarin	COC1=CC(=O)C2=CC(C)=CC(C3=C(OC)C=C4OC(=O)C=CC4=C3)=C2C1=O	4584.6	Standard polar	33892256
Naphthoherniarin	COC1=CC(=O)C2=CC(C)=CC(C3=C(OC)C=C4OC(=O)C=CC4=C3)=C2C1=O	3310.1	Standard non polar	33892256
Naphthoherniarin	COC1=CC(=O)C2=CC(C)=CC(C3=C(OC)C=C4OC(=O)C=CC4=C3)=C2C1=O	3497.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naphthoherniarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-0019000000-07ce89a0f46348b14a8e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naphthoherniarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 10V, Positive-QTOF	splash10-004i-0009000000-fccef834b1e5cb8667a2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 20V, Positive-QTOF	splash10-004i-0029000000-b5b0ae0a2adbbe4bb17d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 40V, Positive-QTOF	splash10-0k9i-6192000000-6e300085ac2cca212331	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 10V, Negative-QTOF	splash10-004i-0009000000-683298b77bc22394ebf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 20V, Negative-QTOF	splash10-004i-0109000000-b5fd42b08a20d41ec6a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 40V, Negative-QTOF	splash10-001i-1937000000-f59d216a21cf386531a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 10V, Negative-QTOF	splash10-004i-0009000000-be4e6c78c9d548edf8b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 20V, Negative-QTOF	splash10-004i-0009000000-fb85da49845511d26d6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 40V, Negative-QTOF	splash10-014j-0029000000-c0d76d8025e3f673cb98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 10V, Positive-QTOF	splash10-004i-0009000000-46102e3cc1dd0b7c44e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 20V, Positive-QTOF	splash10-004i-0009000000-af7251d1dccdc0ff440f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthoherniarin 40V, Positive-QTOF	splash10-014l-1069000000-a4047b6f081e40c3223d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018521

KNApSAcK ID

C00056498

Chemspider ID

322622

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

363452

PDB ID

Not Available

ChEBI ID

169827

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1873641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Naphthoherniarin (HMDB0039025)

MOL for HMDB0039025 (Naphthoherniarin)

3D MOL for HMDB0039025 (Naphthoherniarin)

3D SDF for HMDB0039025 (Naphthoherniarin)

3D-SDF for HMDB0039025 (Naphthoherniarin)

PDB for HMDB0039025 (Naphthoherniarin)

3D PDB for HMDB0039025 (Naphthoherniarin)

SMILES for HMDB0039025 (Naphthoherniarin)

INCHI for HMDB0039025 (Naphthoherniarin)

Structure for HMDB0039025 (Naphthoherniarin)

3D Structure for HMDB0039025 (Naphthoherniarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra