NP-MRD: Showing NP-Card for (2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione (NP0307438)

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Record Information

Version

2.0

Created at

2022-09-11 00:33:42 UTC

Updated at

2022-09-11 00:33:42 UTC

NP-MRD ID

NP0307438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione

Description

Erythrostominone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. (2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione is found in Ophiocordyceps unilateralis. (2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione was first documented in 2015 (PMID: 26193948). Based on a literature review a small amount of articles have been published on Erythrostominone (PMID: 31344623) (PMID: 29291525) (PMID: 28891787) (PMID: 28340455).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202332D          

 25 27  0  0  1  0            999 V2000
   -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 O   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 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 O   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 O   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   -1.6500    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    6.4606    1.3759    1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570    1.6717    1.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0912    0.9963    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381    0.0378    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2391   -0.7076   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054   -1.6197   -1.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.4009   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784   -1.1639   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -2.1240   -1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -0.8889   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.1075    0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    0.8618    1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1151    1.8268    1.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029    0.5920    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    1.3279    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    2.2391    2.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499    0.3783    0.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -0.6876    0.7155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4004   -0.1745    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957    0.6139   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.0485   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3027    0.1162   -1.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627   -1.6956   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -1.6501   -1.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1453   -2.9606   -1.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542    1.5476    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7458    0.3171    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1426    2.0318    1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3624   -0.2411   -0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8478   -2.7700   -2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    2.4263    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424   -1.1644    1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0700   -1.0593    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6079    0.4077    1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039    2.0923   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328    2.7116   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    2.4055    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -1.7104   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156   -2.7350    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -1.1491   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271   -3.2309   -2.3775 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
  8 10  1  0
 10 11  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
 14  7  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  9 30  1  0
 18 32  1  1
 19 33  1  0
 19 34  1  0
 21 35  1  0
 21 36  1  0
 21 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  6
 25 41  1  0
 13 31  1  0
M  END


  Mrv1652309112202332D          

 25 27  0  0  1  0            999 V2000
   -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 O   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 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 O   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 O   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   -1.6500    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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   -2.8875    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0307438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C3=C(O[C@@H](CC(C)=O)C[C@@H]3O)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O8/c1-6(18)3-7-4-8(19)12-15(22)11-9(20)5-10(24-2)14(21)13(11)16(23)17(12)25-7/h5,7-8,19,22-23H,3-4H2,1-2H3/t7-,8-/m0/s1

> <INCHI_KEY>
XCCPWOLOVUKRKJ-YUMQZZPRSA-N

> <FORMULA>
C17H16O8

> <MOLECULAR_WEIGHT>
348.307

> <EXACT_MASS>
348.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.57416435186123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4S)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2H,3H,4H,6H,9H-naphtho[2,3-b]pyran-6,9-dione

> <JCHEM_LOGP>
0.9089264853333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.48941853819423

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.742555853244829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.387038512471542

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
86.7146

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2H,3H,4H-naphtho[2,3-b]pyran-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   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  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+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  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   10   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₈

Average Mass

348.3070 Da

Monoisotopic Mass

348.08452 Da

IUPAC Name

(2R,4S)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2H,3H,4H,6H,9H-naphtho[2,3-b]pyran-6,9-dione

Traditional Name

(2R,4S)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2H,3H,4H-naphtho[2,3-b]pyran-6,9-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C3=C(O[C@@H](CC(C)=O)C[C@@H]3O)C(O)=C2C1=O

InChI Identifier

InChI=1S/C17H16O8/c1-6(18)3-7-4-8(19)12-15(22)11-9(20)5-10(24-2)14(21)13(11)16(23)17(12)25-7/h5,7-8,19,22-23H,3-4H2,1-2H3/t7-,8-/m0/s1

InChI Key

XCCPWOLOVUKRKJ-YUMQZZPRSA-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

Species Name	Source	Reference
Ophiocordyceps unilateralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Chromane
Benzopyran
Naphthalene
1-benzopyran
Quinone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Vinylogous acid
Vinylogous ester
Ketone
Secondary alcohol
Polyol
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen 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	0.91	ChemAxon
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.71 m³·mol⁻¹	ChemAxon
Polarizability	33.57 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038279

Chemspider ID

156223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

179473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abe FR, Machado AL, Soares AMVM, Oliveira DP, Pestana JLT: Life history and behavior effects of synthetic and natural dyes on Daphnia magna. Chemosphere. 2019 Dec;236:124390. doi: 10.1016/j.chemosphere.2019.124390. Epub 2019 Jul 17. [PubMed:31344623 ]
Abe FR, Soares AMVM, Oliveira DP, Gravato C: Toxicity of dyes to zebrafish at the biochemical level: Cellular energy allocation and neurotoxicity. Environ Pollut. 2018 Apr;235:255-262. doi: 10.1016/j.envpol.2017.12.020. Epub 2018 Jan 4. [PubMed:29291525 ]
Abe FR, Gravato C, Soares AMVM, de Oliveira DP: Biochemical approaches to assess oxidative stress induced by exposure to natural and synthetic dyes in early life stages in zebrafish. J Toxicol Environ Health A. 2017;80(23-24):1259-1268. doi: 10.1080/15287394.2017.1371091. Epub 2017 Sep 11. [PubMed:28891787 ]
Abe FR, Mendonca JN, Moraes LA, Oliveira GA, Gravato C, Soares AM, Oliveira DP: Toxicological and behavioral responses as a tool to assess the effects of natural and synthetic dyes on zebrafish early life. Chemosphere. 2017 Jul;178:282-290. doi: 10.1016/j.chemosphere.2017.03.030. Epub 2017 Mar 9. [PubMed:28340455 ]
Khaokhajorn P, Samipak S, Nithithanasilp S, Tanticharoen M, Amnuaykanjanasin A: Production and secretion of naphthoquinones is mediated by the MFS transporter MFS1 in the entomopathogenic fungus Ophiocordyceps sp. BCC1869. World J Microbiol Biotechnol. 2015 Oct;31(10):1543-54. doi: 10.1007/s11274-015-1903-5. Epub 2015 Jul 21. [PubMed:26193948 ]
LOTUS database [Link]

Showing NP-Card for (2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione (NP0307438)

MOL for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

3D MOL for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

3D SDF for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

3D-SDF for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

PDB for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

3D PDB for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

SMILES for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

INCHI for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

Structure for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)

3D Structure for NP0307438 ((2r,4s)-4,5,10-trihydroxy-8-methoxy-2-(2-oxopropyl)-2h,3h,4h-naphtho[2,3-b]pyran-6,9-dione)