NP-MRD: Showing NP-Card for 3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one (NP0180606)

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Record Information

Version

2.0

Created at

2022-09-03 18:59:37 UTC

Updated at

2022-09-03 18:59:37 UTC

NP-MRD ID

NP0180606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one

Description

Hypoxylonol A belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. 3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one is found in Annulohypoxylon truncatum. 3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one was first documented in 2014 (PMID: 24934680). Based on a literature review very few articles have been published on Hypoxylonol A (PMID: 34782905).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220592D          

 27 31  0  0  0  0            999 V2000
   -0.2878    3.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    3.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239    3.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357    3.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1778    2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9475    2.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0502    1.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945    1.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8426    1.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6665    1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0424    1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5944    0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9703   -0.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7704    0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -0.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983   -0.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984    0.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    1.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385    2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2806    1.5639    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  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  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
  8 27  1  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
    6.0917    0.3164    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6079    0.5012    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633   -0.2086   -0.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -0.0334   -0.1411 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9232   -1.3099    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6290   -0.8768    1.1560 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2489   -1.9644    1.8487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3102   -0.3959    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -0.3571   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7011   -0.8355    0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504   -2.0118    1.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455   -2.3722    2.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8459   -1.5225    2.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8955   -0.3094    1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    0.4773    1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104    0.0231    0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    1.2589    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665    2.2375    0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937    1.4578   -1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9472    0.3157   -1.3806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6344    0.6807   -1.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    1.3271   -3.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397    1.5163   -3.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1107    1.0799   -2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224    1.2979   -2.6060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744    0.4470   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3123    0.2697   -1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4034   -0.6990    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6017    1.0310    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4082    0.5825   -0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580    0.1063    1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677    1.5821    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.6970    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6597   -1.9550   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666   -1.8071    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -0.0336    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0192   -2.3391    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616   -2.6806    1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186   -3.3098    2.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6556   -1.8620    2.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2354    1.3481    1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    2.3803   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992    1.5995   -1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4229   -0.3882   -2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9608    1.6539   -3.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5006    2.0233   -4.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935    1.0615   -2.0838 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  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26  4  1  0
 27  8  1  0
 10  9  1  0
 27 21  2  0
 10 16  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  6 36  1  1
  7 37  1  0
 20 44  1  6
 19 42  1  0
 19 43  1  0
 15 41  1  0
 13 40  1  0
 12 39  1  0
 11 38  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END


  Mrv1652309032220592D          

 27 31  0  0  0  0            999 V2000
   -0.2878    3.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    3.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239    3.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357    3.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1778    2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9475    2.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0502    1.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945    1.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8426    1.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6665    1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0424    1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5944    0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9703   -0.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7704    0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -0.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983   -0.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984    0.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    1.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385    2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2806    1.5639    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  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  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
  8 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1CC(O)C2=C3C(CC(=O)C4=C(O)C=CC=C34)C3=CC=C(O)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O5/c1-2-27-17-9-16(26)22-18-11-4-3-5-13(23)19(11)15(25)8-12(18)10-6-7-14(24)21(17)20(10)22/h3-7,12,16-17,23-24,26H,2,8-9H2,1H3

> <INCHI_KEY>
DSVFBOXMAJTYHV-UHFFFAOYSA-N

> <FORMULA>
C22H20O5

> <MOLECULAR_WEIGHT>
364.397

> <EXACT_MASS>
364.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.24164731355734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-ethoxy-7,15,19-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3,5,7,12,14,16(20)-heptaen-9-one

> <JCHEM_LOGP>
2.7119939389999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.55466822007658

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.919620533846329

> <JCHEM_PKA_STRONGEST_BASIC>
-3.086785806139983

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
101.57789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
17-ethoxy-7,15,19-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3,5,7,12,14,16(20)-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.537   6.787   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.661   5.820   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.098   6.375   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.297   5.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.733   5.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.932   4.995   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.369   5.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.694   3.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.665   2.279   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.203   2.201   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.040   3.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.578   3.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.279   2.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.443   0.752   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.144  -0.619   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.905   0.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.068  -0.463   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.770  -1.834   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.530  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.829   0.986   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.340   1.382   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.050   0.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.677   1.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.594   2.775   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.196   3.422   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.058   3.886   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.257   2.919   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   27                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    9   21                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    4   27                                                  
CONECT   27   26   21    8                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
3-Ethoxy-1,4,9-trihydroxy-1,2,3,6b-tetrahydrobenzo(J)fluoranthen-8(7H)-one	MeSH

Chemical Formula

C₂₂H₂₀O₅

Average Mass

364.3970 Da

Monoisotopic Mass

364.13107 Da

IUPAC Name

17-ethoxy-7,15,19-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3,5,7,12,14,16(20)-heptaen-9-one

Traditional Name

17-ethoxy-7,15,19-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3,5,7,12,14,16(20)-heptaen-9-one

CAS Registry Number

Not Available

SMILES

CCOC1CC(O)C2=C3C(CC(=O)C4=C(O)C=CC=C34)C3=CC=C(O)C1=C23

InChI Identifier

InChI=1S/C22H20O5/c1-2-27-17-9-16(26)22-18-11-4-3-5-13(23)19(11)15(25)8-12(18)10-6-7-14(24)21(17)20(10)22/h3-7,12,16-17,23-24,26H,2,8-9H2,1H3

InChI Key

DSVFBOXMAJTYHV-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

Species Name	Source	Reference
Annulohypoxylon truncatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Tetralin
Indene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Secondary alcohol
Ether
Dialkyl ether
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.71	ChemAxon
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.58 m³·mol⁻¹	ChemAxon
Polarizability	39.24 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

9123721

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10948496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang CW, Chang HS, Cheng MJ, Liu TW, Hsieh SY, Yuan GF, Chen IS: Inhibitory effects of constituents of an endophytic fungus Hypoxylon investiens on nitric oxide and interleukin-6 production in RAW264.7 macrophages. Chem Biodivers. 2014 Jun;11(6):949-61. doi: 10.1002/cbdv.201300364. [PubMed:24934680 ]
Baire B, Yadav B: TfOH catalysed domino-double annulation of arenes with propargylic alcohols: a unified approach to indene polycyclic systems. Chem Commun (Camb). 2021 Nov 30;57(95):12796-12799. doi: 10.1039/d1cc05253e. [PubMed:34782905 ]
LOTUS database [Link]

Showing NP-Card for 3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one (NP0180606)

MOL for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

3D MOL for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

3D SDF for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

3D-SDF for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

PDB for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

3D PDB for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

SMILES for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

INCHI for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

Structure for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)

3D Structure for NP0180606 (3-ethoxy-1,4,9-trihydroxy-1h,2h,3h,6bh,7h-benzo[j]fluoranthen-8-one)