NP-MRD: Showing NP-Card for Ravenelone (NP0004544)

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Record Information

Version

2.0

Created at

2020-12-09 02:00:38 UTC

Updated at

2021-07-15 16:49:28 UTC

NP-MRD ID

NP0004544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ravenelone

Provided By

NPAtlas

Description

Methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)-2,5-dihydrofuran-3-yl]-2,3-diphenylpropanoate belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Ravenelone is found in Pulveroboletus and Pulveroboletus ravenelii . Ravenelone was first documented in 2003 (PMID: 12612423). Based on a literature review very few articles have been published on methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)-2,5-dihydrofuran-3-yl]-2,3-diphenylpropanoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

 54 57  0  0  0  0            999 V2000
   -2.0083   -0.7367    3.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249    0.1775    2.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -0.2710    1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -1.5205    1.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    0.6910    0.3770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0518    1.4444    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    2.0220    1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    2.7883    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3962    2.9933    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893    2.4332   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    1.6829   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118073D          

 54 57  0  0  0  0            999 V2000
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   -1.9249    0.1775    2.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1652    1.9468    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    3.2453    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3133    3.5979    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4020    2.5955   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.2691   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.1155   -1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592    2.4585   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9649    2.0300   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -1.5945   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -2.8309    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -1.7197    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9104    0.6665    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770    1.8959    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600   -1.1178   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -2.9176   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -3.7473   -3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -2.7249   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -0.8617   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 11  6  1  0  0  0  0
 25 13  1  0  0  0  0
 32 27  1  0  0  0  0
 23 18  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  5 36  1  1  0  0  0
  7 37  1  0  0  0  0
  8 38  1  0  0  0  0
  9 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 12 42  1  6  0  0  0
 15 43  1  0  0  0  0
 17 44  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 47  1  0  0  0  0
 22 48  1  0  0  0  0
 23 49  1  0  0  0  0
 28 50  1  0  0  0  0
 29 51  1  0  0  0  0
 30 52  1  0  0  0  0
 31 53  1  0  0  0  0
 32 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)O\C1=C(\[H])C1=C([H])C([H])=C([H])C([H])=C1[H])[C@@]([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])[C@]([H])(C(=O)OC([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O5/c1-31-26(29)23(20-15-9-4-10-16-20)22(19-13-7-3-8-14-19)24-25(28)21(32-27(24)30)17-18-11-5-2-6-12-18/h2-17,22-23,28H,1H3/b21-17-/t22-,23+/m0/s1

> <INCHI_KEY>
DFRUUMWSIQRNGP-PCGCSWCKSA-N

> <FORMULA>
C27H22O5

> <MOLECULAR_WEIGHT>
426.468

> <EXACT_MASS>
426.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.29321795998846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)-2,5-dihydrofuran-3-yl]-2,3-diphenylpropanoate

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.897066909333334

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.527842324516618

> <JCHEM_PKA_STRONGEST_BASIC>
-6.504521767371565

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
122.97760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.0083   -0.7367    3.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249    0.1775    2.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -0.2710    1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -1.5205    1.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    0.6910    0.3770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0518    1.4444    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    2.0220    1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    2.7883    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3962    2.9933    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893    2.4332   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    1.6829   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    0.2639   -0.7432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4439    0.0249   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329    0.9304   -0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    2.2246   -0.9858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7061    0.3970   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    0.9933   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0733    0.2425    0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748   -1.0834   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998   -1.7819    0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560   -1.1640    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1588    0.1631    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0381    0.8594    1.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -0.9080    0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.1575    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -2.2895    0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.8252   -1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.4026   -1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1142   -2.4431   -2.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198   -2.9234   -3.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -2.3324   -3.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033   -1.2964   -2.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621   -0.3240    4.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -1.0752    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -1.6735    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296    1.5702    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.9468    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    3.2453    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3133    3.5979    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4020    2.5955   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.2691   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.1155   -1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592    2.4585   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9649    2.0300   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -1.5945   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -2.8309    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -1.7197    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9104    0.6665    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770    1.8959    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600   -1.1178   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -2.9176   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -3.7473   -3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -2.7249   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -0.8617   -2.8032 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 11  6  1  0
 25 13  1  0
 32 27  1  0
 23 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  6
 15 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.008  -0.737   3.911  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.925   0.178   2.839  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.913  -0.271   1.487  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.983  -1.521   1.410  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.822   0.691   0.377  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.052   1.444   0.227  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.584   2.022   1.365  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.746   2.788   1.310  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.396   2.993   0.120  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.889   2.433  -1.023  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.744   1.683  -0.942  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.022   0.264  -0.743  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.444   0.025  -0.421  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.433   0.930  -0.539  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.231   2.225  -0.986  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.706   0.397  -0.146  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.905   0.993  -0.129  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.073   0.243   0.315  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.275  -1.083  -0.001  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.400  -1.782   0.442  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.356  -1.164   1.216  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.159   0.163   1.535  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.038   0.859   1.094  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.487  -0.908   0.236  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.107  -1.157   0.076  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.643  -2.289   0.357  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.518  -0.825  -1.595  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.727  -1.403  -1.409  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.114  -2.443  -2.233  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.320  -2.923  -3.244  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.090  -2.332  -3.431  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.703  -1.296  -2.611  0.00  0.00           C+0
HETATM   33  H   UNK     0      -2.562  -0.324   4.752  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.973  -1.075   4.201  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.487  -1.674   3.501  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.130   1.570   0.864  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.165   1.947   2.358  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.167   3.245   2.217  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.313   3.598   0.081  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.402   2.595  -1.956  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.355   1.269  -1.858  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.904   1.115  -1.538  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.159   2.458  -1.984  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.965   2.030  -0.451  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.539  -1.595  -0.610  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.524  -2.831   0.172  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.220  -1.720   1.551  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.910   0.667   2.149  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.877   1.896   1.339  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.460  -1.118  -0.669  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.101  -2.918  -2.086  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.690  -3.747  -3.855  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.469  -2.725  -4.238  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.287  -0.862  -2.803  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12   36                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   38                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   11   40                                                  
CONECT   11   10    6   41                                                  
CONECT   12    5   13   27   42                                             
CONECT   13   12   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   43                                                       
CONECT   16   14   17   24                                                  
CONECT   17   16   18   44                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   45                                                  
CONECT   20   19   21   46                                                  
CONECT   21   20   22   47                                                  
CONECT   22   21   23   48                                                  
CONECT   23   22   18   49                                                  
CONECT   24   16   25                                                       
CONECT   25   24   26   13                                                  
CONECT   26   25                                                            
CONECT   27   12   28   32                                                  
CONECT   28   27   29   50                                                  
CONECT   29   28   30   51                                                  
CONECT   30   29   31   52                                                  
CONECT   31   30   32   53                                                  
CONECT   32   31   27   54                                                  
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   15                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   32                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -2.0083   -0.7367    3.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249    0.1775    2.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9834   -1.5205    1.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    0.6910    0.3770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0518    1.4444    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    2.0220    1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    2.7883    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8893    2.4332   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3560   -1.1640    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1588    0.1631    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0381    0.8594    1.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -0.9080    0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.1575    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -2.2895    0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.8252   -1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.4026   -1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1142   -2.4431   -2.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198   -2.9234   -3.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -2.3324   -3.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033   -1.2964   -2.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621   -0.3240    4.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -1.0752    4.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -1.6735    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296    1.5702    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.9468    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    3.2453    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3133    3.5979    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4020    2.5955   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.2691   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.1155   -1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592    2.4585   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9649    2.0300   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -1.5945   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -2.8309    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -1.7197    1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9104    0.6665    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770    1.8959    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600   -1.1178   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -2.9176   -2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -3.7473   -3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -2.7249   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -0.8617   -2.8032 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 11  6  1  0
 25 13  1  0
 32 27  1  0
 23 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  6
 15 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)-2,5-dihydrofuran-3-yl]-2,3-diphenylpropanoic acid	Generator

Chemical Formula

C₂₇H₂₂O₅

Average Mass

426.4680 Da

Monoisotopic Mass

426.14672 Da

IUPAC Name

methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)-2,5-dihydrofuran-3-yl]-2,3-diphenylpropanoate

Traditional Name

methyl (2S,3R)-3-[(5Z)-4-hydroxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]([C@@H](C1=C(O)\C(OC1=O)=C\C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H22O5/c1-31-26(29)23(20-15-9-4-10-16-20)22(19-13-7-3-8-14-19)24-25(28)21(32-27(24)30)17-18-11-5-2-6-12-18/h2-17,22-23,28H,1H3/b21-17-/t22-,23+/m0/s1

InChI Key

DFRUUMWSIQRNGP-PCGCSWCKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pulveroboletus	NPAtlas	12612423
Pulveroboletus ravenelii	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Fatty acid ester
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Dihydrofuran
Enol ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Lactone
Carboxylic acid ester
Oxacycle
Enol
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.95	ALOGPS
logP	4.9	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.53	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.98 m³·mol⁻¹	ChemAxon
Polarizability	45.29 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

NPAtlas ID

NPA000258

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101227982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Quang DN, Hashimoto T, Nukada M, Yamamoto I, Tanaka M, Takaoka S, Asakawa Y: Two novel ravenelones from the edible mushroom Pulveroboletus ravenelii. Chem Pharm Bull (Tokyo). 2003 Mar;51(3):330-2. doi: 10.1248/cpb.51.330. [PubMed:12612423 ]

Showing NP-Card for Ravenelone (NP0004544)

MOL for NP0004544 (Ravenelone)

3D MOL for NP0004544 (Ravenelone)

3D SDF for NP0004544 (Ravenelone)

3D-SDF for NP0004544 (Ravenelone)

PDB for NP0004544 (Ravenelone)

3D PDB for NP0004544 (Ravenelone)

SMILES for NP0004544 (Ravenelone)

INCHI for NP0004544 (Ravenelone)

Structure for NP0004544 (Ravenelone)

3D Structure for NP0004544 (Ravenelone)