NP-MRD: Showing NP-Card for methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate (NP0167051)

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Record Information

Version

2.0

Created at

2022-09-03 02:34:07 UTC

Updated at

2022-09-03 02:34:07 UTC

NP-MRD ID

NP0167051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate

Description

(AlphaS,betaR)-alpha,beta-Diphenyl-2-oxo-4-methoxy-5-[(E)-benzylidene]-2,5-dihydrofuran-3-propionic acid methyl ester 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. methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate is found in Pulveroboletus ravenelii. Based on a literature review very few articles have been published on (alphaS,betaR)-alpha,beta-Diphenyl-2-oxo-4-methoxy-5-[(E)-benzylidene]-2,5-dihydrofuran-3-propionic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032204342D          

 33 36  0  0  1  0            999 V2000
   -0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -3.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0902   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9106   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -3.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    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  2  0  0  0  0
  5  3  1  6  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
  6 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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
 19 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.2668   -0.1557    4.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5114    0.3367    2.9083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4110   -0.3714    1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9742   -1.4592    1.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6086    0.1841    0.5663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7705   -0.7070   -0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8742   -1.6779   -0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219   -2.5321   -2.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -2.4284   -2.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -1.4584   -2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -0.6112   -1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    0.6500    0.8927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2315   -0.2729    1.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672   -0.3171    0.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094    0.5206    0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378    0.1139   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7621   -1.3496    1.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.7373    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851   -1.0895    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311    0.2619    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1445    0.8660   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8173    0.1054   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5759   -1.2555   -1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699   -1.8283   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482   -1.9558    2.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -1.3095    2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -1.6783    3.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695    1.7487    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123    1.8703   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    2.9202   -2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1737    3.8694   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439    3.7750   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    2.7451    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.4764    4.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498   -0.1202    3.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -1.1932    4.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    1.1453    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672   -1.8371   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863   -3.2846   -2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -3.1031   -3.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9238   -1.4061   -3.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    0.1240   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    1.2647    1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -0.1339   -1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -0.7930   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    0.9686   -1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3502   -2.5818    2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    0.8886    1.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    1.9249   -0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5298    0.5809   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185   -1.8205   -1.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4868   -2.8892   -0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    1.1686   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9465    2.9830   -3.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    4.6827   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032    4.5313    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    2.6514    1.5811 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 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  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
 26 13  1  0
 24 19  1  0
 33 28  1  0
 11  6  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  6
 12 43  1  1
 16 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 32 56  1  0
 33 57  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
M  END


  Mrv1652309032204342D          

 33 36  0  0  1  0            999 V2000
   -0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -3.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0902   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9106   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -3.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    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  2  0  0  0  0
  5  3  1  6  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
  6 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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
 19 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167051

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O5/c1-31-26-22(18-19-12-6-3-7-13-19)33-28(30)25(26)23(20-14-8-4-9-15-20)24(27(29)32-2)21-16-10-5-11-17-21/h3-18,23-24H,1-2H3/b22-18+/t23-,24+/m0/s1

> <INCHI_KEY>
ZDYAFMHRSFOATI-PWNKNYCBSA-N

> <FORMULA>
C28H24O5

> <MOLECULAR_WEIGHT>
440.495

> <EXACT_MASS>
440.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.55441274570598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
5.0098942986666675

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9065499277079825

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
127.72880000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.73e-04 g/l

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

> <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      -0.199  -3.195   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.134  -2.425   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.199  -0.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.134   3.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.468   4.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.512  -2.854   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.477  -6.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.009  -5.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.635  -4.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.167  -4.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.072  -5.558   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.445  -6.965   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.914  -7.126   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.016  -3.330   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    5   13   28                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   17   26                                                       
CONECT   26   25   13   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(AlphaS,betar)-a,b-diphenyl-2-oxo-4-methoxy-5-[(e)-benzylidene]-2,5-dihydrofuran-3-propionate methyl ester	Generator
(AlphaS,betar)-a,b-diphenyl-2-oxo-4-methoxy-5-[(e)-benzylidene]-2,5-dihydrofuran-3-propionic acid methyl ester	Generator
(AlphaS,betar)-alpha,beta-diphenyl-2-oxo-4-methoxy-5-[(e)-benzylidene]-2,5-dihydrofuran-3-propionate methyl ester	Generator
(AlphaS,betar)-α,β-diphenyl-2-oxo-4-methoxy-5-[(e)-benzylidene]-2,5-dihydrofuran-3-propionate methyl ester	Generator
(AlphaS,betar)-α,β-diphenyl-2-oxo-4-methoxy-5-[(e)-benzylidene]-2,5-dihydrofuran-3-propionic acid methyl ester	Generator

Chemical Formula

C₂₈H₂₄O₅

Average Mass

440.4950 Da

Monoisotopic Mass

440.16237 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H24O5/c1-31-26-22(18-19-12-6-3-7-13-19)33-28(30)25(26)23(20-14-8-4-9-15-20)24(27(29)32-2)21-16-10-5-11-17-21/h3-18,23-24H,1-2H3/b22-18+/t23-,24+/m0/s1

InChI Key

ZDYAFMHRSFOATI-PWNKNYCBSA-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
Pulveroboletus ravenelii	LOTUS Database	35616633

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
Benzenoid
Fatty acyl
Vinylogous ester
Dihydrofuran
Enol ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	5.87	ALOGPS
logP	5.01	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.73 m³·mol⁻¹	ChemAxon
Polarizability	46.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9114337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10939102

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate (NP0167051)

MOL for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

3D MOL for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

3D SDF for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

3D-SDF for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

PDB for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

3D PDB for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

SMILES for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

INCHI for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

Structure for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)

3D Structure for NP0167051 (methyl (2s,3r)-3-[(5e)-4-methoxy-2-oxo-5-(phenylmethylidene)furan-3-yl]-2,3-diphenylpropanoate)