NP-MRD: Showing NP-Card for (2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+ (NP0040706)

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Record Information

Version

2.0

Created at

2021-06-20 22:47:45 UTC

Updated at

2021-06-30 00:14:46 UTC

NP-MRD ID

NP0040706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+

Provided By

JEOL Database JEOL Logo

Description

(2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+ is found in Mexican propolis. (2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+ was first documented in 2011 (Li, F. et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100473D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212100473D          

 59 62  0  0  0  0            999 V2000
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   -2.0562    2.2591    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0579    3.4001    0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1432    4.2000   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    5.2606   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8765    5.5375    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    4.7548    1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    3.6932    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    1.5114   -0.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3514   -2.3216   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -2.2097   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -2.5288   -3.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -2.6005   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -5.0256   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -7.2384   -2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -7.8541    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -4.7102    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673   -4.1855    2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0181   -5.4865    3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -3.5876    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -3.2921   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715   -0.4243   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.0926    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035    3.3968   -0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    4.3381    3.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655    5.5945    3.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    5.8377    3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3719    1.5941    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078    3.9992   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    5.8702   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5817    6.3630   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    4.9718    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    3.0990    2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 14  2  0  0  0  0
 13  3  1  0  0  0  0
 17 35  1  0  0  0  0
  3  4  1  0  0  0  0
 18 21  1  0  0  0  0
  4  5  2  0  0  0  0
 21 23  1  0  0  0  0
  5  6  1  0  0  0  0
 23 28  1  0  0  0  0
  6  7  2  0  0  0  0
 28 35  1  0  0  0  0
  7  9  1  0  0  0  0
 17 18  2  0  0  0  0
  9 12  2  0  0  0  0
 12  4  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  2  3  0  0  0
 29 30  2  0  0  0  0
  9 10  1  0  0  0  0
 13 19  2  0  0  0  0
  7  8  1  0  0  0  0
 30 31  1  0  0  0  0
 14 15  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 31 32  2  0  0  0  0
 21 22  2  0  0  0  0
 14 13  1  0  0  0  0
 10 11  1  0  0  0  0
 32 33  1  0  0  0  0
 23 24  1  0  0  0  0
 17 16  1  0  0  0  0
 24 25  1  0  0  0  0
 33 34  2  0  0  0  0
 25 26  1  0  0  0  0
 34 29  1  0  0  0  0
 25 27  2  0  0  0  0
 16 48  1  0  0  0  0
 23 50  1  6  0  0  0
 28 54  1  1  0  0  0
 30 55  1  0  0  0  0
 31 56  1  0  0  0  0
 32 57  1  0  0  0  0
 33 58  1  0  0  0  0
 34 59  1  0  0  0  0
  3 39  1  1  0  0  0
  5 40  1  0  0  0  0
  6 41  1  0  0  0  0
 12 46  1  0  0  0  0
  2 38  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  8 42  1  0  0  0  0
 15 47  1  0  0  0  0
 20 49  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
 11 45  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]([H])(C([H])=C([H])[H])C1=C(O[H])C2=C(O[C@]([H])(C3=C([H])C([H])=C([H])C([H])=C3[H])[C@@]([H])(OC(=O)C([H])([H])[H])C2=O)C([H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O8/c1-4-17(16-10-11-18(29)20(12-16)33-3)22-19(30)13-21-23(24(22)31)25(32)27(34-14(2)28)26(35-21)15-8-6-5-7-9-15/h4-13,17,26-27,29-31H,1H2,2-3H3/t17-,26-,27+/m1/s1

> <INCHI_KEY>
BOOMCYYMRWSEAS-TZPLSLOTSA-N

> <FORMULA>
C27H24O8

> <MOLECULAR_WEIGHT>
476.481

> <EXACT_MASS>
476.147117733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
49.98150872482919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-5,7-dihydroxy-6-[(1R)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-3-yl acetate

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
4.922797536333334

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.073709907926578

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.499831771693056

> <JCHEM_PKA_STRONGEST_BASIC>
-4.625746445535977

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000002

> <JCHEM_REFRACTIVITY>
127.1736

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-5,7-dihydroxy-6-[(1R)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    3.6486   -2.3468   -3.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -2.5310   -3.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1426   -6.6596   -0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0778   -5.6530    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5487   -5.0349    2.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -4.3905   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -1.6082   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -1.5194   -2.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -2.4336   -3.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572   -0.4626   -2.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    0.5261   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124    0.4731   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8894   -0.5911   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450   -0.6708    0.2177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645    1.5681    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    1.4524    1.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390    2.7846    0.5183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5787    3.5014    1.7605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941    4.4505    1.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    5.0931    3.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    4.7506    0.9194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    2.2591    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0579    3.4001    0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1432    4.2000   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    5.2606   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8765    5.5375    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    4.7548    1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    3.6932    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    1.5114   -0.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3514   -2.3216   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -2.2097   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -2.5288   -3.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -2.6005   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -5.0256   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -7.2384   -2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -7.8541    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -4.7102    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673   -4.1855    2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0181   -5.4865    3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -3.5876    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -3.2921   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715   -0.4243   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.0926    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035    3.3968   -0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    4.3381    3.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655    5.5945    3.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    5.8377    3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3719    1.5941    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078    3.9992   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    5.8702   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5817    6.3630   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    4.9718    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    3.0990    2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 14  2  0
 13  3  1  0
 17 35  1  0
  3  4  1  0
 18 21  1  0
  4  5  2  0
 21 23  1  0
  5  6  1  0
 23 28  1  0
  6  7  2  0
 28 35  1  0
  7  9  1  0
 17 18  2  0
  9 12  2  0
 12  4  1  0
 28 29  1  0
  3  2  1  0
  2  1  2  3
 29 30  2  0
  9 10  1  0
 13 19  2  0
  7  8  1  0
 30 31  1  0
 14 15  1  0
 19 18  1  0
 19 20  1  0
 31 32  2  0
 21 22  2  0
 14 13  1  0
 10 11  1  0
 32 33  1  0
 23 24  1  0
 17 16  1  0
 24 25  1  0
 33 34  2  0
 25 26  1  0
 34 29  1  0
 25 27  2  0
 16 48  1  0
 23 50  1  6
 28 54  1  1
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
 34 59  1  0
  3 39  1  1
  5 40  1  0
  6 41  1  0
 12 46  1  0
  2 38  1  0
  1 36  1  0
  1 37  1  0
  8 42  1  0
 15 47  1  0
 20 49  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.649  -2.347  -3.258  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.335  -2.531  -3.062  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.684  -2.710  -1.698  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.145  -4.122  -1.413  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.212  -5.170  -2.350  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.705  -6.433  -2.045  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.143  -6.660  -0.797  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.348  -7.908  -0.527  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.078  -5.653   0.169  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.495  -6.026   1.358  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.549  -5.035   2.378  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.585  -4.391  -0.143  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.639  -1.608  -1.467  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.562  -1.519  -2.197  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.949  -2.434  -3.137  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.457  -0.463  -2.013  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.192   0.526  -1.073  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.012   0.473  -0.338  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.889  -0.591  -0.522  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.045  -0.671   0.218  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.265   1.568   0.610  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.200   1.452   1.401  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.639   2.785   0.518  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.579   3.501   1.761  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.394   4.450   1.827  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.391   5.093   3.180  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.156   4.751   0.919  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.056   2.259   0.274  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.058   3.400   0.178  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.143   4.200  -0.973  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.048   5.261  -1.036  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.877   5.537   0.049  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.801   4.755   1.199  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.897   3.693   1.265  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.133   1.511  -0.953  0.00  0.00           O+0
HETATM   36  H   UNK     0       4.351  -2.322  -2.430  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.048  -2.210  -4.258  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.682  -2.529  -3.933  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.490  -2.600  -0.959  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.665  -5.026  -3.329  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.756  -7.238  -2.772  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.679  -7.854   0.391  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.456  -4.710   2.667  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.167  -4.186   2.070  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.018  -5.487   3.257  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.563  -3.588   0.589  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.536  -3.292  -2.947  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.372  -0.424  -2.602  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.083   0.093   0.839  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.304   3.397  -0.329  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.571   4.338   3.949  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.566   5.595   3.349  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.190   5.838   3.229  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.372   1.594   1.092  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.508   3.999  -1.834  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.108   5.870  -1.935  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.582   6.363  -0.002  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.448   4.972   2.046  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.851   3.099   2.175  0.00  0.00           H+0
CONECT    1    2   36   37                                                  
CONECT    2    3    1   38                                                  
CONECT    3   13    4    2   39                                             
CONECT    4    3    5   12                                                  
CONECT    5    4    6   40                                                  
CONECT    6    5    7   41                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7   42                                                       
CONECT    9    7   12   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   43   44   45                                             
CONECT   12    9    4   46                                                  
CONECT   13    3   19   14                                                  
CONECT   14   16   15   13                                                  
CONECT   15   14   47                                                       
CONECT   16   14   17   48                                                  
CONECT   17   35   18   16                                                  
CONECT   18   21   17   19                                                  
CONECT   19   13   18   20                                                  
CONECT   20   19   49                                                       
CONECT   21   18   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   28   24   50                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   51   52   53                                             
CONECT   27   25                                                            
CONECT   28   23   35   29   54                                             
CONECT   29   28   30   34                                                  
CONECT   30   29   31   55                                                  
CONECT   31   30   32   56                                                  
CONECT   32   31   33   57                                                  
CONECT   33   32   34   58                                                  
CONECT   34   33   29   59                                                  
CONECT   35   17   28                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    3                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   20                                                            
CONECT   50   23                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
    3.6486   -2.3468   -3.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -2.5310   -3.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -2.7097   -1.6978 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1451   -4.1218   -1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -5.1695   -2.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054   -6.4329   -2.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426   -6.6596   -0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475   -7.9082   -0.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5845   -4.3905   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -1.6082   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -1.5194   -2.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4572   -0.4626   -2.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    0.5261   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124    0.4731   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8894   -0.5911   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450   -0.6708    0.2177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645    1.5681    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    1.4524    1.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390    2.7846    0.5183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5787    3.5014    1.7605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941    4.4505    1.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    5.0931    3.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    4.7506    0.9194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    2.2591    0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0579    3.4001    0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1432    4.2000   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484    5.2606   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8765    5.5375    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    4.7548    1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    3.6932    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    1.5114   -0.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3514   -2.3216   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -2.2097   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -2.5288   -3.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -2.6005   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -5.0256   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -7.2384   -2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -7.8541    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -4.7102    2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673   -4.1855    2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0181   -5.4865    3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -3.5876    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -3.2921   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715   -0.4243   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.0926    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035    3.3968   -0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    4.3381    3.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655    5.5945    3.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902    5.8377    3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3719    1.5941    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078    3.9992   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    5.8702   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5817    6.3630   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    4.9718    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    3.0990    2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 14  2  0
 13  3  1  0
 17 35  1  0
  3  4  1  0
 18 21  1  0
  4  5  2  0
 21 23  1  0
  5  6  1  0
 23 28  1  0
  6  7  2  0
 28 35  1  0
  7  9  1  0
 17 18  2  0
  9 12  2  0
 12  4  1  0
 28 29  1  0
  3  2  1  0
  2  1  2  3
 29 30  2  0
  9 10  1  0
 13 19  2  0
  7  8  1  0
 30 31  1  0
 14 15  1  0
 19 18  1  0
 19 20  1  0
 31 32  2  0
 21 22  2  0
 14 13  1  0
 10 11  1  0
 32 33  1  0
 23 24  1  0
 17 16  1  0
 24 25  1  0
 33 34  2  0
 25 26  1  0
 34 29  1  0
 25 27  2  0
 16 48  1  0
 23 50  1  6
 28 54  1  1
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
 34 59  1  0
  3 39  1  1
  5 40  1  0
  6 41  1  0
 12 46  1  0
  2 38  1  0
  1 36  1  0
  1 37  1  0
  8 42  1  0
 15 47  1  0
 20 49  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₈

Average Mass

476.4810 Da

Monoisotopic Mass

476.14712 Da

IUPAC Name

(2R,3R)-5,7-dihydroxy-6-[(1R)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-3-yl acetate

Traditional Name

(2R,3R)-5,7-dihydroxy-6-[(1R)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]([H])(C([H])=C([H])[H])C1=C(O[H])C2=C(O[C@]([H])(C3=C([H])C([H])=C([H])C([H])=C3[H])[C@@]([H])(OC(=O)C([H])([H])[H])C2=O)C([H])=C1O[H]

InChI Identifier

InChI=1S/C27H24O8/c1-4-17(16-10-11-18(29)20(12-16)33-3)22-19(30)13-21-23(24(22)31)25(32)27(34-14(2)28)26(35-21)15-8-6-5-7-9-15/h4-13,17,26-27,29-31H,1H2,2-3H3/t17-,26-,27+/m1/s1

InChI Key

BOOMCYYMRWSEAS-TZPLSLOTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mexican propolis	JEOL database	Li, F. et al, Chem. Pharm. Bull. 59, 1194 (2011)

Chemical Taxonomy

Classification

Not classified

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	ALOGPS
logP	4.92	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.17 m³·mol⁻¹	ChemAxon
Polarizability	49.98 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

Not Available

References

General References

Li, F. et al. (2011). Li, F. et al, Chem. Pharm. Bull. 59, 1194 (2011). Chem. Pharm. Bull..

Showing NP-Card for (2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+ (NP0040706)

MOL for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

3D MOL for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

3D SDF for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

3D-SDF for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

PDB for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

3D PDB for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

SMILES for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

INCHI for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

Structure for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)

3D Structure for NP0040706 ((2R,3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]pinobanksin 3-ac+)