NP-MRD: Showing NP-Card for brevipolide B (NP0034536)

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Record Information

Version

2.0

Created at

2021-06-20 18:14:17 UTC

Updated at

2024-09-03 04:15:36 UTC

NP-MRD ID

NP0034536

Natural Product DOI

https://doi.org/10.57994/0328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

brevipolide B

Provided By

JEOL Database JEOL Logo

Description

brevipolide B is found in Hyptis brevipes. brevipolide B was first documented in 2009 (Deng, Y., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120143D          

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M  END

     RDKit          3D

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  Mrv1652306202120143D          

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   -4.7670   -1.1427   -3.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -1.8474   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127   -0.2805   -3.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788    3.3108   -3.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    4.3611   -3.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    1.0838   -2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9227    0.4796   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    1.1830   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    4.4552   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    5.0878   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.1806    2.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -3.6621    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939   -3.5674    2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364   -4.3255    2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -2.6760    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 29 30  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
 29 31  1  0  0  0  0
  9 10  2  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
 28 27  2  0  0  0  0
 14 15  2  0  0  0  0
  6  8  1  0  0  0  0
 27 26  1  0  0  0  0
 24 18  1  0  0  0  0
  8  9  1  0  0  0  0
 18 19  2  0  0  0  0
 26 25  1  0  0  0  0
 19 20  1  0  0  0  0
  9 11  1  0  0  0  0
 20 21  2  0  0  0  0
 25 31  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11 13  1  0  0  0  0
 21 22  1  0  0  0  0
  5  4  1  0  0  0  0
 13 14  1  0  0  0  0
  8 39  1  1  0  0  0
 25  5  1  0  0  0  0
  6 36  1  6  0  0  0
 14 16  1  0  0  0  0
  4  2  1  0  0  0  0
 29 28  1  0  0  0  0
  2  3  2  0  0  0  0
 16 17  2  0  0  0  0
  2  1  1  0  0  0  0
 28 55  1  0  0  0  0
 27 54  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 25 51  1  1  0  0  0
  5 35  1  1  0  0  0
 11 40  1  1  0  0  0
 16 44  1  0  0  0  0
 17 45  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 24 50  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  0  0  0  0
 23 49  1  0  0  0  0
 22 48  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(\[H])C(=O)O[C@]([H])(C(=O)[C@@]2([H])C([H])([H])[C@]2([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2([H])OC(=O)C([H])=C([H])C2([H])[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O8/c1-13(29-21(27)11-8-15-6-9-16(25)10-7-15)22(28)17-12-18(17)23(30-14(2)24)19-4-3-5-20(26)31-19/h3,5-11,13,17-19,23,25H,4,12H2,1-2H3/b11-8-/t13-,17-,18-,19+,23-/m0/s1

> <INCHI_KEY>
HEYOPWSFHOXZQH-DKNNSNLISA-N

> <FORMULA>
C23H24O8

> <MOLECULAR_WEIGHT>
428.437

> <EXACT_MASS>
428.147117733

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.51909378288207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-(acetyloxy)[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.510623233999999

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.388272226368152

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398546952761246

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9547330563352405

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000003

> <JCHEM_REFRACTIVITY>
110.2643

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-(acetyloxy)[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -1.1524    2.2452    2.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    0.7637    2.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.1810    3.4847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    0.1602    1.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -1.2720    1.2186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1024   -1.7428   -0.1630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9416   -2.9747   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -1.6085   -0.6052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8342   -1.0932   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068   -1.3938   -2.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572   -0.1813   -2.1204 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1241   -0.9101   -2.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    1.0183   -2.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9304    1.8611   -2.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6243    1.7316   -0.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5188    2.9625   -3.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029    3.5303   -3.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447    3.1279   -2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856    1.8334   -2.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251    1.4859   -1.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1335    2.4324   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428    2.1352    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    3.7235   -0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    4.0738   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317   -1.6397    1.6027 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9687   -3.1471    1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -3.3997    1.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -2.5098    1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661   -1.2848    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029   -0.5557    0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6416   -1.0339    0.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3056    2.6283    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950    2.4804    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436    2.7245    3.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165   -1.7064    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464   -1.4923   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7159   -3.5769   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -3.5503    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -1.2808    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    0.0721   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670   -1.1427   -3.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -1.8474   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127   -0.2805   -3.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788    3.3108   -3.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    4.3611   -3.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    1.0838   -2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9227    0.4796   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    1.1830   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    4.4552   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    5.0878   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.1806    2.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -3.6621    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939   -3.5674    2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364   -4.3255    2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -2.6760    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 29 30  2  0
  6  7  1  0
  8  7  1  0
 29 31  1  0
  9 10  2  0
  5  6  1  0
 11 12  1  0
 28 27  2  0
 14 15  2  0
  6  8  1  0
 27 26  1  0
 24 18  1  0
  8  9  1  0
 18 19  2  0
 26 25  1  0
 19 20  1  0
  9 11  1  0
 20 21  2  0
 25 31  1  0
 21 23  1  0
 23 24  2  0
 11 13  1  0
 21 22  1  0
  5  4  1  0
 13 14  1  0
  8 39  1  1
 25  5  1  0
  6 36  1  6
 14 16  1  0
  4  2  1  0
 29 28  1  0
  2  3  2  0
 16 17  2  0
  2  1  1  0
 28 55  1  0
 27 54  1  0
 26 52  1  0
 26 53  1  0
 25 51  1  1
  5 35  1  1
 11 40  1  1
 16 44  1  0
 17 45  1  0
  7 37  1  0
  7 38  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 24 50  1  0
 19 46  1  0
 20 47  1  0
 23 49  1  0
 22 48  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.152   2.245   2.238  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.024   0.764   2.409  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.060   0.181   3.485  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.874   0.160   1.205  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.721  -1.272   1.219  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.102  -1.743  -0.163  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.942  -2.975  -0.394  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.550  -1.609  -0.605  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.834  -1.093  -1.979  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.107  -1.394  -2.922  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.057  -0.181  -2.120  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.124  -0.910  -2.925  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.719   1.018  -2.827  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.930   1.861  -2.112  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.624   1.732  -0.940  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.519   2.962  -3.002  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.303   3.530  -3.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.145   3.128  -2.195  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.386   1.833  -2.280  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.525   1.486  -1.549  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.134   2.432  -0.733  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.243   2.135   0.002  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.626   3.724  -0.647  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.490   4.074  -1.381  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.732  -1.640   1.603  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.969  -3.147   1.685  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.430  -3.400   1.891  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.349  -2.510   1.490  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.966  -1.285   0.763  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.803  -0.556   0.243  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.642  -1.034   0.654  0.00  0.00           O+0
HETATM   32  H   UNK     0      -0.306   2.628   1.664  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.095   2.480   1.739  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.144   2.724   3.221  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.417  -1.706   1.949  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.346  -1.492  -0.902  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.716  -3.577  -1.269  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.277  -3.550   0.460  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.255  -1.281   0.154  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.475   0.072  -1.139  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.767  -1.143  -3.935  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.417  -1.847  -2.442  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.013  -0.281  -3.041  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.279   3.311  -3.692  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.113   4.361  -3.676  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.075   1.084  -2.920  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.923   0.480  -1.632  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.457   1.183  -0.104  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.115   4.455  -0.011  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.105   5.088  -1.308  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.960  -1.181   2.574  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.664  -3.662   0.768  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.394  -3.567   2.518  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.736  -4.325   2.369  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.411  -2.676   1.619  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   25   35                                             
CONECT    6    7    5    8   36                                             
CONECT    7    6    8   37   38                                             
CONECT    8    7    6    9   39                                             
CONECT    9   10    8   11                                                  
CONECT   10    9                                                            
CONECT   11   12    9   13   40                                             
CONECT   12   11   41   42   43                                             
CONECT   13   11   14                                                       
CONECT   14   15   13   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   44                                                  
CONECT   17   18   16   45                                                  
CONECT   18   17   24   19                                                  
CONECT   19   18   20   46                                                  
CONECT   20   19   21   47                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21   48                                                       
CONECT   23   21   24   49                                                  
CONECT   24   18   23   50                                                  
CONECT   25   26   31    5   51                                             
CONECT   26   27   25   52   53                                             
CONECT   27   28   26   54                                                  
CONECT   28   27   29   55                                                  
CONECT   29   30   31   28                                                  
CONECT   30   29                                                            
CONECT   31   29   25                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
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    3.2428    2.1352    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    3.7235   -0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    4.0738   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317   -1.6397    1.6027 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9687   -3.1471    1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -3.3997    1.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -2.5098    1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661   -1.2848    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029   -0.5557    0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6416   -1.0339    0.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3464   -1.4923   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7159   -3.5769   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -3.5503    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -1.2808    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    0.0721   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670   -1.1427   -3.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -1.8474   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127   -0.2805   -3.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788    3.3108   -3.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    4.3611   -3.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    1.0838   -2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9227    0.4796   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    1.1830   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    4.4552   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    5.0878   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.1806    2.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -3.6621    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939   -3.5674    2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364   -4.3255    2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -2.6760    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  2  0
  6  7  1  0
  8  7  1  0
 29 31  1  0
  9 10  2  0
  5  6  1  0
 11 12  1  0
 28 27  2  0
 14 15  2  0
  6  8  1  0
 27 26  1  0
 24 18  1  0
  8  9  1  0
 18 19  2  0
 26 25  1  0
 19 20  1  0
  9 11  1  0
 20 21  2  0
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 21 23  1  0
 23 24  2  0
 11 13  1  0
 21 22  1  0
  5  4  1  0
 13 14  1  0
  8 39  1  1
 25  5  1  0
  6 36  1  6
 14 16  1  0
  4  2  1  0
 29 28  1  0
  2  3  2  0
 16 17  2  0
  2  1  1  0
 28 55  1  0
 27 54  1  0
 26 52  1  0
 26 53  1  0
 25 51  1  1
  5 35  1  1
 11 40  1  1
 16 44  1  0
 17 45  1  0
  7 37  1  0
  7 38  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 24 50  1  0
 19 46  1  0
 20 47  1  0
 23 49  1  0
 22 48  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₈

Average Mass

428.4370 Da

Monoisotopic Mass

428.14712 Da

IUPAC Name

(2S)-1-[(1S,2S)-2-[(S)-(acetyloxy)[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S)-1-[(1S,2S)-2-[(S)-(acetyloxy)[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(\[H])C(=O)O[C@]([H])(C(=O)[C@@]2([H])C([H])([H])[C@]2([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2([H])OC(=O)C([H])=C([H])C2([H])[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C23H24O8/c1-13(29-21(27)11-8-15-6-9-16(25)10-7-15)22(28)17-12-18(17)23(30-14(2)24)19-4-3-5-20(26)31-19/h3,5-11,13,17-19,23,25H,4,12H2,1-2H3/b11-8-/t13-,17-,18-,19+,23-/m0/s1

InChI Key

HEYOPWSFHOXZQH-DKNNSNLISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Hyptis brevipes	JEOL database	Deng, Y., et al, J. Nat. Prod. 72, 1165 (2009)

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	2.46	ALOGPS
logP	3.51	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	110.26 m³·mol⁻¹	ChemAxon
Polarizability	42.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Deng, Y., et al. (2009). Deng, Y., et al, J. Nat. Prod. 72, 1165 (2009). J. Nat. Prod..
DOI: 10.1021/acs.jnatprod.2c00146
PMID: 35640148

Showing NP-Card for brevipolide B (NP0034536)

MOL for NP0034536 (brevipolide B)

3D MOL for NP0034536 (brevipolide B)

3D SDF for NP0034536 (brevipolide B)

3D-SDF for NP0034536 (brevipolide B)

PDB for NP0034536 (brevipolide B)

3D PDB for NP0034536 (brevipolide B)

SMILES for NP0034536 (brevipolide B)

INCHI for NP0034536 (brevipolide B)

Structure for NP0034536 (brevipolide B)

3D Structure for NP0034536 (brevipolide B)