NP-MRD: Showing NP-Card for (1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate (NP0154344)

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Record Information

Version

2.0

Created at

2022-09-02 11:08:09 UTC

Updated at

2022-09-02 11:08:09 UTC

NP-MRD ID

NP0154344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate

Description

Pectinolide E, also known as hypurticin, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate was first documented in 2003 (PMID: 14599529). Based on a literature review a small amount of articles have been published on Pectinolide E (PMID: 19265396) (PMID: 31192696).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213082D          

 28 28  0  0  1  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1105    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END

     RDKit          3D

 52 52  0  0  0  0  0  0  0  0999 V2000
    0.8632    4.6250   -1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385    3.5799   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671    3.8244    0.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271    2.2490   -0.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726    1.2114   -0.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7381    0.3732    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817    0.1510   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9462   -0.6860    0.4889 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8682    0.1304    1.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8629   -0.5787    1.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -0.2025    2.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2938   -1.8303    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7715   -2.2437    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.4528   -0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4265   -0.5296   -1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283    0.3759   -1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8375   -0.8012   -0.5732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4923   -1.3034   -1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039   -1.7648   -0.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044   -3.0427    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0612   -3.8485    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177   -3.6104    0.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9495   -0.3147    0.3009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0206   -1.3700    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507    0.7722   -0.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    1.9201    0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5858    3.1089   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997    2.0043    1.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960    4.2998   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720    5.5715   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    4.9183   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0135    1.6227    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -0.0606    1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.5892   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -1.3959    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0762   -2.4437    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0883   -3.1703   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687   -2.0742   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387   -0.8461   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    0.9389   -1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -0.0894   -1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8536   -1.8084   -2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0387   -4.8553    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -3.9968    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0145   -3.4099    0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352    0.0368    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -2.0089   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -0.7626    0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8128   -1.9538    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737    3.2566   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6693    2.8715   -0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    4.0242    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 23 17  1  0
 17 18  1  6
 17 16  1  0
 16  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 14  8  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 23 46  1  1
 27 50  1  0
 27 51  1  0
 27 52  1  0
 18 42  1  0
 16 40  1  0
 16 41  1  0
  5 32  1  1
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  1
 12 36  1  0
 13 37  1  0
 14 38  1  6
 15 39  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END


  Mrv1652309022213082D          

 28 28  0  0  1  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1105    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0154344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](OC(C)=O)[C@@](O)(C[C@H](OC(C)=O)\C=C\[C@@H]1OC(=O)C=C[C@@H]1O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O10/c1-10(25-11(2)19)18(24,28-13(4)21)9-14(26-12(3)20)5-7-16-15(22)6-8-17(23)27-16/h5-8,10,14-16,22,24H,9H2,1-4H3/b7-5+/t10-,14+,15-,16-,18+/m0/s1

> <INCHI_KEY>
XPJKRRDFFPYURY-GJNHSSSJSA-N

> <FORMULA>
C18H24O10

> <MOLECULAR_WEIGHT>
400.38

> <EXACT_MASS>
400.136946973

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.79603621546321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,3S,5R,6S)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2S,3S)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-1-en-3-yl acetate

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.3630618289999996

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.681200843279598

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.866661493945543

> <JCHEM_PKA_STRONGEST_BASIC>
-3.375918214926468

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
93.2084

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,3S,5R,6S)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2S,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.206   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.874   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.644   7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.874   5.803   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.184   7.136   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  13.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
Hypurticin	MeSH
6S-(3's,5'r,6's-Triacetoxy-1Z-heptenyl)-5S-acetoxy-5,6-dihydro-2H-pyran-2-one	MeSH

Chemical Formula

C₁₈H₂₄O₁₀

Average Mass

400.3800 Da

Monoisotopic Mass

400.13695 Da

IUPAC Name

(1E,3S,5R,6S)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2S,3S)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-1-en-3-yl acetate

Traditional Name

(1E,3S,5R,6S)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2S,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](OC(C)=O)[C@@](O)(C[C@H](OC(C)=O)\C=C\[C@@H]1OC(=O)C=C[C@@H]1O)OC(C)=O

InChI Identifier

InChI=1S/C18H24O10/c1-10(25-11(2)19)18(24,28-13(4)21)9-14(26-12(3)20)5-7-16-15(22)6-8-17(23)27-16/h5-8,10,14-16,22,24H,9H2,1-4H3/b7-5+/t10-,14+,15-,16-,18+/m0/s1

InChI Key

XPJKRRDFFPYURY-GJNHSSSJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Dihydropyranone
Pyran
Hemiketal
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	0.28	ALOGPS
logP	0.36	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	93.21 m³·mol⁻¹	ChemAxon
Polarizability	38.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036193

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101267305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Boalino DM, Connolly JD, McLean S, Reynolds WF, Tinto WF: Alpha-pyrones and a 2(5H)-furanone from Hyptis pectinata. Phytochemistry. 2003 Dec;64(7):1303-7. doi: 10.1016/j.phytochem.2003.08.017. [PubMed:14599529 ]
Mendoza-Espinoza JA, Lopez-Vallejo F, Fragoso-Serrano M, Pereda-Miranda R, Cerda-Garcia-Rojas CM: Structural reassignment, absolute configuration, and conformation of hypurticin, a highly flexible polyacyloxy-6-heptenyl-5,6-dihydro-2H-pyran-2-one. J Nat Prod. 2009 Apr;72(4):700-8. doi: 10.1021/np800447k. [PubMed:19265396 ]
Santana FR, Luna-Dulcey L, Antunes VU, Tormena CF, Cominetti MR, Duarte MC, da Silva JA: Evaluation of the cytotoxicity on breast cancer cell of extracts and compounds isolated from Hyptis pectinata (L.) poit. Nat Prod Res. 2020 Jan;34(1):102-109. doi: 10.1080/14786419.2019.1628747. Epub 2019 Jun 13. [PubMed:31192696 ]
LOTUS database [Link]

Showing NP-Card for (1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate (NP0154344)

MOL for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

3D MOL for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

3D SDF for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

3D-SDF for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

PDB for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

3D PDB for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

SMILES for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

INCHI for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

Structure for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)

3D Structure for NP0154344 ((1e,3s,5r,6s)-5,6-bis(acetyloxy)-5-hydroxy-1-[(2s,3s)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl acetate)