NP-MRD: Showing NP-Card for ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate (NP0160865)

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Record Information

Version

2.0

Created at

2022-09-02 18:54:56 UTC

Updated at

2022-09-02 18:54:56 UTC

NP-MRD ID

NP0160865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate

Description

Ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacos-16(20)-en-17-yl]acetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate is found in Schisandra rubriflora. Based on a literature review very few articles have been published on ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacos-16(20)-en-17-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220542D          

 41 47  0  0  1  0            999 V2000
   11.2480   -2.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1860   -1.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4425   -1.3555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3804   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0618   -0.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6369   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5749    0.6474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2040    1.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8907    1.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6825    2.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7430    2.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0680    1.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    0.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180    1.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3756    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8224   -0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9754   -0.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2761   -1.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -0.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -1.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608   -0.6304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9573   -1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    0.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5433    0.4323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8187    1.2796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1501    1.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498    1.6019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6557    2.0479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6085    2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0171    1.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    1.7352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402    0.8040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5474    1.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768    2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9065    2.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1607    1.9573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7409    2.5659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4257    3.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5725    2.5449    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
 25 24  1  6  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 34 33  1  1  0  0  0
 24 34  1  0  0  0  0
 28 34  1  0  0  0  0
 26 35  1  6  0  0  0
 15 35  1  6  0  0  0
 26 36  1  0  0  0  0
 36 37  2  0  0  0  0
 38 36  1  6  0  0  0
 15 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 12 41  1  0  0  0  0
M  END

     RDKit          3D

 81 87  0  0  0  0  0  0  0  0999 V2000
    9.1352    0.2849   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9984   -0.3687   -1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494    0.2590   -1.0634 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5684   -1.1412   -2.3871 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0930    1.3476    2.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -0.8677    3.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346    0.0102    1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928   -0.0119    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8522   -0.4362    2.4595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7257   -1.8858    2.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5441   -2.1910    2.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2005   -0.0471    3.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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  4  6  1  0
  6  7  1  0
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  9 11  1  0
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 13  7  1  0
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 39 78  1  1
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 41 80  1  0
 41 81  1  0
M  END


  Mrv1652309022220542D          

 41 47  0  0  1  0            999 V2000
   11.2480   -2.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1860   -1.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4425   -1.3555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3804   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0618   -0.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6369   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5749    0.6474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2040    1.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8907    1.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6825    2.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7430    2.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0680    1.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    0.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180    1.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3756    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8224   -0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9754   -0.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2761   -1.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -0.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -1.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608   -0.6304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9573   -1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    0.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5433    0.4323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8187    1.2796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1501    1.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498    1.6019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6557    2.0479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6085    2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0171    1.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    1.7352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402    0.8040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5474    1.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768    2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9065    2.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1607    1.9573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7409    2.5659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4257    3.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5725    2.5449    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
 25 24  1  6  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 34 33  1  1  0  0  0
 24 34  1  0  0  0  0
 28 34  1  0  0  0  0
 26 35  1  6  0  0  0
 15 35  1  6  0  0  0
 26 36  1  0  0  0  0
 36 37  2  0  0  0  0
 38 36  1  6  0  0  0
 15 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 12 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C[C@H]1OC(C)(C)C2=C1C[C@]13CC[C@@]4(C)[C@@H]5[C@H]([C@H](C)C4=O)[C@H]4OC(=O)[C@@H](C)[C@H]4O[C@@]5(O1)C(=O)[C@@H]3[C@@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O10/c1-7-37-19(33)11-18-15-12-30-9-8-29(6)24-20(13(2)25(29)34)23-22(14(3)27(36)38-23)40-31(24,41-30)26(35)21(30)17(32)10-16(15)28(4,5)39-18/h13-14,17-18,20-24,32H,7-12H2,1-6H3/t13-,14-,17-,18+,20+,21-,22+,23+,24-,29-,30-,31-/m0/s1

> <INCHI_KEY>
MJYGKMGYFLJZNM-SMOIPZKWSA-N

> <FORMULA>
C31H40O10

> <MOLECULAR_WEIGHT>
572.651

> <EXACT_MASS>
572.262147488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
60.427734219944035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacos-16(20)-en-17-yl]acetate

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
2.776045367999999

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.374536647690945

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.559514073191323

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9735417932406465

> <JCHEM_POLAR_SURFACE_AREA>
134.66

> <JCHEM_REFRACTIVITY>
141.89639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl [(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacos-16(20)-en-17-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      20.996  -4.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.880  -3.198   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.493  -2.530   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      19.377  -0.995   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      20.649  -0.126   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      17.989  -0.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.873   1.209   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.047   2.205   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.463   3.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.941   4.062   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.187   5.145   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.927   3.514   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.563   2.017   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.139   1.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.660   2.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.768   0.424   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.735  -0.757   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.154  -0.579   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.715  -2.013   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.131  -1.763   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.488  -3.261   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.700  -1.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.387  -1.981   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.831   0.394   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.347   0.807   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.862   2.389   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.614   3.403   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.120   2.990   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.824   3.823   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.736   5.360   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.632   2.848   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.142   3.239   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.191   1.413   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.728   1.501   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.222   2.086   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.717   3.824   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.026   5.200   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.367   3.654   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.450   4.790   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.861   6.213   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.002   4.750   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   41                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35   38                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   34                                                  
CONECT   25   24   18   26                                                  
CONECT   26   25   27   35   36                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   24   28                                                  
CONECT   35   26   15                                                       
CONECT   36   26   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   15   39                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   12                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1,.0,.0,.0,.0,]hexacos-16(20)-en-17-yl]acetic acid	Generator

Chemical Formula

C₃₁H₄₀O₁₀

Average Mass

572.6510 Da

Monoisotopic Mass

572.26215 Da

IUPAC Name

ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacos-16(20)-en-17-yl]acetate

Traditional Name

ethyl [(1S,3R,4S,7R,8S,9S,11S,14S,17R,22S,23R,26S)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacos-16(20)-en-17-yl]acetate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C[C@H]1OC(C)(C)C2=C1C[C@]13CC[C@@]4(C)[C@@H]5[C@H]([C@H](C)C4=O)[C@H]4OC(=O)[C@@H](C)[C@H]4O[C@@]5(O1)C(=O)[C@@H]3[C@@H](O)C2

InChI Identifier

InChI=1S/C31H40O10/c1-7-37-19(33)11-18-15-12-30-9-8-29(6)24-20(13(2)25(29)34)23-22(14(3)27(36)38-23)40-31(24,41-30)26(35)21(30)17(32)10-16(15)28(4,5)39-18/h13-14,17-18,20-24,32H,7-12H2,1-6H3/t13-,14-,17-,18+,20+,21-,22+,23+,24-,29-,30-,31-/m0/s1

InChI Key

MJYGKMGYFLJZNM-SMOIPZKWSA-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
Schisandra rubriflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Furopyran
Ketal
Oxepane
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Pyran
Oxane
Dihydrofuran
Furan
Oxolane
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aldehyde
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.46	ALOGPS
logP	2.78	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.9 m³·mol⁻¹	ChemAxon
Polarizability	60.43 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

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

23624674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate (NP0160865)

MOL for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

3D MOL for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

3D SDF for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

3D-SDF for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

PDB for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

3D PDB for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

SMILES for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

INCHI for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

Structure for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)

3D Structure for NP0160865 (ethyl 2-[(1s,3r,4s,7r,8s,9s,11s,14s,17r,22s,23r,26s)-22-hydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl]acetate)