NP-MRD: Showing NP-Card for 17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate (NP0275280)

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Record Information

Version

2.0

Created at

2022-09-08 22:58:33 UTC

Updated at

2022-09-08 22:58:33 UTC

NP-MRD ID

NP0275280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate

Description

17-[(Acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]Henicosan-6-yl 2-methylbut-2-enoate 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. 17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate is found in Swietenia mahagoni. 17-[(Acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]Henicosan-6-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514272D          

 57 64  0  0  0  0            999 V2000
    5.0186   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2576   -1.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -0.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8093    0.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919   -0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791    1.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9972    1.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138    1.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068    1.9605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5724    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881    0.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829    1.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    0.8883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067    1.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3303    0.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    2.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    2.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699    2.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110    3.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942    4.1637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    4.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4100    4.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351    1.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579    1.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541    0.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1535    0.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4227   -0.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    2.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781    3.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    3.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    4.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190    3.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761    2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405    1.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570    1.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6973    2.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9674    2.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    2.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    1.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152    2.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288    3.4683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069    3.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792    4.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    4.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7661    5.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    3.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899    2.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    2.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    2.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1790    2.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3478    1.8661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939    3.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5777    2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1926    3.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6251    4.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 39  1  0  0  0  0
 19 40  1  0  0  0  0
 14 40  1  0  0  0  0
 40 41  1  0  0  0  0
 16 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 44 48  1  0  0  0  0
 48 49  1  0  0  0  0
 10 49  1  0  0  0  0
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
  7 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  4  0  0  0
 54 57  1  0  0  0  0
M  END

     RDKit          3D

109116  0  0  0  0  0  0  0  0999 V2000
    4.4802   -4.8118    1.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5097   -4.2044    2.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9109   -3.0893    2.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426   -2.5208    2.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539   -2.3769    0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656   -2.8329   -0.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5166   -1.1673    0.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -0.5450   -0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3795    0.8797   -0.5109 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7271    0.8501    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2503    1.3237   -1.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119    1.1858   -1.9620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3331    1.6287   -3.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664    2.0475   -0.7678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3045    3.4583   -1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449    1.7247    0.2059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8483    2.7124    1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    3.7946    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823    4.0760   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289    4.6637    1.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9747    5.7449    1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1439    1.7188   -0.3846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9827    2.6149   -1.1214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7551    1.8391   -1.9416 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.6970    1.2412   -1.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0399   -1.1774   -1.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4488    0.7367    3.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    0.7608    5.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540    0.4001    5.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345    0.1468    4.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9655    1.7574    1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187    2.0751    1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4960    3.5022    1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    0.4109   -0.8800 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.7054    0.7273    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3903    1.6362   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    0.4894   -2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6088    2.2877   -2.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3901    3.5405   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209    3.6440   -2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161514272D          

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M  END
> <DATABASE_ID>
NP0275280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2(C)CC3(O)C1(C)C14OC5(C)OC(CC(=O)OC)(C1(O5)C1OC(C)(OC)OC31C2OC(=O)C(C)=CC)C(C)(CC4O)C(OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C40H52O17/c1-12-20(2)28(45)52-29-31(4)19-36(46)33(6,23(31)15-25(43)47-9)39-24(42)16-32(5,27(51-21(3)41)22-13-14-50-18-22)37(17-26(44)48-10)40(39,57-35(8,54-37)56-39)30-38(29,36)55-34(7,49-11)53-30/h12-14,18,23-24,27,29-30,42,46H,15-17,19H2,1-11H3

> <INCHI_KEY>
GSACHNDPLCWILD-UHFFFAOYSA-N

> <FORMULA>
C40H52O17

> <MOLECULAR_WEIGHT>
804.839

> <EXACT_MASS>
804.320450214

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
80.97343553521331

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
3.2940250543333316

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.905472301321037

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.985584304328011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.843540820487676

> <JCHEM_POLAR_SURFACE_AREA>
214.17999999999998

> <JCHEM_REFRACTIVITY>
188.95060000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       9.368  -3.035   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.948  -2.440   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.752  -0.913   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.977   0.020   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.332  -0.318   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.136   1.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.241   2.415   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.700   1.922   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.461   3.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.626   3.340   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.119   3.660   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.802   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.271   0.627   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.141   2.289   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.660   1.658   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.573   2.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.617   1.587   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.260   4.084   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.095   4.510   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.371   5.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.261   6.909   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.536   7.772   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.875   7.582   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.765   9.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.066   3.088   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.415   2.346   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.474   1.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.153   0.942   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.656  -0.514   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.051   4.272   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.519   5.717   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.505   6.900   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.973   8.346   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.022   6.639   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.569   4.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.249   2.628   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.773   2.848   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.035   4.366   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.672   5.084   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.696   3.916   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.779   3.390   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.762   5.013   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.227   6.474   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.493   7.331   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.508   8.515   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.573   8.428   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       5.163   9.913   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.709   6.351   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.395   4.785   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.057   4.445   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.204   5.472   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       9.667   4.991   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       9.983   3.483   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      10.815   6.017   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      12.278   5.537   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      13.426   6.563   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      10.500   7.525   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9   50                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   49                                             
CONECT   11   10                                                            
CONECT   12   10    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   28   40                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18   41                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   25   40                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   19   26   27   30                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   14   29                                                  
CONECT   29   28                                                            
CONECT   30   25   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   35                                                       
CONECT   40   19   14   41   42                                             
CONECT   41   40   16                                                       
CONECT   42   40   43   49                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46   48                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   44   49                                                       
CONECT   49   48   10   42   50                                             
CONECT   50   49    7   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   57                                                  
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57   54                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  128    0
END

View in JSmol

Synonyms

Value	Source
17-[(Acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1,.0,.0,.0,.0,]henicosan-6-yl 2-methylbut-2-enoic acid	Generator
17-[(Acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₄₀H₅₂O₁₇

Average Mass

804.8390 Da

Monoisotopic Mass

804.32045 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)CC3(O)C1(C)C14OC5(C)OC(CC(=O)OC)(C1(O5)C1OC(C)(OC)OC31C2OC(=O)C(C)=CC)C(C)(CC4O)C(OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C40H52O17/c1-12-20(2)28(45)52-29-31(4)19-36(46)33(6,23(31)15-25(43)47-9)39-24(42)16-32(5,27(51-21(3)41)22-13-14-50-18-22)37(17-26(44)48-10)40(39,57-35(8,54-37)56-39)30-38(29,36)55-34(7,49-11)53-30/h12-14,18,23-24,27,29-30,42,46H,15-17,19H2,1-11H3

InChI Key

GSACHNDPLCWILD-UHFFFAOYSA-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
Swietenia mahagoni	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
Diterpenoid
Tetracarboxylic acid or derivatives
Carboxylic acid orthoester
Fatty acid ester
Ortho ester
Meta-dioxane
Meta-dioxolane
Cyclic alcohol
Heteroaromatic compound
Furan
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Orthocarboxylic acid derivative
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.36	ALOGPS
logP	3.29	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	214.18 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	188.95 m³·mol⁻¹	ChemAxon
Polarizability	80.97 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

85368805

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate (NP0275280)

MOL for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

3D MOL for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

3D SDF for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

3D-SDF for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

PDB for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

3D PDB for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

SMILES for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

INCHI for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

Structure for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)

3D Structure for NP0275280 (17-[(acetyloxy)(furan-3-yl)methyl]-3,19-dihydroxy-9-methoxy-16,21-bis(2-methoxy-2-oxoethyl)-2,5,9,14,17-pentamethyl-8,10,13,15,20-pentaoxaheptacyclo[12.5.1.1²,⁵.0¹,¹².0³,⁷.0⁷,¹¹.0¹²,¹⁶]henicosan-6-yl 2-methylbut-2-enoate)