NP-MRD: Showing NP-Card for Fischeriolide A (NP0043873)

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Record Information

Version

2.0

Created at

2021-06-22 17:26:55 UTC

Updated at

2021-06-22 17:26:55 UTC

NP-MRD ID

NP0043873

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fischeriolide A

Description

Fischeriolide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Fischeriolide A is found in Euphorbia fischeriana. Based on a literature review very few articles have been published on Fischeriolide A.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043873
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2456    1.1956   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -0.0548   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.2843    0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    0.5429    1.2805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0010    1.8276    1.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    0.5909    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    1.5790    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286    1.8079    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.6880   -0.1761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412    0.6361   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6459    0.4234    1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    1.9939   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -0.3830   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.7287   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.5998   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.6131    0.0742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9863   -1.1373    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.3561   -0.2874 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3537   -1.6132   -0.4970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3069   -1.9407   -1.8734 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8055   -1.6009   -0.1240 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6871   -2.0681   -1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7199   -1.1747   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -1.2659   -1.9751 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6538    1.2466    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.1024   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1220    1.1523   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    0.0112    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270    2.3821    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    2.3005    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605    2.7570    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.9821    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    0.9736   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    0.5221    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173    1.1196    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.5989    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345    2.7039    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160    2.4473   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    1.9119   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -0.5048   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3177    0.0369   -2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549   -2.1377   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -2.3588   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -1.1489   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -2.6017   -0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.9410    1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724   -1.6171    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594   -0.3518    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297    0.1795   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -2.5064   -0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096   -1.2494   -2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -2.2773    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23  2  1  0
 21  3  1  0
 18  6  1  0
 16  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  1
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  6
 19 50  1  1
 20 51  1  0
 21 52  1  1
M  END


  Mrv1652306222119262D          

 24 27  0  0  1  0            999 V2000
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    1.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0092    1.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -0.1062    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  1  0  0  0
  7 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  6  0  0  0
  5 21  1  6  0  0  0
  4 22  1  6  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0043873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@H](OC1=O)[C@H](O)[C@@H]1C(=CC[C@@H]3C(C)(C)CCC[C@@]13C)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-10-13-15(21)11-6-7-12-19(2,3)8-5-9-20(12,4)14(11)16(22)17(13)24-18(10)23/h6,12,14-17,21-22H,5,7-9H2,1-4H3/t12-,14+,15+,16-,17+,20-/m1/s1

> <INCHI_KEY>
WZDKXCLDLXYMLQ-ULBMWCGFSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.07536536799419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,7R,11S,16S,17R)-11,17-dihydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-9,12-dien-14-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.504047142666666

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.41365424106062

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.00498990627863

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2989684195631153

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
91.61689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,11S,16S,17R)-11,17-dihydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-9,12-dien-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043873
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2456    1.1956   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -0.0548   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.2843    0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    0.5429    1.2805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0010    1.8276    1.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    0.5909    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    1.5790    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286    1.8079    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.6880   -0.1761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412    0.6361   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6459    0.4234    1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    1.9939   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -0.3830   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.7287   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.5998   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.6131    0.0742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9863   -1.1373    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.3561   -0.2874 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3537   -1.6132   -0.4970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3069   -1.9407   -1.8734 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8055   -1.6009   -0.1240 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6871   -2.0681   -1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7199   -1.1747   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -1.2659   -1.9751 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6538    1.2466    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.1024   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1220    1.1523   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    0.0112    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270    2.3821    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    2.3005    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605    2.7570    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.9821    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    0.9736   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    0.5221    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173    1.1196    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.5989    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345    2.7039    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160    2.4473   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    1.9119   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -0.5048   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3177    0.0369   -2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549   -2.1377   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -2.3588   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -1.1489   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -2.6017   -0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.9410    1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724   -1.6171    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594   -0.3518    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297    0.1795   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -2.5064   -0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096   -1.2494   -2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -2.2773    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23  2  1  0
 21  3  1  0
 18  6  1  0
 16  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  1
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  6
 19 50  1  1
 20 51  1  0
 21 52  1  1
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.896   3.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.380   3.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.088   2.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.017   3.453   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.842  -0.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.835  -1.314   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.813  -0.198   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    6   12   18                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11                                                            
CONECT   19    7    3   20                                                  
CONECT   20   19                                                            
CONECT   21    5                                                            
CONECT   22    4   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    NP0043873
HETATM    1  C1  UNL     1       5.246   1.196  -0.182  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.422  -0.055  -0.348  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.293  -0.284   0.281  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.514   0.543   1.280  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.001   1.828   1.366  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.132   0.591   0.699  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.354   1.579   1.129  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.029   1.808   0.689  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.558   0.688  -0.176  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.041   0.636  -0.134  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.646   0.423   1.201  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.543   1.994  -0.653  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.533  -0.383  -1.165  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.880  -1.729  -0.942  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.366  -1.600  -0.969  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.863  -0.613   0.074  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.986  -1.137   1.460  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.614  -0.356  -0.287  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.354  -1.613  -0.497  1.00  0.00           C  
HETATM   20  O2  UNL     1       1.307  -1.941  -1.873  1.00  0.00           O  
HETATM   21  C19 UNL     1       2.805  -1.601  -0.124  1.00  0.00           C  
HETATM   22  O3  UNL     1       3.687  -2.068  -1.069  1.00  0.00           O  
HETATM   23  C20 UNL     1       4.720  -1.175  -1.228  1.00  0.00           C  
HETATM   24  O4  UNL     1       5.740  -1.266  -1.975  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.654   1.247   0.866  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.664   2.102  -0.360  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.122   1.152  -0.852  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.464   0.011   2.231  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.527   2.382   0.697  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.741   2.300   1.872  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.060   2.757   0.115  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.646   1.982   1.594  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.278   0.974  -1.236  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.990   0.522   2.061  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.517   1.120   1.383  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.126  -0.599   1.198  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.634   2.704   0.216  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.816   2.447  -1.350  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.538   1.912  -1.090  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.617  -0.505  -1.014  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.318   0.037  -2.169  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.255  -2.138  -0.004  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.149  -2.359  -1.814  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.112  -1.149  -1.964  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.952  -2.602  -0.865  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.231  -1.941   1.605  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.972  -1.617   1.602  1.00  0.00           H  
HETATM   48  H24 UNL     1      -0.759  -0.352   2.179  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.530   0.179  -1.285  1.00  0.00           H  
HETATM   50  H26 UNL     1       0.888  -2.506  -0.008  1.00  0.00           H  
HETATM   51  H27 UNL     1       1.710  -1.249  -2.425  1.00  0.00           H  
HETATM   52  H28 UNL     1       2.931  -2.277   0.786  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   23
CONECT    3    4   21
CONECT    4    5    6   28
CONECT    5   29
CONECT    6    7    7   18
CONECT    7    8   30
CONECT    8    9   31   32
CONECT    9   10   16   33
CONECT   10   11   12   13
CONECT   11   34   35   36
CONECT   12   37   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   18
CONECT   17   46   47   48
CONECT   18   19   49
CONECT   19   20   21   50
CONECT   20   51
CONECT   21   22   52
CONECT   22   23
CONECT   23   24   24
END

NP0043873
     RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
    5.2456    1.1956   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -0.0548   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.2843    0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    0.5429    1.2805 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0010    1.8276    1.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    0.5909    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    1.5790    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286    1.8079    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.6880   -0.1761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412    0.6361   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6459    0.4234    1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    1.9939   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -0.3830   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.7287   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.5998   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.6131    0.0742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9863   -1.1373    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.3561   -0.2874 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3537   -1.6132   -0.4970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3069   -1.9407   -1.8734 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8055   -1.6009   -0.1240 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6871   -2.0681   -1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7199   -1.1747   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396   -1.2659   -1.9751 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6538    1.2466    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.1024   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1220    1.1523   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    0.0112    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270    2.3821    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    2.3005    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605    2.7570    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.9821    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    0.9736   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    0.5221    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173    1.1196    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1261   -0.5989    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345    2.7039    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160    2.4473   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    1.9119   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -0.5048   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3177    0.0369   -2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549   -2.1377   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -2.3588   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -1.1489   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -2.6017   -0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.9410    1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724   -1.6171    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594   -0.3518    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297    0.1795   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -2.5064   -0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096   -1.2494   -2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -2.2773    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23  2  1  0
 21  3  1  0
 18  6  1  0
 16  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  1
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  6
 19 50  1  1
 20 51  1  0
 21 52  1  1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1S,2R,7R,11S,16S,17R)-11,17-dihydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-9,12-dien-14-one

Traditional Name

(1S,2R,7R,11S,16S,17R)-11,17-dihydroxy-2,6,6,13-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-9,12-dien-14-one

CAS Registry Number

Not Available

SMILES

CC1=C2[C@H](OC1=O)[C@H](O)[C@@H]1C(=CC[C@@H]3C(C)(C)CCC[C@@]13C)[C@@H]2O

InChI Identifier

InChI=1S/C20H28O4/c1-10-13-15(21)11-6-7-12-19(2,3)8-5-9-20(12,4)14(11)16(22)17(13)24-18(10)23/h6,12,14-17,21-22H,5,7-9H2,1-4H3/t12-,14+,15+,16-,17+,20-/m1/s1

InChI Key

WZDKXCLDLXYMLQ-ULBMWCGFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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
Euphorbia fischeriana	Linigton's dataset	26702644

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Abietane diterpenoid
Diterpenoid
Naphthofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	2.71	ALOGPS
logP	2.5	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.62 m³·mol⁻¹	ChemAxon
Polarizability	37.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

58920824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127041907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Fischeriolide A (NP0043873)

MOL for NP0043873 (Fischeriolide A)

3D MOL for NP0043873 (Fischeriolide A)

3D SDF for NP0043873 (Fischeriolide A)

3D-SDF for NP0043873 (Fischeriolide A)

PDB for NP0043873 (Fischeriolide A)

3D PDB for NP0043873 (Fischeriolide A)

SMILES for NP0043873 (Fischeriolide A)

INCHI for NP0043873 (Fischeriolide A)

Structure for NP0043873 (Fischeriolide A)

3D Structure for NP0043873 (Fischeriolide A)