NP-MRD: Showing NP-Card for (3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate (NP0291334)

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Record Information

Version

1.0

Created at

2022-09-09 22:23:04 UTC

Updated at

2022-09-09 22:23:04 UTC

NP-MRD ID

NP0291334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

Description

(3AR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate is found in Centaurea spinosa. Based on a literature review very few articles have been published on (3aR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200232D          

 31 32  0  0  1  0            999 V2000
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6239   -0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526   -1.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    2.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  6  0  0  0
  6 24  1  0  0  0  0
 18 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    3.4877   -1.5121   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -1.0448    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8342   -0.5833    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -0.1324    1.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7774   -0.5961   -0.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278   -0.1692   -0.0691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785    1.0924   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8969    0.9019   -1.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4077    0.4241   -3.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850    1.1084   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    0.8702   -2.8870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698    1.5801   -0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3598    0.4916    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6500    0.6081    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.7206    2.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458    2.9800    2.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7252   -0.2697    1.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3181   -1.3677    1.1810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2683   -2.3415    0.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676   -3.2781    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249   -4.5071   -0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402   -2.5821   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -3.1755   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051   -1.1621   -0.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2283   -0.9857    1.2748 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4099   -1.5177    0.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637    0.4217    1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9060    1.3287    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0597    1.3393    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4190    2.3797   -0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9034    0.4343    0.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362   -1.5622   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4660   -1.8482   -1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837    0.1798    1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.4466   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004    1.9199   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -0.6769   -3.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527    0.7570   -4.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    0.8569   -3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619   -0.0665   -3.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058    2.2323   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.2918   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4282   -0.5080   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4460    0.7336    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3447    1.6507    3.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0444    1.5696    2.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    3.6185    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.1251    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -1.9919    1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -2.6985   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037   -4.2773   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3139   -0.9706   -0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -1.5658    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2422   -2.4709    0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.8038    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2857    0.3196    2.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6037    1.9080   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171    3.1096   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3493    2.9082   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 31  2  0
 29 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  1  0
 25  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  3
 22 24  1  0
 24  6  1  0
 24 18  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
 27 55  1  0
 27 56  1  0
 25 53  1  1
 26 54  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  1
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  1
 23 50  1  0
 23 51  1  0
 24 52  1  6
M  END


  Mrv1652309102200232D          

 31 32  0  0  1  0            999 V2000
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6239   -0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526   -1.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    2.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  6  0  0  0
  6 24  1  0  0  0  0
 18 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H](O)C(=C)C(=O)O[C@H]1C\C(C)=C(O)/CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O9/c1-11-7-18(30-21(27)12(2)17(26)10-29-14(4)24)20-13(3)22(28)31-19(20)8-15(9-23)5-6-16(11)25/h8,17-20,23,25-26H,2-3,5-7,9-10H2,1,4H3/b15-8-,16-11+/t17-,18-,19+,20+/m0/s1

> <INCHI_KEY>
ICZAZMYXLQSBDI-BXXUSGOYSA-N

> <FORMULA>
C22H28O9

> <MOLECULAR_WEIGHT>
436.457

> <EXACT_MASS>
436.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.80903862382239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

> <JCHEM_LOGP>
0.7198008826666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.524374241756302

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.627898953981983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.734830363625427

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
110.38309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.165  -1.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.965  -3.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000  -6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.654   2.276   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.185   2.437   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.955   3.771   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.812   1.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.318   0.710   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    6   18                                                  
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoic acid	Generator

Chemical Formula

C₂₂H₂₈O₉

Average Mass

436.4570 Da

Monoisotopic Mass

436.17333 Da

IUPAC Name

(3aR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

Traditional Name

(3aR,4S,11aR)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H](O)C(=C)C(=O)O[C@H]1C\C(C)=C(O)/CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C22H28O9/c1-11-7-18(30-21(27)12(2)17(26)10-29-14(4)24)20-13(3)22(28)31-19(20)8-15(9-23)5-6-16(11)25/h8,17-20,23,25-26H,2-3,5-7,9-10H2,1,4H3/b15-8-,16-11+/t17-,18-,19+,20+/m0/s1

InChI Key

ICZAZMYXLQSBDI-BXXUSGOYSA-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
Centaurea spinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Enol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Primary alcohol
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	0.72	ChemAxon
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.38 m³·mol⁻¹	ChemAxon
Polarizability	43.81 Å³	ChemAxon
Number of Rings	2	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

23339266

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163194225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate (NP0291334)

MOL for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

3D MOL for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

3D SDF for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

3D-SDF for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

PDB for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

3D PDB for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

SMILES for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

INCHI for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

Structure for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)

3D Structure for NP0291334 ((3ar,4s,11ar)-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate)