NP-MRD: Showing NP-Card for 10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate (NP0185487)

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Record Information

Version

2.0

Created at

2022-09-04 00:54:46 UTC

Updated at

2022-09-04 00:54:46 UTC

NP-MRD ID

NP0185487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate

Description

10-[(Acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate 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. 10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate is found in Dicoma anomala. 10-[(Acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191515082D          

 30 31  0  0  0  0            999 V2000
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 C   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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -3.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -3.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448   -3.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378   -2.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -2.0906   -2.0103   -2.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9561   -1.9306   -1.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -3.0577   -1.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989   -4.1936   -1.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186   -2.6568   -1.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549   -1.2619   -1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2450   -0.5968   -1.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    0.0667   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5236   -0.6801   -0.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958    0.0677    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6136   -0.4728    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779    0.2751    1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8789   -1.6324    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    1.2761   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8258    2.1059   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996    2.3213    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    1.0742    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120    0.9399    2.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010    2.0049    3.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    0.0983    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    0.0693   -0.4279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1125   -0.4242   -0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2552    0.2897   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1517    1.4677   -0.9096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228   -0.2988   -0.2478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7347   -0.9009    1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7017    0.6762   -0.5872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0265   -0.0451   -0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937    1.0911   -1.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588   -0.7300   -1.5187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5245   -2.9838   -2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -1.1275   -2.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -1.1369    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.1616   -2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -1.4163   -2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -1.5888   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432   -1.0307   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2466   -0.4802    1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2207    0.9490    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0527    0.9013    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    1.7228    0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    1.8255   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    3.1335   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010    2.6951    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3920    3.1289    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.0410    2.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    1.0975    2.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    2.5378    2.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974   -0.7833    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    1.1216   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038   -1.1451   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -0.6723    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.4909    1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681   -2.0237    1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6887    1.5678    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7275    0.2685   -1.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8995   -1.1517   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4854    0.0845    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5732    2.0750   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -0.1304   -2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 17  2  0
 17 18  1  0
 18 19  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 30  1  0
 30 21  1  0
 30  6  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 27 55  1  1
 29 59  1  0
 25 51  1  6
 26 52  1  0
 26 53  1  0
 26 54  1  0
 21 50  1  6
 20 49  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 16 44  1  0
 16 45  1  0
 15 42  1  0
 15 43  1  0
 14 41  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
  7 34  1  0
  7 35  1  0
  6 33  1  1
  1 31  1  0
  1 32  1  0
 30 60  1  6
M  END


  Mrv1533004191515082D          

 30 31  0  0  0  0            999 V2000
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 C   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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -3.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -3.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448   -3.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378   -2.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(C)C(=O)OC1C=C(CO)CCC=C(COC(C)=O)CC2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O8/c1-12(14(3)24)21(26)29-18-8-16(10-23)6-5-7-17(11-28-15(4)25)9-19-20(18)13(2)22(27)30-19/h7-8,12,14,18-20,23-24H,2,5-6,9-11H2,1,3-4H3

> <INCHI_KEY>
ZIBLLTNJLPGGIB-UHFFFAOYSA-N

> <FORMULA>
C22H30O8

> <MOLECULAR_WEIGHT>
422.474

> <EXACT_MASS>
422.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.725225546393816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.1710393473333327

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.39197037654947

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.781814265548597

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7347865087301892

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
108.76439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.348  -6.896   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.817  -7.057   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.047  -8.391   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.190  -5.650   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.684  -5.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    9   24                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
10-[(Acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3ah,4H,7H,8H,11H,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate

Traditional Name

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(O)C(C)C(=O)OC1C=C(CO)CCC=C(COC(C)=O)CC2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C22H30O8/c1-12(14(3)24)21(26)29-18-8-16(10-23)6-5-7-17(11-28-15(4)25)9-19-20(18)13(2)22(27)30-19/h7-8,12,14,18-20,23-24H,2,5-6,9-11H2,1,3-4H3

InChI Key

ZIBLLTNJLPGGIB-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
Dicoma anomala	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
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	1.55	ALOGPS
logP	1.17	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.76 m³·mol⁻¹	ChemAxon
Polarizability	43.73 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate (NP0185487)

MOL for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

3D MOL for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

3D SDF for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

3D-SDF for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

PDB for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

3D PDB for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

SMILES for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

INCHI for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

Structure for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)

3D Structure for NP0185487 (10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate)