NP-MRD: Showing NP-Card for methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0228939)

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Record Information

Version

2.0

Created at

2022-09-06 08:47:43 UTC

Updated at

2022-09-06 08:47:43 UTC

NP-MRD ID

NP0228939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511572D          

 30 31  0  0  0  0            999 V2000
    6.8148    3.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251    2.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159    2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963    2.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458    0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8562    0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1470   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1830   -0.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726    0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285   -1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985    0.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -0.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    0.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    1.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9882    0.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6871    2.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675    2.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582    2.0605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571    3.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375    3.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    4.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    3.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    0.0251    0.0000 O   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  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  4  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
   -3.1771   -2.4394    2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868   -1.3949    2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.0881    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415   -0.0769    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0063    1.1268   -0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106    1.1967   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793    2.5042   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442    2.6951   -2.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569    3.6125   -1.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2676    4.8370   -2.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219    0.1007   -1.6048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2412    0.5648   -2.5741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2379   -0.4157   -0.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1129   -0.1205   -0.6406 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428    0.7266    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207    1.2603    1.0873 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597    1.0138   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206    1.9469    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615    0.4643   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3931    0.8054   -1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -1.9014   -0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8330   -2.6170   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360   -2.6406   -2.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126   -3.3205    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -4.2005    0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416   -2.8163    1.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -2.4393    1.0345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9055   -1.5908    2.1476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6547   -2.3025    3.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997   -1.6455    4.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -2.3740    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776   -3.4300    2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.0145    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548    0.7391    2.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -0.9610   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679   -0.1844    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6172    2.0110   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2003    5.4324   -2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    4.6759   -3.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    5.4062   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786   -0.7448   -2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    0.9304   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503    0.1726    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    2.4697    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197    2.7269    0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714    1.3640    1.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5109   -0.2269   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1605   -1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622    1.4772   -2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.2710   -0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2141   -2.2341   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -3.2008   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -2.1092   -2.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -3.3949    1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.6376    2.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -1.8489    5.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 28  1  0
 28 29  1  0
 29 30  1  0
 28 27  1  0
 27 26  1  0
 26 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  2  3
 22 21  1  0
 21 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 13 11  1  0
 11 12  1  0
 11  6  1  0
 21 27  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  5 37  1  0
  4 35  1  0
  4 36  1  0
  3 33  1  0
  3 34  1  0
  1 31  1  0
  1 32  1  0
 28 55  1  1
 30 56  1  0
 27 54  1  6
 23 52  1  0
 23 53  1  0
 21 51  1  6
 13 43  1  1
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 11 41  1  6
 12 42  1  0
M  END


  Mrv1533004241511572D          

 30 31  0  0  0  0            999 V2000
    6.8148    3.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251    2.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159    2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963    2.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458    0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8562    0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1470   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1830   -0.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726    0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285   -1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985    0.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -0.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    0.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    1.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9882    0.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6871    2.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675    2.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582    2.0605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571    3.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375    3.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    4.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    3.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    0.0251    0.0000 O   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  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  4  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CCCC(=C)C(OO)C2OC(=O)C(=C)C2C(OC(=O)C(C)=CC)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O9/c1-6-10(2)19(23)28-17-14-12(4)20(24)29-18(14)16(30-26)11(3)8-7-9-13(15(17)22)21(25)27-5/h6,9,14-18,22,26H,3-4,7-8H2,1-2,5H3

> <INCHI_KEY>
GEAVRACREUWZDP-UHFFFAOYSA-N

> <FORMULA>
C21H26O9

> <MOLECULAR_WEIGHT>
422.43

> <EXACT_MASS>
422.157682417

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.62842069496774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.7682313633333324

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.288119779010323

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.68880807590477

> <JCHEM_PKA_STRONGEST_BASIC>
-3.552603033923945

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
104.67989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3aH,4H,5H,8H,9H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.721   6.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.740   4.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.416   3.913   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.073   4.666   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.436   2.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.779   1.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.798   0.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.474  -0.706   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.675  -0.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.656   1.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.807  -0.740   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.826  -2.280   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.503  -3.066   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.464   0.013   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.005  -0.481   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.085   0.754   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.545   0.734   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.974   2.011   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.480   3.469   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.445   1.553   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.769   2.340   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.749   3.880   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.406   4.633   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.082   3.846   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.387   6.173   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.043   6.926   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.024   8.466   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.711   6.960   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.112   1.587   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.131   0.047   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   21    5   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,10H,11H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆O₉

Average Mass

422.4300 Da

Monoisotopic Mass

422.15768 Da

IUPAC Name

methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3aH,4H,5H,8H,9H,11H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CCCC(=C)C(OO)C2OC(=O)C(=C)C2C(OC(=O)C(C)=CC)C1O

InChI Identifier

InChI=1S/C21H26O9/c1-6-10(2)19(23)28-17-14-12(4)20(24)29-18(14)16(30-26)11(3)8-7-9-13(15(17)22)21(25)27-5/h6,9,14-18,22,26H,3-4,7-8H2,1-2,5H3

InChI Key

GEAVRACREUWZDP-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Hydroxy acid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Methyl ester
Secondary alcohol
Hydroperoxide
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Peroxol
Oxacycle
Alkyl hydroperoxide
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
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	2.07	ALOGPS
logP	2.77	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.68 m³·mol⁻¹	ChemAxon
Polarizability	41.63 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 methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0228939)

MOL for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0228939 (methyl 11-hydroperoxy-5-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)