NP-MRD: Showing NP-Card for Monomethyl ester of 9-hydroxyhexylitaconic acid (NP0043924)

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Record Information

Version

1.0

Created at

2021-06-22 17:29:26 UTC

Updated at

2021-06-22 17:29:26 UTC

NP-MRD ID

NP0043924

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monomethyl ester of 9-hydroxyhexylitaconic acid

Description

CHEMBL458698 belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Monomethyl ester of 9-hydroxyhexylitaconic acid is found in Apiospora montagnei. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CHEMBL458698 (PMID: 15217297) (PMID: 27466641) (PMID: 27253005) (PMID: 26389468).

Structure

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

NP0043924
     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    3.2620    1.2775    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    1.5450    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449    2.9506    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801    3.8333    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027    3.3923   -0.8813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8341    0.4664   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520    0.5409   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752    0.4507    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    0.5295    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.5812   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225   -0.3728   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -1.4276   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4294   -0.4140    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -0.8877   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5433   -1.7840    0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -1.2452   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -2.5174    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    2.0609    1.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.2640    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    3.7222   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535    0.6275   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    1.4714   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3471   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -0.4358    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    1.3341    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    1.5061    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.4949    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855   -1.5516    0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -0.5531   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.6137   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6285   -1.0455   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -1.5836   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005   -2.4011   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668   -1.3120    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -2.6259    1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101   -2.7014   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858   -3.2940   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END


  Mrv1652306222119292D          

 17 16  0  0  0  0            999 V2000
    8.3033    2.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632    2.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9530    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    3.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4129    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0627    1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0043924

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(CCCCC(C)O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O5/c1-8(13)6-4-5-7-10(12(16)17-3)9(2)11(14)15/h8,10,13H,2,4-7H2,1,3H3,(H,14,15)

> <INCHI_KEY>
QSAIBULZNVPLAJ-UHFFFAOYSA-N

> <FORMULA>
C12H20O5

> <MOLECULAR_WEIGHT>
244.287

> <EXACT_MASS>
244.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.213685617470787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3-(methyl carboxy)-2-methylidenenonanoic acid

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.499876084333334

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.683060942941832

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5712144753378405

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6252280552341491

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
62.010000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3-(methyl carboxy)-2-methylidenenonanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043924
     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    3.2620    1.2775    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    1.5450    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449    2.9506    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801    3.8333    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027    3.3923   -0.8813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8341    0.4664   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520    0.5409   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752    0.4507    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    0.5295    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.5812   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225   -0.3728   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -1.4276   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4294   -0.4140    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -0.8877   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5433   -1.7840    0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -1.2452   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -2.5174    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    2.0609    1.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.2640    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    3.7222   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535    0.6275   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    1.4714   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3471   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -0.4358    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    1.3341    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    1.5061    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.4949    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855   -1.5516    0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -0.5531   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.6137   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6285   -1.0455   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -1.5836   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005   -2.4011   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668   -1.3120    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -2.6259    1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101   -2.7014   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858   -3.2940   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
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      15.499   5.117   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.491   3.953   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.979   4.244   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.475   5.699   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.971   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.459   3.371   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.450   2.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.938   2.498   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.418   1.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.410   0.461   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.914   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.475   1.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.995   2.498   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.491  -0.121   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   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    NP0043924
HETATM    1  C1  UNL     1       3.262   1.278   1.367  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.439   1.545   0.378  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.145   2.951   0.122  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.680   3.833   0.848  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.303   3.392  -0.881  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.834   0.466  -0.462  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.352   0.541  -0.580  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.375   0.451   0.730  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.864   0.530   0.569  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.414  -0.581  -0.295  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.923  -0.373  -0.367  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.595  -1.428  -1.209  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.429  -0.414   0.926  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.303  -0.888  -0.051  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.543  -1.784   0.399  1.00  0.00           O  
HETATM   16  O5  UNL     1       3.651  -1.245  -0.148  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.123  -2.517   0.233  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.688   2.061   1.947  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.504   0.264   1.593  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.716   3.722  -1.746  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.253   0.628  -1.490  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.068   1.471  -1.084  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.049  -0.347  -1.215  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.106  -0.436   1.336  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.081   1.334   1.362  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.138   1.506   0.124  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.336   0.495   1.572  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.185  -1.552   0.167  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.033  -0.553  -1.315  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.137   0.614  -0.810  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.629  -1.045  -1.424  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.072  -1.584  -2.171  1.00  0.00           H  
HETATM   33  H16 UNL     1      -4.701  -2.401  -0.670  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.567  -1.312   1.276  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.171  -2.626   1.339  1.00  0.00           H  
HETATM   36  H19 UNL     1       5.110  -2.701  -0.237  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.386  -3.294  -0.120  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    6
CONECT    3    4    4    5
CONECT    5   20
CONECT    6    7   14   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   13   30
CONECT   12   31   32   33
CONECT   13   34
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   35   36   37
END

NP0043924
     RDKit          3D

37 36  0  0  0  0  0  0  0  0999 V2000
    3.2620    1.2775    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    1.5450    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449    2.9506    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801    3.8333    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027    3.3923   -0.8813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8341    0.4664   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520    0.5409   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752    0.4507    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    0.5295    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.5812   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225   -0.3728   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -1.4276   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4294   -0.4140    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031   -0.8877   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5433   -1.7840    0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -1.2452   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -2.5174    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    2.0609    1.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.2640    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    3.7222   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535    0.6275   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    1.4714   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.3471   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -0.4358    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    1.3341    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    1.5061    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.4949    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1855   -1.5516    0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -0.5531   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.6137   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6285   -1.0455   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -1.5836   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005   -2.4011   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668   -1.3120    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -2.6259    1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101   -2.7014   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858   -3.2940   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
9-Hydroxyhexylitaconate	Generator
8-Hydroxy-3-(methoxycarbonyl)-2-methylidenenonanoate	Generator

Chemical Formula

C₁₂H₂₀O₅

Average Mass

244.2870 Da

Monoisotopic Mass

244.13107 Da

IUPAC Name

8-hydroxy-3-(methyl carboxy)-2-methylidenenonanoic acid

Traditional Name

8-hydroxy-3-(methyl carboxy)-2-methylidenenonanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C(CCCCC(C)O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C12H20O5/c1-8(13)6-4-5-7-10(12(16)17-3)9(2)11(14)15/h8,10,13H,2,4-7H2,1,3H3,(H,14,15)

InChI Key

QSAIBULZNVPLAJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone, 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
Arthrinium arundinis	Linigton's dataset	15217297

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Fatty acid ester
Methyl-branched fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Unsaturated fatty acid
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.72	ALOGPS
logP	1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	62.01 m³·mol⁻¹	ChemAxon
Polarizability	26.21 Å³	ChemAxon
Number of Rings	0	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

9486077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11311109

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Klemke C, Kehraus S, Wright AD, Konig GM: New secondary metabolites from the marine endophytic fungus Apiospora montagnei. J Nat Prod. 2004 Jun;67(6):1058-63. doi: 10.1021/np034061x. [PubMed:15217297 ]
Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]

Showing NP-Card for Monomethyl ester of 9-hydroxyhexylitaconic acid (NP0043924)

MOL for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

3D MOL for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

3D SDF for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

3D-SDF for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

PDB for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

3D PDB for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

SMILES for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

INCHI for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

Structure for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)

3D Structure for NP0043924 (Monomethyl ester of 9-hydroxyhexylitaconic acid)