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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:29:59 UTC

Update Date

2022-03-07 02:54:53 UTC

HMDB ID

HMDB0036363

Secondary Accession Numbers

HMDB36363

Metabolite Identification

Common Name

4-Deoxy-6-hydroxysquamotacin

Description

4-Deoxy-6-hydroxysquamotacin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a small amount of articles have been published on 4-Deoxy-6-hydroxysquamotacin.

Structure

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


  Mrv0541 02241211242D          

 44 46  0  0  0  0            999 V2000
   -4.9909    0.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9909   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100   -0.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274    0.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    0.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9909   -1.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9909   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100   -2.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -2.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5454    1.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    2.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684    3.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494    2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425    1.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706    3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9221   -3.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6545   -3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    2.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9221    2.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882    2.8426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 11 41  1  0  0  0  0
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

HMDB0036363
     RDKit          3D
4-Deoxy-6-hydroxysquamotacin
110112  0  0  0  0  0  0  0  0999 V2000
  -12.6378   -0.2404    2.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5558    0.0442    1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6461   -1.2441    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6102   -1.1333   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2534   -0.4813   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1766   -0.3632   -2.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9969    0.2287   -3.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6289    1.6306   -3.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2226    2.1837   -1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9644    1.7819   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6951    0.3693   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    0.1595   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    0.6499   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    2.0389   -0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9610    0.3279    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    1.0561    1.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4447   -1.2892    1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -0.3916    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -1.1886    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5302   -0.3106   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1583   -0.1050    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3484    0.6881    1.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    0.7765   -0.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241211242D          

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M  END
> <DATABASE_ID>
HMDB0036363

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCC(O)CCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-16-13-12-14-19-30(38)20-17-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3

> <INCHI_KEY>
WWLPFTIHLMRECR-UHFFFAOYSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
78.83632293025025

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(4,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
6.90

> <JCHEM_LOGP>
8.682191933333334

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.432265089232693

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.873469088840213

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2442604996733237

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
176.3966

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036363
     RDKit          3D
4-Deoxy-6-hydroxysquamotacin
110112  0  0  0  0  0  0  0  0999 V2000
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    8.0192   -0.0325    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -2.0261    2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0391    1.2545    1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4015    1.1261   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6300   -0.6323    1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0039   -0.8427   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2121    1.7372    0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6481    1.4002   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5432    0.7725   -2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2465   -1.2823   -2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5519    0.4832   -3.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1076    1.5760   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3417    0.2250   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
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 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
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 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 22 43  1  0
 18 44  1  0
 44 15  1  0
 43 19  1  0
 41 36  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
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  3 50  1  0
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  8 60  1  0
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 33100  1  0
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 39110  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.316   0.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.316  -0.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.859  -1.025   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.958   0.219   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.859   1.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.316  -3.014   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.316  -4.554   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.859  -5.029   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.958  -3.784   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.859  -2.547   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.859   2.996   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.688   3.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.351   2.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.014   3.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.323   2.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.658   3.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.995   2.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.332   3.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.669   2.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.999   3.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.485   3.366   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.316   4.654   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.341   5.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.999   5.283   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.039   1.931   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.718   7.339   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.859  -6.569   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.522  -7.339   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.184  -6.569   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.188  -7.339   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.847  -7.339   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.510  -6.569   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.180  -7.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.156  -6.569   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.486  -7.339   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.823  -6.569   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.152  -7.339   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.490  -6.569   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.822  -7.339   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.156  -6.569   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.522   3.766   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.184   2.996   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -9.188   3.766   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.658   5.306   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4   11                                                  
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    3    6    9                                                  
CONECT   11    5   41   43                                                  
CONECT   12   13   42                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   44                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   20   23                                                       
CONECT   25   21                                                            
CONECT   26   23                                                            
CONECT   27    8   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   31                                                       
CONECT   30   27                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   11   42                                                       
CONECT   42   12   41                                                       
CONECT   43   11                                                            
CONECT   44   16                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

COMPND    HMDB0036363
HETATM    1  C1  UNL     1     -12.638  -0.240   2.955  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.556   0.044   1.450  1.00  0.00           C  
HETATM    3  C3  UNL     1     -12.646  -1.244   0.713  1.00  0.00           C  
HETATM    4  C4  UNL     1     -12.610  -1.133  -0.785  1.00  0.00           C  
HETATM    5  C5  UNL     1     -11.253  -0.481  -1.171  1.00  0.00           C  
HETATM    6  C6  UNL     1     -11.177  -0.363  -2.637  1.00  0.00           C  
HETATM    7  C7  UNL     1      -9.997   0.229  -3.299  1.00  0.00           C  
HETATM    8  C8  UNL     1      -9.629   1.631  -3.081  1.00  0.00           C  
HETATM    9  C9  UNL     1      -9.223   2.184  -1.808  1.00  0.00           C  
HETATM   10  C10 UNL     1      -7.964   1.782  -1.158  1.00  0.00           C  
HETATM   11  C11 UNL     1      -7.695   0.369  -0.816  1.00  0.00           C  
HETATM   12  C12 UNL     1      -6.430   0.159  -0.017  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.190   0.650  -0.667  1.00  0.00           C  
HETATM   14  O1  UNL     1      -5.218   2.039  -0.889  1.00  0.00           O  
HETATM   15  C14 UNL     1      -3.961   0.328   0.167  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.982   1.056   1.489  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.484   0.953   1.834  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.898   1.106   0.477  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.590   0.443   0.236  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.608  -1.039   0.118  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.900  -1.334   0.142  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.448  -0.069   0.815  1.00  0.00           C  
HETATM   23  C22 UNL     1       2.215  -0.559   2.030  1.00  0.00           C  
HETATM   24  O2  UNL     1       2.608   0.535   2.830  1.00  0.00           O  
HETATM   25  C23 UNL     1       3.445  -1.289   1.537  1.00  0.00           C  
HETATM   26  C24 UNL     1       4.352  -0.392   0.735  1.00  0.00           C  
HETATM   27  C25 UNL     1       5.596  -1.189   0.309  1.00  0.00           C  
HETATM   28  C26 UNL     1       6.530  -0.311  -0.465  1.00  0.00           C  
HETATM   29  C27 UNL     1       7.760  -1.049  -0.870  1.00  0.00           C  
HETATM   30  C28 UNL     1       8.521  -1.594   0.340  1.00  0.00           C  
HETATM   31  C29 UNL     1       8.907  -0.508   1.281  1.00  0.00           C  
HETATM   32  O3  UNL     1       9.592  -1.118   2.357  1.00  0.00           O  
HETATM   33  C30 UNL     1       9.847   0.528   0.735  1.00  0.00           C  
HETATM   34  C31 UNL     1      11.158  -0.105   0.321  1.00  0.00           C  
HETATM   35  C32 UNL     1      12.108   0.944  -0.225  1.00  0.00           C  
HETATM   36  C33 UNL     1      13.389   0.342  -0.605  1.00  0.00           C  
HETATM   37  C34 UNL     1      13.944   0.332  -1.787  1.00  0.00           C  
HETATM   38  C35 UNL     1      15.247  -0.381  -1.763  1.00  0.00           C  
HETATM   39  C36 UNL     1      16.388   0.547  -2.119  1.00  0.00           C  
HETATM   40  O4  UNL     1      15.404  -0.790  -0.422  1.00  0.00           O  
HETATM   41  C37 UNL     1      14.308  -0.376   0.302  1.00  0.00           C  
HETATM   42  O5  UNL     1      14.092  -0.559   1.528  1.00  0.00           O  
HETATM   43  O6  UNL     1       0.348   0.688   1.199  1.00  0.00           O  
HETATM   44  O7  UNL     1      -2.843   0.776  -0.479  1.00  0.00           O  
HETATM   45  H1  UNL     1     -13.367  -1.039   3.166  1.00  0.00           H  
HETATM   46  H2  UNL     1     -12.918   0.694   3.520  1.00  0.00           H  
HETATM   47  H3  UNL     1     -11.651  -0.593   3.314  1.00  0.00           H  
HETATM   48  H4  UNL     1     -13.391   0.722   1.204  1.00  0.00           H  
HETATM   49  H5  UNL     1     -11.594   0.603   1.298  1.00  0.00           H  
HETATM   50  H6  UNL     1     -13.578  -1.756   1.057  1.00  0.00           H  
HETATM   51  H7  UNL     1     -11.746  -1.858   1.025  1.00  0.00           H  
HETATM   52  H8  UNL     1     -12.744  -2.098  -1.273  1.00  0.00           H  
HETATM   53  H9  UNL     1     -13.406  -0.456  -1.173  1.00  0.00           H  
HETATM   54  H10 UNL     1     -11.185   0.446  -0.633  1.00  0.00           H  
HETATM   55  H11 UNL     1     -10.495  -1.256  -0.844  1.00  0.00           H  
HETATM   56  H12 UNL     1     -11.358  -1.423  -3.041  1.00  0.00           H  
HETATM   57  H13 UNL     1     -12.112   0.170  -3.052  1.00  0.00           H  
HETATM   58  H14 UNL     1      -9.138  -0.487  -3.126  1.00  0.00           H  
HETATM   59  H15 UNL     1     -10.207   0.106  -4.449  1.00  0.00           H  
HETATM   60  H16 UNL     1     -10.447   2.320  -3.575  1.00  0.00           H  
HETATM   61  H17 UNL     1      -8.783   1.878  -3.862  1.00  0.00           H  
HETATM   62  H18 UNL     1     -10.025   2.237  -1.015  1.00  0.00           H  
HETATM   63  H19 UNL     1      -9.024   3.343  -2.037  1.00  0.00           H  
HETATM   64  H20 UNL     1      -7.143   2.148  -1.889  1.00  0.00           H  
HETATM   65  H21 UNL     1      -7.823   2.468  -0.257  1.00  0.00           H  
HETATM   66  H22 UNL     1      -8.547  -0.130  -0.301  1.00  0.00           H  
HETATM   67  H23 UNL     1      -7.457  -0.178  -1.795  1.00  0.00           H  
HETATM   68  H24 UNL     1      -6.364  -0.901   0.313  1.00  0.00           H  
HETATM   69  H25 UNL     1      -6.568   0.732   0.950  1.00  0.00           H  
HETATM   70  H26 UNL     1      -5.050   0.158  -1.650  1.00  0.00           H  
HETATM   71  H27 UNL     1      -4.316   2.289  -1.206  1.00  0.00           H  
HETATM   72  H28 UNL     1      -3.938  -0.777   0.356  1.00  0.00           H  
HETATM   73  H29 UNL     1      -4.158   2.134   1.332  1.00  0.00           H  
HETATM   74  H30 UNL     1      -4.624   0.597   2.237  1.00  0.00           H  
HETATM   75  H31 UNL     1      -2.242   0.015   2.355  1.00  0.00           H  
HETATM   76  H32 UNL     1      -2.230   1.821   2.496  1.00  0.00           H  
HETATM   77  H33 UNL     1      -1.709   2.217   0.313  1.00  0.00           H  
HETATM   78  H34 UNL     1      -0.194   0.834  -0.740  1.00  0.00           H  
HETATM   79  H35 UNL     1      -1.054  -1.574   0.963  1.00  0.00           H  
HETATM   80  H36 UNL     1      -1.039  -1.343  -0.860  1.00  0.00           H  
HETATM   81  H37 UNL     1       1.217  -1.391  -0.903  1.00  0.00           H  
HETATM   82  H38 UNL     1       1.103  -2.234   0.744  1.00  0.00           H  
HETATM   83  H39 UNL     1       2.040   0.556   0.142  1.00  0.00           H  
HETATM   84  H40 UNL     1       1.581  -1.219   2.612  1.00  0.00           H  
HETATM   85  H41 UNL     1       3.046   0.100   3.628  1.00  0.00           H  
HETATM   86  H42 UNL     1       3.102  -2.122   0.890  1.00  0.00           H  
HETATM   87  H43 UNL     1       4.035  -1.747   2.361  1.00  0.00           H  
HETATM   88  H44 UNL     1       4.730   0.454   1.346  1.00  0.00           H  
HETATM   89  H45 UNL     1       3.925  -0.011  -0.196  1.00  0.00           H  
HETATM   90  H46 UNL     1       5.305  -2.043  -0.332  1.00  0.00           H  
HETATM   91  H47 UNL     1       6.056  -1.603   1.223  1.00  0.00           H  
HETATM   92  H48 UNL     1       6.751   0.585   0.172  1.00  0.00           H  
HETATM   93  H49 UNL     1       6.063   0.104  -1.386  1.00  0.00           H  
HETATM   94  H50 UNL     1       8.413  -0.477  -1.536  1.00  0.00           H  
HETATM   95  H51 UNL     1       7.437  -1.948  -1.454  1.00  0.00           H  
HETATM   96  H52 UNL     1       9.443  -2.051  -0.082  1.00  0.00           H  
HETATM   97  H53 UNL     1       7.877  -2.314   0.842  1.00  0.00           H  
HETATM   98  H54 UNL     1       8.019  -0.032   1.750  1.00  0.00           H  
HETATM   99  H55 UNL     1       9.242  -2.026   2.522  1.00  0.00           H  
HETATM  100  H56 UNL     1      10.039   1.255   1.565  1.00  0.00           H  
HETATM  101  H57 UNL     1       9.402   1.126  -0.087  1.00  0.00           H  
HETATM  102  H58 UNL     1      11.630  -0.632   1.172  1.00  0.00           H  
HETATM  103  H59 UNL     1      11.004  -0.843  -0.490  1.00  0.00           H  
HETATM  104  H60 UNL     1      12.212   1.737   0.555  1.00  0.00           H  
HETATM  105  H61 UNL     1      11.648   1.400  -1.114  1.00  0.00           H  
HETATM  106  H62 UNL     1      13.543   0.772  -2.691  1.00  0.00           H  
HETATM  107  H63 UNL     1      15.246  -1.282  -2.408  1.00  0.00           H  
HETATM  108  H64 UNL     1      16.552   0.483  -3.218  1.00  0.00           H  
HETATM  109  H65 UNL     1      16.108   1.576  -1.843  1.00  0.00           H  
HETATM  110  H66 UNL     1      17.342   0.225  -1.648  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3   48   49
CONECT    3    4   50   51
CONECT    4    5   52   53
CONECT    5    6   54   55
CONECT    6    7   56   57
CONECT    7    8   58   59
CONECT    8    9   60   61
CONECT    9   10   62   63
CONECT   10   11   64   65
CONECT   11   12   66   67
CONECT   12   13   68   69
CONECT   13   14   15   70
CONECT   14   71
CONECT   15   16   44   72
CONECT   16   17   73   74
CONECT   17   18   75   76
CONECT   18   19   44   77
CONECT   19   20   43   78
CONECT   20   21   79   80
CONECT   21   22   81   82
CONECT   22   23   43   83
CONECT   23   24   25   84
CONECT   24   85
CONECT   25   26   86   87
CONECT   26   27   88   89
CONECT   27   28   90   91
CONECT   28   29   92   93
CONECT   29   30   94   95
CONECT   30   31   96   97
CONECT   31   32   33   98
CONECT   32   99
CONECT   33   34  100  101
CONECT   34   35  102  103
CONECT   35   36  104  105
CONECT   36   37   37   41
CONECT   37   38  106
CONECT   38   39   40  107
CONECT   39  108  109  110
CONECT   40   41
CONECT   41   42   42
END

HMDB0036363
     RDKit          3D
4-Deoxy-6-hydroxysquamotacin
110112  0  0  0  0  0  0  0  0999 V2000
  -12.6378   -0.2404    2.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5558    0.0442    1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6461   -1.2441    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6102   -1.1333   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2534   -0.4813   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1766   -0.3632   -2.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9969    0.2287   -3.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6289    1.6306   -3.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2226    2.1837   -1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9644    1.7819   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6951    0.3693   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    0.1595   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    0.6499   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    2.0389   -0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9610    0.3279    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823    1.0561    1.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    0.9529    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983    1.1064    0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900    0.4430    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -1.0389    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995   -1.3340    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -0.0686    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147   -0.5588    2.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078    0.5350    2.8299 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447   -1.2892    1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -0.3916    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -1.1886    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5302   -0.3106   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7596   -1.0493   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5206   -1.5935    0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9065   -0.5076    1.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5920   -1.1181    2.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8472    0.5276    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1583   -0.1050    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1084    0.9444   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3894    0.3422   -0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9440    0.3316   -1.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2468   -0.3812   -1.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3878    0.5471   -2.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4040   -0.7900   -0.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3084   -0.3757    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0917   -0.5585    1.5277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3484    0.6881    1.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    0.7765   -0.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3671   -1.0395    3.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9183    0.6939    3.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6506   -0.5933    3.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3913    0.7222    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5944    0.6026    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5782   -1.7564    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7459   -1.8575    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7439   -2.0982   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4062   -0.4556   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1850    0.4459   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4954   -1.2561   -0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3577   -1.4233   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1118    0.1703   -3.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1383   -0.4870   -3.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2068    0.1064   -4.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4472    2.3200   -3.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7831    1.8776   -3.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0248    2.2373   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0237    3.3428   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1429    2.1482   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8231    2.4679   -0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5475   -0.1304   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4570   -0.1783   -1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3638   -0.9014    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5676    0.7316    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503    0.1577   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159    2.2886   -1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -0.7767    0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    2.1340    1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6240    0.5969    2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    0.0154    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297    1.8206    2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    2.2173    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.8339   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538   -1.5738    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.3432   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172   -1.3912   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034   -2.2343    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    0.5557    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810   -1.2195    2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456    0.1003    3.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.1221    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -1.7469    2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    0.4541    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252   -0.0106   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3050   -2.0434   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0565   -1.6027    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7510    0.5846    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0633    0.1036   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4126   -0.4774   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368   -1.9483   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4429   -2.0511   -0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8772   -2.3142    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0192   -0.0325    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -2.0261    2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0391    1.2545    1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4015    1.1261   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6300   -0.6323    1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0039   -0.8427   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2121    1.7372    0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6481    1.4002   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5432    0.7725   -2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2465   -1.2823   -2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5519    0.4832   -3.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1076    1.5760   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3417    0.2250   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
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 34 35  1  0
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 22 43  1  0
 18 44  1  0
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  1 45  1  0
  1 46  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₇H₆₆O₇

Average Molecular Weight

622.9157

Monoisotopic Molecular Weight

622.480854466

IUPAC Name

3-(4,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(4,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCC(O)CCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-16-13-12-14-19-30(38)20-17-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3

InChI Key

WWLPFTIHLMRECR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0036363)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036363)

Source

Endogenous

Endogenous (HMDB: HMDB0036363)

Plant

Plant (HMDB: HMDB0036363)

Animal

Animal (HMDB: HMDB0036363)

Exogenous

Food

Food (HMDB: HMDB0036363)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0036363)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036363)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036363)

Lipid metabolism pathway (HMDB: HMDB0036363)

Cellular process

Cell signaling (HMDB: HMDB0036363)

Biochemical process

Lipid transport (HMDB: HMDB0036363)

Role

Biological role

Energy source (HMDB: HMDB0036363)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036363)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00057 g/L	ALOGPS
logP	6.9	ALOGPS
logP	8.68	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	176.4 m³·mol⁻¹	ChemAxon
Polarizability	78.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	253.242	31661259
DarkChem	[M-H]-	246.676	31661259
DeepCCS	[M+H]+	258.353	30932474
DeepCCS	[M-H]-	255.995	30932474
DeepCCS	[M-2H]-	288.879	30932474
DeepCCS	[M+Na]+	264.446	30932474
AllCCS	[M+H]+	274.7	32859911
AllCCS	[M+H-H2O]+	273.7	32859911
AllCCS	[M+NH4]+	275.6	32859911
AllCCS	[M+Na]+	275.9	32859911
AllCCS	[M-H]-	241.6	32859911
AllCCS	[M+Na-2H]-	246.3	32859911
AllCCS	[M+HCOO]-	251.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Deoxy-6-hydroxysquamotacin	CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCC(O)CCCC1=CC(C)OC1=O	4771.5	Standard polar	33892256
4-Deoxy-6-hydroxysquamotacin	CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCC(O)CCCC1=CC(C)OC1=O	4383.2	Standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin	CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCC(O)CCCC1=CC(C)OC1=O	4658.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Deoxy-6-hydroxysquamotacin,1TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCCCC(O)CCCC3=CC(C)OC3=O)O2)O1	4787.6	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,1TMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCC(O)CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1	4788.0	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,1TMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1	4810.4	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCCCC(O)CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1	4728.8	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TMS,isomer #2	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1	4746.2	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O1	4746.7	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,3TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O1	4688.0	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,1TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCCCC(O)CCCC3=CC(C)OC3=O)O2)O1	5001.2	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,1TBDMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCC(O)CCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1	5001.5	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,1TBDMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1	5027.0	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(CCCCCCC(O)CCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1	5166.5	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TBDMS,isomer #2	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1	5180.2	Semi standard non polar	33892256
4-Deoxy-6-hydroxysquamotacin,2TBDMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCC(CCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)O1	5180.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h90-0649722000-603c86f95975f16ac35b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (1 TMS) - 70eV, Positive	splash10-024i-4136934000-94c40d0b8472d5b97909	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxy-6-hydroxysquamotacin GC-MS ("4-Deoxy-6-hydroxysquamotacin,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 10V, Positive-QTOF	splash10-0ab9-0112039000-8a8dbc9735475ca27dd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 20V, Positive-QTOF	splash10-05n0-2932142000-1e3de7b3fffc9724eae6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 40V, Positive-QTOF	splash10-014i-9824220000-070ac191b07be2561e94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 10V, Negative-QTOF	splash10-00di-0000039000-bb3b9e02e5afdb4df063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 20V, Negative-QTOF	splash10-0uk9-1353339000-d96b4a79690f3b24395d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 40V, Negative-QTOF	splash10-0iru-2379130000-2a4c278c1a2c32f1d27d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 10V, Negative-QTOF	splash10-00di-0000109000-381f3adfad349f88edfb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 20V, Negative-QTOF	splash10-00di-2122639000-9724074d8d6a7ae06c45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 40V, Negative-QTOF	splash10-0609-8835902000-57d24cfc9832d23a41e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 10V, Positive-QTOF	splash10-052r-2210296000-163e481a6967ddbbb0f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 20V, Positive-QTOF	splash10-0adr-1000195000-ecc8b616fb0c72479811	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-6-hydroxysquamotacin 40V, Positive-QTOF	splash10-0006-9000100000-bdf047f4a6631552d8d7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015238

KNApSAcK ID

C00054533

Chemspider ID

35014125

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751973

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-Deoxy-6-hydroxysquamotacin (HMDB0036363)

MOL for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

3D MOL for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

3D SDF for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

3D-SDF for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

PDB for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

3D PDB for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

SMILES for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

INCHI for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

Structure for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

3D Structure for HMDB0036363 (4-Deoxy-6-hydroxysquamotacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra