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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:52 UTC

Update Date

2022-03-07 02:52:22 UTC

HMDB ID

HMDB0029969

Secondary Accession Numbers

HMDB29969

Metabolite Identification

Common Name

Squamostanal A

Description

Squamostanal A 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 Squamostanal A.

Structure

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

HMDB0029969
     RDKit          3D
Squamostanal A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -7.6561    0.3218   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4062   -0.5225   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7708   -0.0752    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    0.4800    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    1.0559    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3721    0.2643    1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    0.7446    2.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    0.0867    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    0.1030    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.4414   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.4140   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -1.1920   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763   -1.1638   -1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.2307   -2.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749    0.8434   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1156    0.0791   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531    0.7708    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056    1.7756    1.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313    0.4329   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    0.8963   -1.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.1792   -1.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3166   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2967   -0.1387   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1458    0.4595    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6595   -1.6092   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1674   -0.1724    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    2.1046    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    0.9878    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.7788    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.2464    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5692    3.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.8802    2.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -1.0185    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    0.4166    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896   -0.5346    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    1.1574    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    0.3105   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.3993   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    0.6311   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -0.8646   -2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734   -0.8235    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -2.2695   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -1.6683   -2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.7742   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246    0.8363   -2.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2724    0.2022   -2.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    1.9046   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828    0.9513   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054   -0.9410    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9977    0.0187   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3638    0.3731    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
M  END

  Mrv0541 02241210462D          

 21 21  0  0  0  0            999 V2000
   -4.9107    0.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1657   -0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5000   -0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2240    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5085    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0688    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7843    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996    0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0427   -0.6079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9541   -0.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9541    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 19  2  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029969

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-16-15-17(18(20)21-16)13-11-9-7-5-3-2-4-6-8-10-12-14-19/h14-16H,2-13H2,1H3

> <INCHI_KEY>
CWCAGZXBGYHWNE-UHFFFAOYSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.56554618503864

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecanal

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
5.2047070653333325

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.68998366856935

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.98085258404318

> <JCHEM_PKA_STRONGEST_BASIC>
-6.60987358903905

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
85.97529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(5-methyl-2-oxo-5H-furan-3-yl)tridecanal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029969
     RDKit          3D
Squamostanal A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -7.6561    0.3218   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4062   -0.5225   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7708   -0.0752    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    0.4800    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    1.0559    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3721    0.2643    1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    0.7446    2.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    0.0867    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    0.1030    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.4414   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.4140   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -1.1920   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763   -1.1638   -1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.2307   -2.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749    0.8434   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1156    0.0791   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531    0.7708    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056    1.7756    1.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313    0.4329   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    0.8963   -1.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.1792   -1.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3166   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2967   -0.1387   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1458    0.4595    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6595   -1.6092   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1674   -0.1724    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    2.1046    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    0.9878    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.7788    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.2464    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5692    3.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.8802    2.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -1.0185    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    0.4166    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896   -0.5346    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    1.1574    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    0.3105   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.3993   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    0.6311   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -0.8646   -2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734   -0.8235    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -2.2695   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -1.6683   -2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.7742   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246    0.8363   -2.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2724    0.2022   -2.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    1.9046   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828    0.9513   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054   -0.9410    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9977    0.0187   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3638    0.3731    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  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      -9.167   0.813   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.643  -0.658   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.400  -1.567   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.151  -0.658   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.627   0.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.292   1.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.956   0.801   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.621   1.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.285   0.801   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.949   1.567   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.386   0.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.721   1.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.057   0.801   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.393   1.567   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.728   0.801   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.064   1.567   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.399   0.801   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.735   1.567   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.680  -1.135   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -11.114  -1.135   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.114   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   21                                                       
CONECT   19    4                                                            
CONECT   20    2                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0029969
HETATM    1  C1  UNL     1      -7.656   0.322  -0.847  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.406  -0.522  -0.655  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.771  -0.075   0.585  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.621   0.480   0.325  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.686   1.056   1.343  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.372   0.264   1.214  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.360   0.745   2.177  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.057   0.087   2.206  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.901   0.103   1.110  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.533  -0.441  -0.206  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.681  -0.414  -1.210  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.874  -1.192  -0.812  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.976  -1.164  -1.840  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.461   0.231  -2.108  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.975   0.843  -0.839  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.116   0.079  -0.225  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.553   0.771   1.019  1.00  0.00           C  
HETATM   18  O1  UNL     1       6.006   1.776   1.377  1.00  0.00           O  
HETATM   19  C18 UNL     1      -4.431   0.433  -1.112  1.00  0.00           C  
HETATM   20  O2  UNL     1      -3.399   0.896  -1.698  1.00  0.00           O  
HETATM   21  O3  UNL     1      -5.531  -0.179  -1.682  1.00  0.00           O  
HETATM   22  H1  UNL     1      -7.325   1.317  -1.205  1.00  0.00           H  
HETATM   23  H2  UNL     1      -8.297  -0.139  -1.612  1.00  0.00           H  
HETATM   24  H3  UNL     1      -8.146   0.459   0.127  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.660  -1.609  -0.646  1.00  0.00           H  
HETATM   26  H5  UNL     1      -6.167  -0.172   1.604  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.490   2.105   1.070  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.107   0.988   2.345  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.681  -0.779   1.545  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.163   0.246   0.164  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.822   0.569   3.213  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.286   1.880   2.180  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.243  -1.018   2.506  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.533   0.417   3.147  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.790  -0.535   1.464  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.282   1.157   0.970  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.182   0.311  -0.680  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.006  -1.399  -0.167  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.943   0.631  -1.470  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.261  -0.865  -2.151  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.273  -0.824   0.173  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.664  -2.270  -0.623  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.644  -1.668  -2.792  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.854  -1.774  -1.516  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.625   0.836  -2.501  1.00  0.00           H  
HETATM   46  H25 UNL     1       5.272   0.202  -2.883  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.289   1.905  -1.074  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.183   0.951  -0.076  1.00  0.00           H  
HETATM   49  H28 UNL     1       5.805  -0.941   0.055  1.00  0.00           H  
HETATM   50  H29 UNL     1       6.998   0.019  -0.891  1.00  0.00           H  
HETATM   51  H30 UNL     1       7.364   0.373   1.604  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21   25
CONECT    3    4    4   26
CONECT    4    5   19
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   18   51
CONECT   19   20   20   21
END

HMDB0029969
     RDKit          3D
Squamostanal A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -7.6561    0.3218   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4062   -0.5225   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7708   -0.0752    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6206    0.4800    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    1.0559    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3721    0.2643    1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    0.7446    2.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    0.0867    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008    0.1030    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.4414   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.4140   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -1.1920   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763   -1.1638   -1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.2307   -2.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9749    0.8434   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1156    0.0791   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531    0.7708    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056    1.7756    1.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313    0.4329   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    0.8963   -1.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306   -0.1792   -1.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3166   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2967   -0.1387   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1458    0.4595    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6595   -1.6092   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1674   -0.1724    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    2.1046    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    0.9878    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.7788    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    0.2464    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224    0.5692    3.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.8802    2.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -1.0185    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    0.4166    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896   -0.5346    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    1.1574    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    0.3105   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.3993   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    0.6311   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -0.8646   -2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734   -0.8235    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -2.2695   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -1.6683   -2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.7742   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246    0.8363   -2.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2724    0.2022   -2.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    1.9046   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828    0.9513   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054   -0.9410    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9977    0.0187   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3638    0.3731    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecanal

Traditional Name

13-(5-methyl-2-oxo-5H-furan-3-yl)tridecanal

CAS Registry Number

156764-90-8

SMILES

CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1

InChI Identifier

InChI=1S/C18H30O3/c1-16-15-17(18(20)21-16)13-11-9-7-5-3-2-4-6-8-10-12-14-19/h14-16H,2-13H2,1H3

InChI Key

CWCAGZXBGYHWNE-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
2-furanone
Alpha-hydrogen aldehyde
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Aldehyde
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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: HMDB0029969)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029969)

Source

Endogenous

Endogenous (HMDB: HMDB0029969)

Plant

Plant (HMDB: HMDB0029969)

Animal

Animal (HMDB: HMDB0029969)

Exogenous

Food

Food (HMDB: HMDB0029969)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029969)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0029969)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0029969)

Lipid metabolism pathway (HMDB: HMDB0029969)

Biochemical process

Lipid transport (HMDB: HMDB0029969)

Role

Biological role

Energy source (HMDB: HMDB0029969)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	66 - 68 °C	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	0.0012 g/L	ALOGPS
logP	5.24	ALOGPS
logP	5.2	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	85.98 m³·mol⁻¹	ChemAxon
Polarizability	36.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.56	31661259
DarkChem	[M-H]-	174.792	31661259
DeepCCS	[M+H]+	175.281	30932474
DeepCCS	[M-H]-	172.923	30932474
DeepCCS	[M-2H]-	205.879	30932474
DeepCCS	[M+Na]+	181.375	30932474
AllCCS	[M+H]+	179.4	32859911
AllCCS	[M+H-H2O]+	176.4	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	180.7	32859911
AllCCS	[M+Na-2H]-	181.7	32859911
AllCCS	[M+HCOO]-	183.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Squamostanal A	CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1	3158.4	Standard polar	33892256
Squamostanal A	CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1	2319.1	Standard non polar	33892256
Squamostanal A	CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1	2427.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Squamostanal A,1TMS,isomer #1	CC1C=C(CCCCCCCCCCCC=CO[Si](C)(C)C)C(=O)O1	2529.3	Semi standard non polar	33892256
Squamostanal A,1TMS,isomer #1	CC1C=C(CCCCCCCCCCCC=CO[Si](C)(C)C)C(=O)O1	2504.5	Standard non polar	33892256
Squamostanal A,1TBDMS,isomer #1	CC1C=C(CCCCCCCCCCCC=CO[Si](C)(C)C(C)(C)C)C(=O)O1	2769.3	Semi standard non polar	33892256
Squamostanal A,1TBDMS,isomer #1	CC1C=C(CCCCCCCCCCCC=CO[Si](C)(C)C(C)(C)C)C(=O)O1	2720.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Squamostanal A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ukc-3490000000-7b1ff54f858aadbde4b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Squamostanal A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Squamostanal A 10V, Positive-QTOF	splash10-0002-0090000000-d4ba155bce276c94202a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Positive-QTOF	splash10-0006-9570000000-c2d943e2d84d0422cb59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Positive-QTOF	splash10-0fr6-7930000000-00efa5845f6074e39d76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Negative-QTOF	splash10-0006-0090000000-728d4f1b4fb067f52fb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Negative-QTOF	splash10-0007-2090000000-74b8c5488052f72e63fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Negative-QTOF	splash10-0006-9030000000-c937dc895cdf6ba2d727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Positive-QTOF	splash10-0002-1390000000-1fae30d70610a199c197	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Positive-QTOF	splash10-0002-6590000000-ac52a0b936f35402e4e5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Positive-QTOF	splash10-0537-9300000000-b93947502ce8ca261758	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Negative-QTOF	splash10-0006-0090000000-55e62f9f2f7dcc1fe39a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Negative-QTOF	splash10-0005-0090000000-69fb163913a9f7be08af	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Negative-QTOF	splash10-05tb-3390000000-d020349e68b4ea57ec08	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB001256

KNApSAcK ID

C00057939

Chemspider ID

35013109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85308895

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 Squamostanal A (HMDB0029969)

MOL for HMDB0029969 (Squamostanal A)

3D MOL for HMDB0029969 (Squamostanal A)

3D SDF for HMDB0029969 (Squamostanal A)

3D-SDF for HMDB0029969 (Squamostanal A)

PDB for HMDB0029969 (Squamostanal A)

3D PDB for HMDB0029969 (Squamostanal A)

SMILES for HMDB0029969 (Squamostanal A)

INCHI for HMDB0029969 (Squamostanal A)

Structure for HMDB0029969 (Squamostanal A)

3D Structure for HMDB0029969 (Squamostanal A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra