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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:16:50 UTC

Update Date

2022-03-07 02:57:05 UTC

HMDB ID

HMDB0041587

Secondary Accession Numbers

HMDB41587

Metabolite Identification

Common Name

Macrocarpal I

Description

Macrocarpal I belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on Macrocarpal I.

Structure

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


  Mrv0541 02241218542D          

 35 37  0  0  0  0            999 V2000
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 32 33  1  0  0  0  0
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 32 35  1  0  0  0  0
M  END

HMDB0041587
     RDKit          3D
Macrocarpal I
 77 79  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02241218542D          

 35 37  0  0  0  0            999 V2000
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 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 29  1  0  0  0  0
 22 30  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 28  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041587

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(C1CCC(C)(O)C2CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O7/c1-15(2)11-17(22-24(32)18(13-29)23(31)19(14-30)25(22)33)20-8-10-28(6,35)21-12-16(26(3,4)34)7-9-27(20,21)5/h13-17,20-21,31-35H,7-12H2,1-6H3

> <INCHI_KEY>
PXQFFMATXFLUPK-UHFFFAOYSA-N

> <FORMULA>
C28H42O7

> <MOLECULAR_WEIGHT>
490.6289

> <EXACT_MASS>
490.293053698

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
53.94171810771151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,6-trihydroxy-5-{1-[4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
7.0070424849999995

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.76755206619906

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.688077014154504

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3574850426025956

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
136.9206

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,6-trihydroxy-5-{1-[4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041587
     RDKit          3D
Macrocarpal I
 77 79  0  0  0  0  0  0  0  0999 V2000
   -4.3407   -0.3288   -1.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2854   -1.3142   -2.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -2.4915   -2.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3877   -1.8438   -1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.9405   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836   -0.0449    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608    1.2951    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9739    1.8832   -0.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955    2.0881    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3988    3.5048    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    4.2524    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087    1.5108    2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6552    2.2130    3.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606    0.1201    2.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4406   -0.4393    3.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295   -1.6367    3.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -0.6072    1.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -1.9643    1.6028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -0.3923   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -1.6294   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182   -2.6364   -0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584   -2.0537   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -2.6260    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -2.4144   -1.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.5499   -0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    0.0469    0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    1.4668   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882    2.1429    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    1.3681   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231    2.2519    1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941    3.4186   -0.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872    2.1687    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    1.5204   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333    0.0311   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -0.2946    1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    0.7207   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2991   -0.4976   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6348   -0.4548   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -0.8909   -3.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -2.8892   -3.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -3.3152   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -2.1422   -3.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -2.7867   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862   -2.3126   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.6355    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110    2.8314   -1.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    4.0049   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8920    3.1248    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0098    0.2375    4.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -2.5391    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3779    0.2970   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094   -1.2766   -2.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274   -2.0416   -2.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -3.5495   -1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -3.0125   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695   -3.6326    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858   -2.0380    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -2.8838    0.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811   -3.2046   -1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138   -0.1840   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -0.1278    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2317   -0.4735   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    1.4356   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    0.9874   -1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767    0.5311    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6802    2.0761   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    3.1266    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9232    2.3396    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843    1.3159    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306    3.2855   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    2.4032    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    3.1989   -0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525    1.8707   -1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507    1.9056    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.3584    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518    0.0995    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -1.3372    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 14 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 27 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 17  6  1  0
 34 19  1  0
 34 25  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  8 46  1  0
 10 47  1  0
 13 48  1  0
 15 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 31 70  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  0
 33 74  1  0
 35 75  1  0
 35 76  1  0
 35 77  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      -3.997   2.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.997   1.159   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.665   0.389   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.336   1.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.336   2.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.665   3.466   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.001   0.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.333   1.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.333   2.699   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.668   3.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.001   3.469   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.336   4.239   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.665   5.006   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.000   5.776   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.330   3.469   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.332   0.389   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.666   1.159   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.665  -1.151   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.001  -1.151   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.336  -1.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.336  -3.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.001  -4.236   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.330  -3.466   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.330  -1.924   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.665  -4.236   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.997  -3.466   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.997  -1.924   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.665  -1.156   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.771  -5.571   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.769  -5.571   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.330  -0.384   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.332  -4.236   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.666  -3.466   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.332  -5.776   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.666  -5.006   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   12                                                  
CONECT    6    1    5   13                                                  
CONECT    7    4    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5                                                            
CONECT   13    6   14                                                       
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16    2   17                                                       
CONECT   17   16                                                            
CONECT   18    3                                                            
CONECT   19    7   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29   30                                             
CONECT   23   22   24   25                                                  
CONECT   24   19   23   28   31                                             
CONECT   25   23   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   24   27                                                       
CONECT   29   22                                                            
CONECT   30   22                                                            
CONECT   31   24                                                            
CONECT   32   26   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0041587
HETATM    1  C1  UNL     1      -4.341  -0.329  -1.882  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.285  -1.314  -2.269  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.083  -2.491  -2.893  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.388  -1.844  -1.240  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.483  -0.940  -0.449  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.384  -0.045   0.295  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.561   1.295   0.173  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.974   1.883  -0.909  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.296   2.088   1.049  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.399   3.505   0.795  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.050   4.252   1.558  1.00  0.00           O  
HETATM   12  C10 UNL     1      -3.909   1.511   2.133  1.00  0.00           C  
HETATM   13  O3  UNL     1      -4.655   2.213   3.053  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.761   0.120   2.308  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.441  -0.439   3.473  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.430  -1.637   3.798  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.031  -0.607   1.425  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.881  -1.964   1.603  1.00  0.00           O  
HETATM   19  C14 UNL     1      -0.282  -0.392  -1.124  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.389  -1.629  -1.798  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.918  -2.636  -0.867  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.258  -2.054  -0.398  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.764  -2.626   0.859  1.00  0.00           C  
HETATM   24  O6  UNL     1       3.175  -2.414  -1.421  1.00  0.00           O  
HETATM   25  C19 UNL     1       2.177  -0.550  -0.481  1.00  0.00           C  
HETATM   26  C20 UNL     1       3.295   0.047   0.344  1.00  0.00           C  
HETATM   27  C21 UNL     1       3.423   1.467  -0.112  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.688   2.143   0.286  1.00  0.00           C  
HETATM   29  C23 UNL     1       5.844   1.368  -0.318  1.00  0.00           C  
HETATM   30  C24 UNL     1       4.823   2.252   1.791  1.00  0.00           C  
HETATM   31  O7  UNL     1       4.694   3.419  -0.276  1.00  0.00           O  
HETATM   32  C25 UNL     1       2.187   2.169   0.308  1.00  0.00           C  
HETATM   33  C26 UNL     1       0.950   1.520  -0.192  1.00  0.00           C  
HETATM   34  C27 UNL     1       0.833   0.031  -0.116  1.00  0.00           C  
HETATM   35  C28 UNL     1       0.461  -0.295   1.311  1.00  0.00           C  
HETATM   36  H1  UNL     1      -4.090   0.721  -2.136  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.299  -0.498  -2.466  1.00  0.00           H  
HETATM   38  H3  UNL     1      -4.635  -0.455  -0.832  1.00  0.00           H  
HETATM   39  H4  UNL     1      -2.762  -0.891  -3.163  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.520  -2.889  -3.763  1.00  0.00           H  
HETATM   41  H6  UNL     1      -4.158  -3.315  -2.155  1.00  0.00           H  
HETATM   42  H7  UNL     1      -5.059  -2.142  -3.269  1.00  0.00           H  
HETATM   43  H8  UNL     1      -1.839  -2.787  -1.568  1.00  0.00           H  
HETATM   44  H9  UNL     1      -3.086  -2.313  -0.471  1.00  0.00           H  
HETATM   45  H10 UNL     1      -1.060  -1.636   0.311  1.00  0.00           H  
HETATM   46  H11 UNL     1      -2.011   2.831  -1.128  1.00  0.00           H  
HETATM   47  H12 UNL     1      -2.940   4.005  -0.039  1.00  0.00           H  
HETATM   48  H13 UNL     1      -4.892   3.125   3.153  1.00  0.00           H  
HETATM   49  H14 UNL     1      -5.010   0.237   4.119  1.00  0.00           H  
HETATM   50  H15 UNL     1      -3.229  -2.539   2.294  1.00  0.00           H  
HETATM   51  H16 UNL     1      -0.378   0.297  -1.939  1.00  0.00           H  
HETATM   52  H17 UNL     1       1.209  -1.277  -2.455  1.00  0.00           H  
HETATM   53  H18 UNL     1      -0.327  -2.042  -2.559  1.00  0.00           H  
HETATM   54  H19 UNL     1       1.158  -3.550  -1.497  1.00  0.00           H  
HETATM   55  H20 UNL     1       0.293  -3.013  -0.071  1.00  0.00           H  
HETATM   56  H21 UNL     1       2.269  -3.633   1.006  1.00  0.00           H  
HETATM   57  H22 UNL     1       2.686  -2.038   1.772  1.00  0.00           H  
HETATM   58  H23 UNL     1       3.865  -2.884   0.780  1.00  0.00           H  
HETATM   59  H24 UNL     1       2.881  -3.205  -1.918  1.00  0.00           H  
HETATM   60  H25 UNL     1       2.414  -0.184  -1.506  1.00  0.00           H  
HETATM   61  H26 UNL     1       3.261  -0.128   1.405  1.00  0.00           H  
HETATM   62  H27 UNL     1       4.232  -0.474  -0.019  1.00  0.00           H  
HETATM   63  H28 UNL     1       3.416   1.436  -1.238  1.00  0.00           H  
HETATM   64  H29 UNL     1       5.479   0.987  -1.292  1.00  0.00           H  
HETATM   65  H30 UNL     1       6.077   0.531   0.366  1.00  0.00           H  
HETATM   66  H31 UNL     1       6.680   2.076  -0.427  1.00  0.00           H  
HETATM   67  H32 UNL     1       4.285   3.127   2.193  1.00  0.00           H  
HETATM   68  H33 UNL     1       5.923   2.340   2.030  1.00  0.00           H  
HETATM   69  H34 UNL     1       4.484   1.316   2.268  1.00  0.00           H  
HETATM   70  H35 UNL     1       4.731   3.286  -1.267  1.00  0.00           H  
HETATM   71  H36 UNL     1       2.160   2.403   1.399  1.00  0.00           H  
HETATM   72  H37 UNL     1       2.219   3.199  -0.164  1.00  0.00           H  
HETATM   73  H38 UNL     1       0.753   1.871  -1.225  1.00  0.00           H  
HETATM   74  H39 UNL     1       0.151   1.906   0.537  1.00  0.00           H  
HETATM   75  H40 UNL     1      -0.346   0.358   1.623  1.00  0.00           H  
HETATM   76  H41 UNL     1       1.352   0.100   1.909  1.00  0.00           H  
HETATM   77  H42 UNL     1       0.415  -1.337   1.582  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    4   39
CONECT    3   40   41   42
CONECT    4    5   43   44
CONECT    5    6   19   45
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   46
CONECT    9   10   12   12
CONECT   10   11   11   47
CONECT   12   13   14
CONECT   13   48
CONECT   14   15   17   17
CONECT   15   16   16   49
CONECT   17   18
CONECT   18   50
CONECT   19   20   34   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   24   25
CONECT   23   56   57   58
CONECT   24   59
CONECT   25   26   34   60
CONECT   26   27   61   62
CONECT   27   28   32   63
CONECT   28   29   30   31
CONECT   29   64   65   66
CONECT   30   67   68   69
CONECT   31   70
CONECT   32   33   71   72
CONECT   33   34   73   74
CONECT   34   35
CONECT   35   75   76   77
END

HMDB0041587
     RDKit          3D
Macrocarpal I
 77 79  0  0  0  0  0  0  0  0999 V2000
   -4.3407   -0.3288   -1.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2854   -1.3142   -2.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -2.4915   -2.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3877   -1.8438   -1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.9405   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836   -0.0449    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608    1.2951    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9739    1.8832   -0.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955    2.0881    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3988    3.5048    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    4.2524    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087    1.5108    2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6552    2.2130    3.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606    0.1201    2.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4406   -0.4393    3.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295   -1.6367    3.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -0.6072    1.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -1.9643    1.6028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -0.3923   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -1.6294   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182   -2.6364   -0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584   -2.0537   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -2.6260    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -2.4144   -1.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.5499   -0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    0.0469    0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    1.4668   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882    2.1429    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    1.3681   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231    2.2519    1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941    3.4186   -0.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872    2.1687    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    1.5204   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333    0.0311   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -0.2946    1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    0.7207   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2991   -0.4976   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6348   -0.4548   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -0.8909   -3.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -2.8892   -3.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -3.3152   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -2.1422   -3.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -2.7867   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862   -2.3126   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.6355    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110    2.8314   -1.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    4.0049   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8920    3.1248    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0098    0.2375    4.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2292   -2.5391    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3779    0.2970   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094   -1.2766   -2.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274   -2.0416   -2.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -3.5495   -1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -3.0125   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695   -3.6326    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858   -2.0380    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -2.8838    0.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811   -3.2046   -1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138   -0.1840   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -0.1278    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2317   -0.4735   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    1.4356   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    0.9874   -1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767    0.5311    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6802    2.0761   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    3.1266    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9232    2.3396    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4843    1.3159    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306    3.2855   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    2.4032    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    3.1989   -0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525    1.8707   -1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507    1.9056    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.3584    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518    0.0995    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -1.3372    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 14 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 27 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 17  6  1  0
 34 19  1  0
 34 25  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  8 46  1  0
 10 47  1  0
 13 48  1  0
 15 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 31 70  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  0
 33 74  1  0
 35 75  1  0
 35 76  1  0
 35 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Macrocarpal I	MeSH

Chemical Formula

C₂₈H₄₂O₇

Average Molecular Weight

490.6289

Monoisotopic Molecular Weight

490.293053698

IUPAC Name

2,4,6-trihydroxy-5-{1-[4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde

Traditional Name

2,4,6-trihydroxy-5-{1-[4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde

CAS Registry Number

179388-54-6

SMILES

CC(C)CC(C1CCC(C)(O)C2CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

InChI Identifier

InChI=1S/C28H42O7/c1-15(2)11-17(22-24(32)18(13-29)23(31)19(14-30)25(22)33)20-8-10-28(6,35)21-12-16(26(3,4)34)7-9-27(20,21)5/h13-17,20-21,31-35H,7-12H2,1-6H3

InChI Key

PXQFFMATXFLUPK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Acylphloroglucinol derivative
Benzenetriol
Hydroxybenzaldehyde
Phloroglucinol derivative
Benzaldehyde
Benzoyl
Aryl-aldehyde
Phenol
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041587)
Membrane (HMDB: HMDB0041587)

Source

Endogenous

Endogenous (HMDB: HMDB0041587)

Exogenous

Exogenous (HMDB: HMDB0041587)

Process

Not Available

Role

Not Available

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	8.8e-05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.27	ALOGPS
logP	7.01	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.69	ChemAxon
pKa (Strongest Basic)	-0.36	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.92 m³·mol⁻¹	ChemAxon
Polarizability	53.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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]+	211.038	31661259
DarkChem	[M-H]-	205.534	31661259
DeepCCS	[M-2H]-	244.446	30932474
DeepCCS	[M+Na]+	220.809	30932474
AllCCS	[M+H]+	215.0	32859911
AllCCS	[M+H-H2O]+	213.2	32859911
AllCCS	[M+NH4]+	216.6	32859911
AllCCS	[M+Na]+	217.0	32859911
AllCCS	[M-H]-	218.6	32859911
AllCCS	[M+Na-2H]-	220.7	32859911
AllCCS	[M+HCOO]-	223.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.44 minutes	32390414
Predicted by Siyang on May 30, 2022	24.8557 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4032.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	614.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	270.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	224.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	498.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1376.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1729.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1907.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	763.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2384.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	763.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	820.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	520.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	535.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Macrocarpal I	CC(C)CC(C1CCC(C)(O)C2CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O	3601.2	Standard polar	33892256
Macrocarpal I	CC(C)CC(C1CCC(C)(O)C2CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O	3322.7	Standard non polar	33892256
Macrocarpal I	CC(C)CC(C1CCC(C)(O)C2CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O	3882.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Macrocarpal I,1TMS,isomer #1	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3771.8	Semi standard non polar	33892256
Macrocarpal I,1TMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3844.1	Semi standard non polar	33892256
Macrocarpal I,1TMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	3912.7	Semi standard non polar	33892256
Macrocarpal I,1TMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	3915.9	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #1	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3740.6	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3742.0	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3649.5	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3816.3	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #5	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3818.5	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #6	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	3904.1	Semi standard non polar	33892256
Macrocarpal I,2TMS,isomer #7	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	3906.5	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #1	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3726.7	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3728.0	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3625.3	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3625.8	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #5	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3812.5	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #6	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3809.0	Semi standard non polar	33892256
Macrocarpal I,3TMS,isomer #7	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	3892.0	Semi standard non polar	33892256
Macrocarpal I,4TMS,isomer #1	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O)CCC12C	3723.1	Semi standard non polar	33892256
Macrocarpal I,4TMS,isomer #2	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3650.2	Semi standard non polar	33892256
Macrocarpal I,4TMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3642.1	Semi standard non polar	33892256
Macrocarpal I,4TMS,isomer #4	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3798.6	Semi standard non polar	33892256
Macrocarpal I,5TMS,isomer #1	CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)(O[Si](C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C)CCC12C	3679.5	Semi standard non polar	33892256
Macrocarpal I,1TBDMS,isomer #1	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O)CCC12C	4000.8	Semi standard non polar	33892256
Macrocarpal I,1TBDMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4073.9	Semi standard non polar	33892256
Macrocarpal I,1TBDMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	4145.6	Semi standard non polar	33892256
Macrocarpal I,1TBDMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	4148.0	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #1	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O)CCC12C	4241.3	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O)CCC12C	4248.1	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4165.7	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4308.6	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #5	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4317.0	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #6	CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	4370.2	Semi standard non polar	33892256
Macrocarpal I,2TBDMS,isomer #7	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	4386.8	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #1	CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O)CCC12C	4421.5	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #2	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O)CCC12C	4438.5	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #3	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4366.0	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #4	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)(O[Si](C)(C)C(C)(C)C)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4383.0	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #5	CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4503.0	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #6	CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC12C	4515.6	Semi standard non polar	33892256
Macrocarpal I,3TBDMS,isomer #7	CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)(O)C2CC(C(C)(C)O)CCC12C	4558.5	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 - Macrocarpal I GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7r-5121900000-53c85ac6146839513098	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal I GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-7105089000-b84297b419706dab6fb1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal I GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal I GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal I GC-MS ("Macrocarpal I,3TBDMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - Macrocarpal I 10V, Positive-QTOF	splash10-00dl-0000900000-071e025f7d3c81c9fbbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 20V, Positive-QTOF	splash10-0ac0-1020900000-cb9579c1e951e4f56823	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 40V, Positive-QTOF	splash10-0a4i-7076900000-8610ad7ce8a44c221748	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 10V, Negative-QTOF	splash10-000i-0000900000-5f981f9f49f9d7bd4a91	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 20V, Negative-QTOF	splash10-023c-0100900000-20a27a186e0d39fdf5c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 40V, Negative-QTOF	splash10-0006-2424900000-5c32c2cd115bc4529c75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 10V, Positive-QTOF	splash10-01bc-0000900000-b9d1eccde1565007dcd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 20V, Positive-QTOF	splash10-00r2-0140900000-2f7e02d87387ca529857	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 40V, Positive-QTOF	splash10-00lb-2910000000-0cea0ee97861ad929733	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 10V, Negative-QTOF	splash10-000i-0000900000-c50e39f74db4ba66e11b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 20V, Negative-QTOF	splash10-000i-0400900000-05ad2508cc639109b62d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal I 40V, Negative-QTOF	splash10-0006-9743600000-bc2c374955451e0fc912	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

FDB021580

KNApSAcK ID

Not Available

Chemspider ID

29814538

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56776316

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1893591

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 Macrocarpal I (HMDB0041587)

MOL for HMDB0041587 (Macrocarpal I)

3D MOL for HMDB0041587 (Macrocarpal I)

3D SDF for HMDB0041587 (Macrocarpal I)

3D-SDF for HMDB0041587 (Macrocarpal I)

PDB for HMDB0041587 (Macrocarpal I)

3D PDB for HMDB0041587 (Macrocarpal I)

SMILES for HMDB0041587 (Macrocarpal I)

INCHI for HMDB0041587 (Macrocarpal I)

Structure for HMDB0041587 (Macrocarpal I)

3D Structure for HMDB0041587 (Macrocarpal I)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra