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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:07:33 UTC

Update Date

2022-03-07 02:56:17 UTC

HMDB ID

HMDB0039621

Secondary Accession Numbers

HMDB39621

Metabolite Identification

Common Name

beta-Santalic acid

Description

beta-Santalic acid, also known as b-santalate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on beta-Santalic acid.

Structure

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

HMDB0039621
     RDKit          3D
beta-Santalic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.0039    0.8048   -2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808    0.2675   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.2796   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7290    0.8045   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    0.9402    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.1975    1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -1.2055    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.0976    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    1.3540    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -1.0407    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -1.0806   -0.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    0.0586   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -0.0894    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    1.2207    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263   -1.3109    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -1.1984    0.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -2.5657    0.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024    1.2124   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8526   -3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441   -0.7306   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.4619   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.7382   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    1.9403    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.7816    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418   -0.5353    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985   -1.3226    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647   -2.1284    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    2.0887    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392    1.7678    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.1477    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.0514    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -0.9305    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.0749   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733   -1.0099   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406    1.0539   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503    0.9421    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727    1.6968    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9416    1.8264   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513   -3.3065   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  8  2  1  0
  7  3  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
M  END


  Mrv0541 02241208042D          

 17 18  0  0  0  0            999 V2000
    0.4791    1.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433    1.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599    1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791    2.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -0.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599   -1.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -1.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579   -1.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579   -2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    2.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    1.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    1.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745    0.4053    0.0000 C   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
  2 16  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039621

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(=C\CCC1(C)C2CCC(C2)C1=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10(14(16)17)5-4-8-15(3)11(2)12-6-7-13(15)9-12/h5,12-13H,2,4,6-9H2,1,3H3,(H,16,17)/b10-5-

> <INCHI_KEY>
PMCPDNGTLRPFQQ-YHYXMXQVSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.370785403285453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-methyl-5-{2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl}pent-2-enoic acid

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
3.7110019906666674

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.058315117279646

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.1696

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-methyl-5-{2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl}pent-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0039621
     RDKit          3D
beta-Santalic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.0039    0.8048   -2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808    0.2675   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.2796   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7290    0.8045   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    0.9402    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.1975    1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -1.2055    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.0976    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    1.3540    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -1.0407    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -1.0806   -0.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    0.0586   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -0.0894    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    1.2207    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263   -1.3109    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -1.1984    0.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -2.5657    0.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024    1.2124   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8526   -3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441   -0.7306   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.4619   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.7382   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    1.9403    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.7816    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418   -0.5353    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985   -1.3226    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647   -2.1284    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    2.0887    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392    1.7678    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.1477    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.0514    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -0.9305    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.0749   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733   -1.0099   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406    1.0539   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503    0.9421    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727    1.6968    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9416    1.8264   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513   -3.3065   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  8  2  1  0
  7  3  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  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       0.894   3.375   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.134   2.548   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.098   3.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.410   5.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.894   4.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.757   1.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.757  -0.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.997  -1.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.860  -2.823   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.098  -3.649   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.894  -2.685   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.481  -3.512   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.481  -5.027   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.860   3.787   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.344   3.512   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.481   1.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.446   0.757   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4   15                                                  
CONECT    6    7   16                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    9   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    5   14   16                                                  
CONECT   16    2    6   15   17                                             
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0039621
HETATM    1  C1  UNL     1      -1.004   0.805  -2.126  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.481   0.268  -1.008  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.877  -0.280  -0.934  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.729   0.805  -0.317  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.043   0.940   1.054  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.066  -0.198   1.160  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.770  -1.205   0.275  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.814   0.098   0.309  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.146   1.354   0.830  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.123  -1.041   0.409  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.286  -1.081  -0.548  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.191   0.059  -0.435  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.418  -0.089   0.025  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.197   1.221   0.060  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.026  -1.311   0.481  1.00  0.00           C  
HETATM   16  O1  UNL     1       5.243  -1.198   0.878  1.00  0.00           O  
HETATM   17  O2  UNL     1       3.520  -2.566   0.561  1.00  0.00           O  
HETATM   18  H1  UNL     1      -0.002   1.212  -2.226  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.631   0.853  -3.010  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.244  -0.731  -1.826  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.762   0.462  -0.136  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.740   1.738  -0.874  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.631   1.940   1.076  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.798   0.782   1.877  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.842  -0.535   2.152  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.798  -1.323   0.700  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.265  -2.128   0.082  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.102   2.089   0.031  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.739   1.768   1.715  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.833   1.148   1.314  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.334  -2.051   0.498  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.625  -0.931   1.433  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.725  -2.075  -0.528  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.873  -1.010  -1.618  1.00  0.00           H  
HETATM   35  H18 UNL     1       1.841   1.054  -0.764  1.00  0.00           H  
HETATM   36  H19 UNL     1       5.250   0.942   0.119  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.873   1.697   1.026  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.942   1.826  -0.820  1.00  0.00           H  
HETATM   39  H22 UNL     1       3.851  -3.307  -0.039  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    8
CONECT    3    4    7   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    8   25
CONECT    7   26   27
CONECT    8    9   10
CONECT    9   28   29   30
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   13   35
CONECT   13   14   15
CONECT   14   36   37   38
CONECT   15   16   16   17
CONECT   17   39
END

HMDB0039621
     RDKit          3D
beta-Santalic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.0039    0.8048   -2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808    0.2675   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.2796   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7290    0.8045   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    0.9402    1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.1975    1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -1.2055    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    0.0976    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    1.3540    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -1.0407    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -1.0806   -0.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914    0.0586   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -0.0894    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    1.2207    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263   -1.3109    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -1.1984    0.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200   -2.5657    0.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0024    1.2124   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8526   -3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441   -0.7306   -1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.4619   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.7382   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    1.9403    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.7816    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418   -0.5353    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985   -1.3226    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647   -2.1284    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    2.0887    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392    1.7678    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    1.1477    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.0514    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -0.9305    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.0749   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733   -1.0099   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406    1.0539   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503    0.9421    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727    1.6968    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9416    1.8264   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513   -3.3065   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  8  2  1  0
  7  3  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Santalate	Generator
b-Santalic acid	Generator
beta-Santalate	Generator
Β-santalate	Generator
Β-santalic acid	Generator
b-Santala-3(15),10-dien-12-Oic acid	HMDB
(2Z)-2-Methyl-5-{2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl}pent-2-enoate	Generator

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

(2Z)-2-methyl-5-{2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl}pent-2-enoic acid

Traditional Name

(2Z)-2-methyl-5-{2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl}pent-2-enoic acid

CAS Registry Number

73590-17-7

SMILES

C\C(=C\CCC1(C)C2CCC(C2)C1=C)C(O)=O

InChI Identifier

InChI=1S/C15H22O2/c1-10(14(16)17)5-4-8-15(3)11(2)12-6-7-13(15)9-12/h5,12-13H,2,4,6-9H2,1,3H3,(H,16,17)/b10-5-

InChI Key

PMCPDNGTLRPFQQ-YHYXMXQVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0039621)
Cell membrane (HMDB: HMDB0039621)

Cellular substructure

Extracellular (HMDB: HMDB0039621)
Membrane (HMDB: HMDB0039621)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039621)

Source

Endogenous

Endogenous (HMDB: HMDB0039621)

Animal

Animal (HMDB: HMDB0039621)

Exogenous

Food

Food (HMDB: HMDB0039621)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039621)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039621)

Cellular process

Cell signaling (HMDB: HMDB0039621)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039621)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039621)

Nutrient

Nutrient (HMDB: HMDB0039621)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039621)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0039621)

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	0.015 g/L	ALOGPS
logP	4.49	ALOGPS
logP	3.71	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.06	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.17 m³·mol⁻¹	ChemAxon
Polarizability	27.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.921	31661259
DarkChem	[M-H]-	150.02	31661259
DeepCCS	[M+H]+	160.571	30932474
DeepCCS	[M-H]-	158.213	30932474
DeepCCS	[M-2H]-	191.099	30932474
DeepCCS	[M+Na]+	166.665	30932474
AllCCS	[M+H]+	157.0	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.3	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Santalic acid	C\C(=C\CCC1(C)C2CCC(C2)C1=C)C(O)=O	2940.0	Standard polar	33892256
beta-Santalic acid	C\C(=C\CCC1(C)C2CCC(C2)C1=C)C(O)=O	1784.7	Standard non polar	33892256
beta-Santalic acid	C\C(=C\CCC1(C)C2CCC(C2)C1=C)C(O)=O	1885.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Santalic acid,1TMS,isomer #1	C=C1C2CCC(C2)C1(C)CC/C=C(/C)C(=O)O[Si](C)(C)C	1869.8	Semi standard non polar	33892256
beta-Santalic acid,1TBDMS,isomer #1	C=C1C2CCC(C2)C1(C)CC/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C	2100.9	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 - beta-Santalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9440000000-73245a62f30fc93ea33f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Santalic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0096-9360000000-583d410d2dfa82bc1d25	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Santalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Santalic acid 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 - beta-Santalic acid 10V, Positive-QTOF	splash10-000i-1690000000-0048f7ca1b60ae56fba6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 20V, Positive-QTOF	splash10-01p9-3910000000-33c32ff59f1edb3e95d8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 40V, Positive-QTOF	splash10-0gb9-9300000000-1e1631df178b0c1108ca	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 10V, Negative-QTOF	splash10-001i-0190000000-a6e5c65565d1f19657ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 20V, Negative-QTOF	splash10-001r-1970000000-7466957ad455d3b6f33e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 40V, Negative-QTOF	splash10-00di-5910000000-afd7baf56516e1b5877b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 10V, Negative-QTOF	splash10-001i-0390000000-4c938725f6ee9864c142	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 20V, Negative-QTOF	splash10-03di-0910000000-ed1d1223bc0d2ac03eea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 40V, Negative-QTOF	splash10-02t9-0900000000-01f9afcb647169063640	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 10V, Positive-QTOF	splash10-014i-9510000000-66358136ba2efb432da0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 20V, Positive-QTOF	splash10-01c0-5910000000-7f8c24eb09321a000479	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Santalic acid 40V, Positive-QTOF	splash10-014l-9100000000-057e4f0fd9ac73b070ad	2021-09-25	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

FDB019249

KNApSAcK ID

C00057526

Chemspider ID

35014836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752692

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 beta-Santalic acid (HMDB0039621)

MOL for HMDB0039621 (beta-Santalic acid)

3D MOL for HMDB0039621 (beta-Santalic acid)

3D SDF for HMDB0039621 (beta-Santalic acid)

3D-SDF for HMDB0039621 (beta-Santalic acid)

PDB for HMDB0039621 (beta-Santalic acid)

3D PDB for HMDB0039621 (beta-Santalic acid)

SMILES for HMDB0039621 (beta-Santalic acid)

INCHI for HMDB0039621 (beta-Santalic acid)

Structure for HMDB0039621 (beta-Santalic acid)

3D Structure for HMDB0039621 (beta-Santalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra