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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (8) Show 9 proteins XML

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:58 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002586

Secondary Accession Numbers

HMDB02586

Metabolite Identification

Common Name

Chenodeoxycholic acid 3-sulfate

Description

Chenodeoxycholic acid 3-sulfate, also known as chenodeoxycholate sulfate conjugate or CDCS, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Based on a literature review a significant number of articles have been published on Chenodeoxycholic acid 3-sulfate.

Structure

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

7-Sulfocholyltaurine.mol
  Mrv0541 02231219332D          

 36 39  0  0  0  0            999 V2000
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M  END

HMDB0002586
     RDKit          3D
Chenodeoxycholic acid 3-sulfate
 72 75  0  0  0  0  0  0  0  0999 V2000
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M  END

7-Sulfocholyltaurine.mol
  Mrv0541 02231219332D          

 36 39  0  0  0  0            999 V2000
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  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  7 27  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 28 29  1  0  0  0  0
  1 28  1  6  0  0  0
  5 33  1  1  0  0  0
 22 34  1  6  0  0  0
  8 35  1  1  0  0  0
  9 36  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002586

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

> <INCHI_KEY>
WHMOBEGYTDWMIG-BSWAIDMHSA-N

> <FORMULA>
C24H40O7S

> <MOLECULAR_WEIGHT>
472.635

> <EXACT_MASS>
472.249474324

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
51.88292797876075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
2.321619271901573

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.595945681139674

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4705842836832614

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5428097932948205

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
119.26559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002586
     RDKit          3D
Chenodeoxycholic acid 3-sulfate
 72 75  0  0  0  0  0  0  0  0999 V2000
   -5.0323    0.9606   -1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1198   -0.0577   -1.0267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9230   -1.2024   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1132   -1.0791    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0656   -0.5241    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351    0.6915    1.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7362   -1.2402    2.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.5792   -0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2232    1.5203    0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    1.7911    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.9196    0.4915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2939    0.3572    1.0331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9764   -0.2996   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1237   -1.4901   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -1.0767   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2745    0.2058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1938   -1.0308    1.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -0.6289    0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5623   -1.6643    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -1.2066   -1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4762   -1.3173   -1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776   -0.0792   -0.7055 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1536    0.3583   -1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6148    0.4775   -0.7956 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.6357   -0.4812    0.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7358    0.1572   -1.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650    2.0193   -0.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524    1.0322   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    0.6315    0.4195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2072    1.8045    0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016    1.3726    1.6785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5108    2.4372    2.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3067    1.6999   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8673    0.4642   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4665    1.5225   -2.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5405   -0.4571   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3628   -1.6412   -1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323   -2.1088   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9766   -0.6354   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5170   -2.1483    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4906   -1.3210    3.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874    1.2319   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    2.4598    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7419    1.1754    1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    2.8939    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    1.6573    2.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    1.3947   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -0.4505    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    0.4161   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5438   -2.0319   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -2.2062    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.5450   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -2.0124   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -2.0382    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2660   -1.2456    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -0.5440    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693   -1.5054    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -2.6655    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -1.7083    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672   -0.5332   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -2.2398   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.5046   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948   -2.2332   -0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.2321    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542    1.9329    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817    1.2735   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631    1.9399   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.4719    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517    2.1312   -0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    2.6309    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    0.8676    2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4462    2.3872    3.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  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  1
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 24 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 16  8  1  0
 29 18  1  0
 16 11  1  0
 31 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  6
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  6
 12 48  1  1
 13 49  1  6
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  1
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  1
 30 69  1  0
 30 70  1  0
 31 71  1  1
 32 72  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7-Sulfocholyltaurine.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.247  -4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.247  -2.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.913  -2.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.913  -5.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.580  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.754  -5.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.088  -4.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.088  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.421  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.886  -2.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.791  -1.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.886  -0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.362   1.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.273   2.523   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.672   4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.159   4.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.868   1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.421  -0.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.421   1.033   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.088   0.263   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.754  -0.507   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.754  -2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.580  -2.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.580  -1.277   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.558   5.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.248   3.320   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.421  -5.127   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.581  -5.127   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0      -5.914  -4.357   0.000  0.00  0.00           S+0
HETATM   30  O   UNK     0      -5.144  -3.023   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.684  -5.690   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.248  -3.587   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      -0.580  -5.897   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.754  -3.587   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.088  -1.277   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.421  -3.587   0.000  0.00  0.00           H+0
CONECT    1    2    4   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   22   35                                             
CONECT    9    8   10   18   36                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   34                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    7                                                            
CONECT   28   29    1                                                       
CONECT   29   30   31   32   28                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33    5                                                            
CONECT   34   22                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0002586
HETATM    1  C1  UNL     1      -5.032   0.961  -1.751  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.120  -0.058  -1.027  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.923  -1.202  -0.631  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.113  -1.079   0.224  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.066  -0.524   1.547  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.335   0.691   1.736  1.00  0.00           O  
HETATM    7  O2  UNL     1      -5.736  -1.240   2.684  1.00  0.00           O  
HETATM    8  C6  UNL     1      -3.074   0.579  -0.295  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.223   1.520   0.817  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.786   1.791   1.331  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.959   0.920   0.491  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.294   0.357   1.033  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.976  -0.300  -0.178  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.124  -1.490  -0.536  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.268  -1.077  -0.869  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.904  -0.275   0.206  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.194  -1.031   1.447  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.398  -0.629   0.077  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.562  -1.664   1.167  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.986  -1.207  -1.185  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.476  -1.317  -1.157  1.00  0.00           C  
HETATM   22  C20 UNL     1       5.178  -0.079  -0.705  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.154   0.358  -1.620  1.00  0.00           O  
HETATM   24  S1  UNL     1       7.615   0.477  -0.796  1.00  0.00           S  
HETATM   25  O4  UNL     1       7.636  -0.481   0.378  1.00  0.00           O  
HETATM   26  O5  UNL     1       8.736   0.157  -1.764  1.00  0.00           O  
HETATM   27  O6  UNL     1       7.865   2.019  -0.189  1.00  0.00           O  
HETATM   28  C21 UNL     1       4.152   1.032  -0.606  1.00  0.00           C  
HETATM   29  C22 UNL     1       3.142   0.632   0.419  1.00  0.00           C  
HETATM   30  C23 UNL     1       2.207   1.805   0.643  1.00  0.00           C  
HETATM   31  C24 UNL     1       1.202   1.373   1.679  1.00  0.00           C  
HETATM   32  O7  UNL     1       0.511   2.437   2.229  1.00  0.00           O  
HETATM   33  H1  UNL     1      -5.307   1.700  -0.973  1.00  0.00           H  
HETATM   34  H2  UNL     1      -5.867   0.464  -2.234  1.00  0.00           H  
HETATM   35  H3  UNL     1      -4.466   1.523  -2.523  1.00  0.00           H  
HETATM   36  H4  UNL     1      -3.540  -0.457  -1.991  1.00  0.00           H  
HETATM   37  H5  UNL     1      -5.363  -1.641  -1.610  1.00  0.00           H  
HETATM   38  H6  UNL     1      -4.332  -2.109  -0.303  1.00  0.00           H  
HETATM   39  H7  UNL     1      -6.977  -0.635  -0.398  1.00  0.00           H  
HETATM   40  H8  UNL     1      -6.517  -2.148   0.342  1.00  0.00           H  
HETATM   41  H9  UNL     1      -6.491  -1.321   3.384  1.00  0.00           H  
HETATM   42  H10 UNL     1      -2.487   1.232  -1.095  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.707   2.460   0.485  1.00  0.00           H  
HETATM   44  H12 UNL     1      -3.742   1.175   1.710  1.00  0.00           H  
HETATM   45  H13 UNL     1      -1.615   2.894   1.155  1.00  0.00           H  
HETATM   46  H14 UNL     1      -1.696   1.657   2.407  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.798   1.395  -0.500  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.103  -0.450   1.761  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.912   0.416  -1.022  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.544  -2.032  -1.427  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.198  -2.206   0.309  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.259  -0.545  -1.829  1.00  0.00           H  
HETATM   53  H21 UNL     1      -1.877  -2.012  -1.001  1.00  0.00           H  
HETATM   54  H22 UNL     1      -1.687  -2.038   1.430  1.00  0.00           H  
HETATM   55  H23 UNL     1      -3.266  -1.246   1.596  1.00  0.00           H  
HETATM   56  H24 UNL     1      -1.815  -0.544   2.372  1.00  0.00           H  
HETATM   57  H25 UNL     1       1.869  -1.505   2.008  1.00  0.00           H  
HETATM   58  H26 UNL     1       2.351  -2.665   0.692  1.00  0.00           H  
HETATM   59  H27 UNL     1       3.622  -1.708   1.475  1.00  0.00           H  
HETATM   60  H28 UNL     1       2.667  -0.533  -2.029  1.00  0.00           H  
HETATM   61  H29 UNL     1       2.583  -2.240  -1.356  1.00  0.00           H  
HETATM   62  H30 UNL     1       4.804  -1.505  -2.221  1.00  0.00           H  
HETATM   63  H31 UNL     1       4.795  -2.233  -0.599  1.00  0.00           H  
HETATM   64  H32 UNL     1       5.601  -0.232   0.296  1.00  0.00           H  
HETATM   65  H33 UNL     1       8.454   1.933   0.604  1.00  0.00           H  
HETATM   66  H34 UNL     1       3.682   1.273  -1.571  1.00  0.00           H  
HETATM   67  H35 UNL     1       4.663   1.940  -0.246  1.00  0.00           H  
HETATM   68  H36 UNL     1       3.684   0.472   1.387  1.00  0.00           H  
HETATM   69  H37 UNL     1       1.752   2.131  -0.308  1.00  0.00           H  
HETATM   70  H38 UNL     1       2.827   2.631   1.039  1.00  0.00           H  
HETATM   71  H39 UNL     1       1.772   0.868   2.484  1.00  0.00           H  
HETATM   72  H40 UNL     1       0.446   2.387   3.217  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    8   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6    6    7
CONECT    7   41
CONECT    8    9   16   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   16   47
CONECT   12   13   31   48
CONECT   13   14   18   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17
CONECT   17   54   55   56
CONECT   18   19   20   29
CONECT   19   57   58   59
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   28   64
CONECT   23   24
CONECT   24   25   25   26   26
CONECT   24   27
CONECT   27   65
CONECT   28   29   66   67
CONECT   29   30   68
CONECT   30   31   69   70
CONECT   31   32   71
CONECT   32   72
END

HMDB0002586
     RDKit          3D
Chenodeoxycholic acid 3-sulfate
 72 75  0  0  0  0  0  0  0  0999 V2000
   -5.0323    0.9606   -1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1198   -0.0577   -1.0267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9230   -1.2024   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1132   -1.0791    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0656   -0.5241    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351    0.6915    1.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7362   -1.2402    2.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.5792   -0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2232    1.5203    0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    1.7911    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.9196    0.4915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2939    0.3572    1.0331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9764   -0.2996   -0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1237   -1.4901   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -1.0767   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2745    0.2058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1938   -1.0308    1.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -0.6289    0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5623   -1.6643    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -1.2066   -1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4762   -1.3173   -1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776   -0.0792   -0.7055 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1536    0.3583   -1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6148    0.4775   -0.7956 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.6357   -0.4812    0.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7358    0.1572   -1.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650    2.0193   -0.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524    1.0322   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    0.6315    0.4195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2072    1.8045    0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016    1.3726    1.6785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5108    2.4372    2.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3067    1.6999   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8673    0.4642   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4665    1.5225   -2.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5405   -0.4571   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3628   -1.6412   -1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323   -2.1088   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9766   -0.6354   -0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5170   -2.1483    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4906   -1.3210    3.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874    1.2319   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    2.4598    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7419    1.1754    1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    2.8939    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    1.6573    2.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    1.3947   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -0.4505    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    0.4161   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5438   -2.0319   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -2.2062    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.5450   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -2.0124   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -2.0382    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2660   -1.2456    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -0.5440    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693   -1.5054    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -2.6655    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -1.7083    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672   -0.5332   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -2.2398   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.5046   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948   -2.2332   -0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.2321    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542    1.9329    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817    1.2735   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631    1.9399   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.4719    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517    2.1312   -0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    2.6309    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    0.8676    2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4462    2.3872    3.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  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  1
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 24 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 16  8  1  0
 29 18  1  0
 16 11  1  0
 31 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  6
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  6
 12 48  1  1
 13 49  1  6
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  1
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  1
 30 69  1  0
 30 70  1  0
 31 71  1  1
 32 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chenodeoxycholate 3-sulfate	Generator
Chenodeoxycholate 3-sulphate	Generator
Chenodeoxycholic acid 3-sulfuric acid	Generator
Chenodeoxycholic acid 3-sulphuric acid	Generator
Chenodeoxycholate sulfate conjugate	MeSH
Chenodeoxycholic acid sulfate conjugate	MeSH
CDCS	MeSH
3-Sulfochenodeoxycholate	HMDB
3-Sulfochenodeoxycholic acid	HMDB
Chenodeoxycholic acid 3-sulphate	HMDB
Chenodeoxycholic acid 3a-sulfate	HMDB
Chenodeoxycholic acid 3a-sulphate	HMDB

Chemical Formula

C₂₄H₄₀O₇S

Average Molecular Weight

472.635

Monoisotopic Molecular Weight

472.249474324

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

59132-32-0

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

WHMOBEGYTDWMIG-BSWAIDMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
Hydroxysteroid
7-hydroxysteroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Cyclic alcohol
Organic sulfuric acid or derivatives
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Sulfates (LMST05020024 )

Ontology

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	206.571	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001891

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0049 g/L	ALOGPS
logP	0.49	ALOGPS
logP	2.32	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.27 m³·mol⁻¹	ChemAxon
Polarizability	51.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	209.256	31661259
DarkChem	[M-H]-	198.745	31661259
DeepCCS	[M-2H]-	250.549	30932474
DeepCCS	[M+Na]+	224.323	30932474
AllCCS	[M+H]+	212.8	32859911
AllCCS	[M+H-H2O]+	211.1	32859911
AllCCS	[M+NH4]+	214.3	32859911
AllCCS	[M+Na]+	214.7	32859911
AllCCS	[M-H]-	207.7	32859911
AllCCS	[M+Na-2H]-	209.6	32859911
AllCCS	[M+HCOO]-	211.9	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.	7.7 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7398 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	65.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3089.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	263.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	615.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	744.4 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	762.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1252.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	587.0 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	1856.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	243.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.5 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	97.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid 3-sulfate	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O	4602.6	Standard polar	33892256
Chenodeoxycholic acid 3-sulfate	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O	3620.5	Standard non polar	33892256
Chenodeoxycholic acid 3-sulfate	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O	3918.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid 3-sulfate,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O	3789.0	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C	3697.0	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O	3809.7	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C	3670.3	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O	3788.0	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3714.5	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3673.8	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	4100.1	Standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	4462.3	Standard polar	33892256
Chenodeoxycholic acid 3-sulfate,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O	4062.5	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3924.9	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4005.8	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4168.6	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4246.8	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,2TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4113.0	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4302.0	Semi standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4941.4	Standard non polar	33892256
Chenodeoxycholic acid 3-sulfate,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4592.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid 3-sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-0667900000-f5e817c86afceff3bc92	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid 3-sulfate GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-4221349000-0993c416b847dc9363a2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid 3-sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid 3-sulfate 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 - Chenodeoxycholic acid 3-sulfate 10V, Positive-QTOF	splash10-0a4i-0002900000-abbbbfd5950c6cf2e226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 20V, Positive-QTOF	splash10-056r-0009200000-087c5d2f48d7160b5dbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 40V, Positive-QTOF	splash10-0a4j-1229200000-7f1303ebc6e2d806539e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 10V, Negative-QTOF	splash10-00di-0001900000-bff4b187cc87bfca1cd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 20V, Negative-QTOF	splash10-00dl-2009400000-eab51a83a4551fd439fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 40V, Negative-QTOF	splash10-0a5a-9007100000-7432e93f953dc907a065	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 10V, Negative-QTOF	splash10-00di-0000900000-29034312137a9db3fb88	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 20V, Negative-QTOF	splash10-00di-1000900000-ade2350b3441a8a2d002	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 40V, Negative-QTOF	splash10-0002-9006400000-0a3dcf516ded28a9a1aa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 10V, Positive-QTOF	splash10-00di-0002900000-06cd8122555b78f76406	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 20V, Positive-QTOF	splash10-0a4i-1019200000-1a2383b307a87525bad2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 3-sulfate 40V, Positive-QTOF	splash10-004i-1589000000-3a790fd1e8a788615b2e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.1 (0.0-1.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected and Quantified	1.06 +/- 1.20 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FDB023031

KNApSAcK ID

Not Available

Chemspider ID

13628372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6719

PubChem Compound

21252312

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

Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
Robben J, Janssen G, Merckx R, Eyssen H: Formation of delta 2- and delta 3-cholenoic acids from bile acid 3-sulfates by a human intestinal Fusobacterium strain. Appl Environ Microbiol. 1989 Nov;55(11):2954-9. [PubMed:2624466 ]

Enzymes

Enzyme Details

1. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Showing metabocard for Chenodeoxycholic acid 3-sulfate (HMDB0002586)

MOL for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

3D MOL for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

3D SDF for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

3D-SDF for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

PDB for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

3D PDB for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

SMILES for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

INCHI for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

Structure for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

3D Structure for HMDB0002586 (Chenodeoxycholic acid 3-sulfate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References