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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:39:08 UTC

HMDB ID

HMDB0000949

Secondary Accession Numbers

HMDB00949

Metabolite Identification

Common Name

Tetrahydrocortisol

Description

Taurochenodesoxycholic acid, also known as chenodeoxycholoyltaurine or taurine chenodeoxycholate, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurochenodesoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231218502D          

 26 29  0  0  1  0            999 V2000
    9.3003  -10.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3222   -9.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9410  -12.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6697  -11.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8430  -11.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2028  -11.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5717  -10.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7111  -10.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5129  -12.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7577   -9.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6576   -9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417  -11.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8136  -11.8712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6990  -11.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4277  -10.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290   -9.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8826   -9.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997  -10.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2710  -11.0976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4571   -9.9372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2503   -9.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8004  -10.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0849  -12.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3297   -9.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7399   -8.3679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1076   -8.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  1  0  0  0
 20  2  1  1  0  0  0
  3 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4 14  1  0  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  6 15  1  0  0  0  0
  6  8  1  0  0  0  0
  7 19  1  0  0  0  0
  8 21  1  0  0  0  0
  9 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 22  1  0  0  0  0
 12 19  1  0  0  0  0
 13 23  1  6  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 24  1  1  0  0  0
 16 18  1  0  0  0  0
 21 17  1  0  0  0  0
 17 25  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 26  1  6  0  0  0
M  END


  Mrv0541 02231218502D          

 26 29  0  0  1  0            999 V2000
    9.3003  -10.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3222   -9.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9410  -12.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6697  -11.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8430  -11.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2028  -11.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5717  -10.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7111  -10.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5129  -12.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7577   -9.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6576   -9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417  -11.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8136  -11.8712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6990  -11.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4277  -10.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290   -9.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8826   -9.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997  -10.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2710  -11.0976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4571   -9.9372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2503   -9.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8004  -10.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0849  -12.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3297   -9.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7399   -8.3679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1076   -8.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  1  0  0  0
 20  2  1  1  0  0  0
  3 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4 14  1  0  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  6 15  1  0  0  0  0
  6  8  1  0  0  0  0
  7 19  1  0  0  0  0
  8 21  1  0  0  0  0
  9 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 22  1  0  0  0  0
 12 19  1  0  0  0  0
 13 23  1  6  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 24  1  1  0  0  0
 16 18  1  0  0  0  0
 21 17  1  0  0  0  0
 17 25  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 26  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000949

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12?,13-,14?,15?,16+,18?,19+,20+,21+/m1/s1

> <INCHI_KEY>
AODPIQQILQLWGS-OBRSLYEHSA-N

> <FORMULA>
C21H34O5

> <MOLECULAR_WEIGHT>
366.4917

> <EXACT_MASS>
366.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.89070801334035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.1134999679999997

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.866131690656431

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.584777685879395

> <JCHEM_PKA_STRONGEST_BASIC>
-1.356956600538469

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
97.60139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/C%5BC@%5D12C%5BC@H%5D(O)C3C(CCC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:59})
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.7460    0.3022   -1.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7567   -0.1061    0.2352 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1520    0.9999    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    1.2968    0.5089 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7233    2.0642    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134    1.7782   -0.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    0.0475    0.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4456   -1.1102   -0.2477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3390   -2.3489   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -2.0432   -0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626   -0.8859   -0.0727 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7159   -0.5809   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    0.5744    0.0286 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3517    0.7915   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805    0.2097    1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952    1.8154   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    1.5111    0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.3547   -0.1464 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2537    0.7450   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -1.3741    0.4353 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7597   -2.4582   -0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -2.0898    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1528   -0.5771    0.6299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3676   -0.3726    2.0277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972    0.1554   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5731   -0.2949   -1.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7726    1.4495    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7356    1.9467   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204    0.3040   -1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387   -0.4071   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712    1.3004   -1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7738    1.8932    1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    0.6731    2.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077    2.5893   -0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009   -0.2597    1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922   -0.8323   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -2.6234    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624   -3.1747   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -2.9266   -0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5420   -1.7668   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119   -1.1623    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3511   -1.4651   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669   -0.3021   -1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    0.8966    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9730    2.6392    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466    2.0926   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903    1.2343    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5065    2.3954    0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.7513   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    0.0236   -2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    1.7382   -1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.5684    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067   -2.4080   -1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -3.4467    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9166   -2.2859   -0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -2.6642    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -0.6906    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2539    1.2757    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9728    2.1802    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1479    2.7795   -0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 20  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6 34  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  7 35  1  1  0  0  0
  8  9  1  0  0  0  0
  8 20  1  0  0  0  0
  8 36  1  6  0  0  0
  9 10  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 10 11  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 11 41  1  1  0  0  0
 12 13  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 44  1  0  0  0  0
 16 17  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 18  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 19  1  6  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 20 21  1  0  0  0  0
 20 52  1  1  0  0  0
 21 22  1  0  0  0  0
 21 53  1  0  0  0  0
 21 54  1  0  0  0  0
 22 23  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 24 57  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 28 60  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      17.361 -19.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.135 -16.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.557 -23.071   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.917 -22.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.640 -20.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.779 -20.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.001 -19.898   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.727 -19.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.891 -22.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.081 -17.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.494 -17.664   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.251 -22.254   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.585 -22.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.971 -20.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.332 -20.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.721 -18.454   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.048 -17.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.666 -19.993   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.306 -20.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.387 -18.549   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.867 -18.126   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      25.761 -19.181   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.225 -22.882   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      17.415 -17.638   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      23.781 -15.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      22.601 -16.609   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   12    4                                                       
CONECT    4    3   14                                                       
CONECT    5    7   13                                                       
CONECT    6   15    8                                                       
CONECT    7    5   19                                                       
CONECT    8    6   21                                                       
CONECT    9   13   12                                                       
CONECT   10   20   16                                                       
CONECT   11   17   22                                                       
CONECT   12    3    9   19                                                  
CONECT   13    5    9   23                                                  
CONECT   14    4   15   18                                                  
CONECT   15    6   14   20                                                  
CONECT   16   10   24   18                                                  
CONECT   17   11   21   25                                                  
CONECT   18   14   16   19                                                  
CONECT   19    1    7   12   18                                             
CONECT   20    2   10   15   21                                             
CONECT   21    8   17   20   26                                             
CONECT   22   11                                                            
CONECT   23   13                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5BC@%5D12C%5BC@H%5D(O)C3C(CCC... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      -1.746   0.302  -1.239  1.00  0.00           C  
HETATM    2  C   UNL     1      -1.757  -0.106   0.235  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.152   1.000   1.078  1.00  0.00           C  
HETATM    4  C   UNL     1       0.246   1.297   0.509  1.00  0.00           C  
HETATM    5  H   UNL     1       0.723   2.064   1.118  1.00  0.00           H  
HETATM    6  O   UNL     1       0.113   1.778  -0.830  1.00  0.00           O  
HETATM    7  C   UNL     1       1.120   0.048   0.504  1.00  0.00           C  
HETATM    8  C   UNL     1       0.446  -1.110  -0.248  1.00  0.00           C  
HETATM    9  C   UNL     1       1.339  -2.349  -0.169  1.00  0.00           C  
HETATM   10  C   UNL     1       2.692  -2.043  -0.815  1.00  0.00           C  
HETATM   11  C   UNL     1       3.363  -0.886  -0.073  1.00  0.00           C  
HETATM   12  C   UNL     1       4.716  -0.581  -0.717  1.00  0.00           C  
HETATM   13  C   UNL     1       5.387   0.574   0.029  1.00  0.00           C  
HETATM   14  H   UNL     1       6.352   0.791  -0.430  1.00  0.00           H  
HETATM   15  O   UNL     1       5.580   0.210   1.397  1.00  0.00           O  
HETATM   16  C   UNL     1       4.495   1.815  -0.048  1.00  0.00           C  
HETATM   17  C   UNL     1       3.142   1.511   0.597  1.00  0.00           C  
HETATM   18  C   UNL     1       2.470   0.355  -0.146  1.00  0.00           C  
HETATM   19  C   UNL     1       2.254   0.745  -1.610  1.00  0.00           C  
HETATM   20  C   UNL     1      -0.883  -1.374   0.435  1.00  0.00           C  
HETATM   21  C   UNL     1      -1.760  -2.458  -0.201  1.00  0.00           C  
HETATM   22  C   UNL     1      -3.184  -2.090   0.298  1.00  0.00           C  
HETATM   23  C   UNL     1      -3.153  -0.577   0.630  1.00  0.00           C  
HETATM   24  O   UNL     1      -3.368  -0.373   2.028  1.00  0.00           O  
HETATM   25  C   UNL     1      -4.197   0.155  -0.173  1.00  0.00           C  
HETATM   26  O   UNL     1      -4.573  -0.295  -1.228  1.00  0.00           O  
HETATM   27  C   UNL     1      -4.773   1.450   0.343  1.00  0.00           C  
HETATM   28  O   UNL     1      -5.736   1.947  -0.589  1.00  0.00           O  
HETATM   29  H   UNL     1      -0.720   0.304  -1.608  1.00  0.00           H  
HETATM   30  H   UNL     1      -2.339  -0.407  -1.817  1.00  0.00           H  
HETATM   31  H   UNL     1      -2.171   1.300  -1.343  1.00  0.00           H  
HETATM   32  H   UNL     1      -1.774   1.893   1.018  1.00  0.00           H  
HETATM   33  H   UNL     1      -1.069   0.673   2.114  1.00  0.00           H  
HETATM   34  H   UNL     1      -0.408   2.589  -0.907  1.00  0.00           H  
HETATM   35  H   UNL     1       1.301  -0.260   1.534  1.00  0.00           H  
HETATM   36  H   UNL     1       0.292  -0.832  -1.290  1.00  0.00           H  
HETATM   37  H   UNL     1       1.489  -2.623   0.875  1.00  0.00           H  
HETATM   38  H   UNL     1       0.862  -3.175  -0.697  1.00  0.00           H  
HETATM   39  H   UNL     1       3.328  -2.927  -0.761  1.00  0.00           H  
HETATM   40  H   UNL     1       2.542  -1.767  -1.859  1.00  0.00           H  
HETATM   41  H   UNL     1       3.512  -1.162   0.971  1.00  0.00           H  
HETATM   42  H   UNL     1       5.351  -1.465  -0.665  1.00  0.00           H  
HETATM   43  H   UNL     1       4.567  -0.302  -1.760  1.00  0.00           H  
HETATM   44  H   UNL     1       6.002   0.897   1.931  1.00  0.00           H  
HETATM   45  H   UNL     1       4.973   2.639   0.483  1.00  0.00           H  
HETATM   46  H   UNL     1       4.347   2.093  -1.091  1.00  0.00           H  
HETATM   47  H   UNL     1       3.290   1.234   1.641  1.00  0.00           H  
HETATM   48  H   UNL     1       2.506   2.395   0.543  1.00  0.00           H  
HETATM   49  H   UNL     1       3.212   0.751  -2.129  1.00  0.00           H  
HETATM   50  H   UNL     1       1.588   0.024  -2.084  1.00  0.00           H  
HETATM   51  H   UNL     1       1.807   1.738  -1.659  1.00  0.00           H  
HETATM   52  H   UNL     1      -0.731  -1.568   1.497  1.00  0.00           H  
HETATM   53  H   UNL     1      -1.707  -2.408  -1.288  1.00  0.00           H  
HETATM   54  H   UNL     1      -1.470  -3.447   0.155  1.00  0.00           H  
HETATM   55  H   UNL     1      -3.917  -2.286  -0.485  1.00  0.00           H  
HETATM   56  H   UNL     1      -3.428  -2.664   1.191  1.00  0.00           H  
HETATM   57  H   UNL     1      -4.224  -0.691   2.345  1.00  0.00           H  
HETATM   58  H   UNL     1      -5.254   1.276   1.305  1.00  0.00           H  
HETATM   59  H   UNL     1      -3.973   2.180   0.463  1.00  0.00           H  
HETATM   60  H   UNL     1      -6.148   2.780  -0.322  1.00  0.00           H  
CONECT    1    2   29   30   31                                       
CONECT    2    1    3   20   23                                       
CONECT    3    2    4   32   33                                       
CONECT    4    3    5    6    7                                       
CONECT    5    4                                                      
CONECT    6    4   34                                                 
CONECT    7    4    8   18   35                                       
CONECT    8    7    9   20   36                                       
CONECT    9    8   10   37   38                                       
CONECT   10    9   11   39   40                                       
CONECT   11   10   12   18   41                                       
CONECT   12   11   13   42   43                                       
CONECT   13   12   14   15   16                                       
CONECT   14   13                                                      
CONECT   15   13   44                                                 
CONECT   16   13   17   45   46                                       
CONECT   17   16   18   47   48                                       
CONECT   18   17    7   11   19                                       
CONECT   19   18   49   50   51                                       
CONECT   20    8    2   21   52                                       
CONECT   21   20   22   53   54                                       
CONECT   22   21   23   55   56                                       
CONECT   23   22    2   24   25                                       
CONECT   24   23   57                                                 
CONECT   25   23   26   26   27                                       
CONECT   26   25   25                                                 
CONECT   27   25   28   58   59                                       
CONECT   28   27   60                                                 
CONECT   29    1                                                      
CONECT   30    1                                                      
CONECT   31    1                                                      
CONECT   32    3                                                      
CONECT   33    3                                                      
CONECT   34    6                                                      
CONECT   35    7                                                      
CONECT   36    8                                                      
CONECT   37    9                                                      
CONECT   38    9                                                      
CONECT   39   10                                                      
CONECT   40   10                                                      
CONECT   41   11                                                      
CONECT   42   12                                                      
CONECT   43   12                                                      
CONECT   44   15                                                      
CONECT   45   16                                                      
CONECT   46   16                                                      
CONECT   47   17                                                      
CONECT   48   17                                                      
CONECT   49   19                                                      
CONECT   50   19                                                      
CONECT   51   19                                                      
CONECT   52   20                                                      
CONECT   53   21                                                      
CONECT   54   21                                                      
CONECT   55   22                                                      
CONECT   56   22                                                      
CONECT   57   24                                                      
CONECT   58   27                                                      
CONECT   59   27                                                      
CONECT   60   28                                                      
MASTER        0    0    0    0    0    0    0    0   60    0   60    0
END

https://cactus.nci.nih.gov/chemical/structure/C%5BC@%5D12C%5BC@H%5D(O)C3C(CCC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:59})
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 28 60  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
Taurochenodeoxycholic acid	Kegg
Chenodeoxycholoyltaurine	Kegg
Taurochenodeoxycholate	Generator
Taurochenodesoxycholate	Generator
Taurine chenodeoxycholate	HMDB
Taurine chenodeoxycholic acid	HMDB
12-Deoxycholyltaurine	HMDB
12-Desoxycholyltaurine	HMDB
3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide	HMDB
Chenodeoxycholyltaurine	HMDB
Chenyltaurine	HMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurine	HMDB
Acid, taurochenodeoxycholic	HMDB
Chenodeoxycholate, taurine	HMDB
2-Hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone	HMDB
3a,11b,17,21-Tetrahydroxy-5b-pregnan-20-one	HMDB
3b,11b,17,21-Tetrahydroxy-5b-pregnan-20-one	HMDB
3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-ON	HMDB
5b-Tetrahydrocortisol	HMDB
Dihydrocortison	HMDB
tetrahydro-Cortisol	HMDB
Urocortisol	HMDB

Chemical Formula

C₂₁H₃₄O₅

Average Molecular Weight

366.4917

Monoisotopic Molecular Weight

366.240624198

IUPAC Name

2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

Traditional Name

2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone

CAS Registry Number

53-02-1

SMILES

C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO

InChI Identifier

InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12?,13-,14?,15?,16+,18?,19+,20+,21+/m1/s1

InChI Key

AODPIQQILQLWGS-OBRSLYEHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

Substituents

Taurinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Fatty acyl
Fatty amide
N-acyl-amine
Alkanesulfonic acid
Cyclic alcohol
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid taurine conjugate (CHEBI:16525 )
C26 bile acids, alcohols, and derivatives (C05465 )
Taurine conjugates (C05465 )
Taurine conjugates (LMST05040005 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Industrial application:

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.6 m³·mol⁻¹	ChemAxon
Polarizability	40.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-3539000000-bf3e8ad7a2d21593e681	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0fe3-1311189000-3a0cfdea998a0531cb8b	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000j-3539000000-bf3e8ad7a2d21593e681	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0019000000-5967aef805edb472d5a5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0532-0059000000-6e3db383f9bda6aa194a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-1492000000-2266b6b18ef46f0eec05	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-5471dbe684b873e5784d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ap1-2039000000-d95c86b33b8f11b83354	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9086000000-0e28c8ffdf44e3e921fe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-31730eb1a915ec83558e	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1926000000-49f68aeefa3e0ecff93e	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mk-4930000000-ad7e5d12918fff3d0452	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0009000000-599710d9e5fe39c6c2e8	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066r-5009000000-934cc72c238c468a325b	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-1079000000-515731aac544f36e01c8	2021-09-07	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.19 (0.18-0.24) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11085621	details
Urine	Detected and Quantified	0.14 (0.086-0.17) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11085621	details
Urine	Detected and Quantified	0.21 +/- 0.038 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15560936	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.20 +/- 0.023 umol/mmol creatinine	Adult (>18 years old)	Female	Eating disorder	15560936	details
Urine	Detected and Quantified	0.62 +/- 0.085 umol/mmol creatinine	Adult (>18 years old)	Female	Eating disorder	15560936	details
Urine	Detected and Quantified	0.00024 +/- 0.00020 umol/mmol creatinine	Adult (>18 years old)	Female	Stress urinary incontinence	12707870	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08833

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022335

KNApSAcK ID

Not Available

Chemspider ID

343282

KEGG Compound ID

C05465

BioCyc ID

CHENODEOXYCHOLOYLTAURINE

BiGG ID

45864

Wikipedia Link

Not Available

METLIN ID

5897

PubChem Compound

387316

PDB ID

Not Available

ChEBI ID

16525

Food Biomarker Ontology

Not Available

VMH ID

TDCHOLA

MarkerDB ID

Not Available

References

Synthesis Reference

Gould, David H.; Oliveto, Eugene P. 17a-Hydroxycorticosterone and intermediates. (1957), US 2783254 19570226 CAN 51:62564 AN 1957:62564

Material Safety Data Sheet (MSDS)

Not Available

General References

Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
Weykamp CW, Penders TJ, Schmidt NA, Borburgh AJ, van de Calseyde JF, Wolthers BJ: Steroid profile for urine: reference values. Clin Chem. 1989 Dec;35(12):2281-4. [PubMed:2591044 ]
Kerstens MN, van der Kleij FG, Boonstra AH, Sluiter WJ, van der Molen JC, Navis G, Dullaart RP: Angiotensin administration stimulates renal 11 beta-hydroxysteroid dehydrogenase activity in healthy men. Kidney Int. 2004 Jun;65(6):2065-70. [PubMed:15149319 ]
Koren W, Grienspuhn A, Kuznetsov SR, Berezin M, Rosenthal T, Postnov YV: Enhanced Na+/H+ exchange in Cushing's syndrome reflects functional hypermineralocorticoidism. J Hypertens. 1998 Aug;16(8):1187-91. [PubMed:9794723 ]
Quinkler M, Zehnder D, Lepenies J, Petrelli MD, Moore JS, Hughes SV, Cockwell P, Hewison M, Stewart PM: Expression of renal 11beta-hydroxysteroid dehydrogenase type 2 is decreased in patients with impaired renal function. Eur J Endocrinol. 2005 Aug;153(2):291-9. [PubMed:16061836 ]
Rosler A, Leiberman E, Rosenmann A, Ben-Uzilio R, Weidenfeld J: Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1979 Oct;49(4):546-51. [PubMed:314453 ]
Rapetti S, Francia G, Iacono C, Martignoni G, Contessi G, Brunelli M, Galvanin F, Serio G: An unusual case of Cushing's syndrome due to ACTH-independent macronodular adrenal hyperplasia. Chir Ital. 2003 Mar-Apr;55(2):235-41. [PubMed:12744099 ]
Melander O, Frandsen E, Groop L, Hulthen UL: No evidence of a relation between 11beta-hydroxysteroid dehydrogenase type 2 activity and salt sensitivity. Am J Hypertens. 2003 Sep;16(9 Pt 1):729-33. [PubMed:12944030 ]
Panin LE, Tuzikov FV, Gimautdinova OI: Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):309-18. [PubMed:14698212 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

Tetrahydrocortisol + NAD → Dihydrocortisol + NADH + Hydrogen Ion	details
Tetrahydrocortisol + NADP → Dihydrocortisol + NADPH + Hydrogen Ion	details

Showing metabocard for Tetrahydrocortisol (HMDB0000949)

MOL for HMDB0000949 (Tetrahydrocortisol)

3D MOL for HMDB0000949 (Tetrahydrocortisol)

3D SDF for HMDB0000949 (Tetrahydrocortisol)

3D-SDF for HMDB0000949 (Tetrahydrocortisol)

PDB for HMDB0000949 (Tetrahydrocortisol)

3D PDB for HMDB0000949 (Tetrahydrocortisol)

SMILES for HMDB0000949 (Tetrahydrocortisol)

INCHI for HMDB0000949 (Tetrahydrocortisol)

Structure for HMDB0000949 (Tetrahydrocortisol)

3D Structure for HMDB0000949 (Tetrahydrocortisol)

GC-MS

LC-MS/MS

Enzymes

Reactions