NP-MRD: Showing NP-Card for Taurocholic acid (NP0000461)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:41:56 UTC

NP-MRD ID

NP0000461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taurocholic acid

Description

Taurocholic acid is a bile acid and is the product of the conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.G. Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of taurocholate in fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and sudden intra-uterine death (PMID: 3944741 , 11256973 ).

Structure

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

      
  Mrv1652303182019222D          

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 21  1  1  1  0  0  0
 22  7  1  6  0  0  0
 16 40  1  6  0  0  0
M  END

HMDB0000036
     RDKit          3D
Taurocholic acid
 80 83  0  0  0  0  0  0  0  0999 V2000
    2.1937   -1.0101   -2.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764    0.4177   -2.9166 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0889    1.4137   -2.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973    0.2986   -2.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.7304   -2.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8819    0.3303   -1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7948   -0.7428   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941   -0.5273    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.4742    1.8985 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3108   -0.2567    3.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6575    2.3608   -1.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

      
  Mrv1652303182019222D          

 40 43  0  0  0  0            999 V2000
10001.358110003.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.077910000.1412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2199 9999.7275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.219910002.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.932610000.9746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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10002.144710003.7076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.858610004.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.574210003.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.287810004.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.003410003.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.716910004.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.432410003.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.148010004.1200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10007.560510004.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.735610004.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.863510003.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.287810004.9448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.430110004.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.144710002.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.859010003.2954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.362110000.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  2  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  3  1  1  0  0  0
 13  4  1  1  0  0  0
 17  6  1  6  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  5  1  6  0  0  0
 20  8  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  2  0  0  0  0
 32 35  1  0  0  0  0
 38 39  1  6  0  0  0
 38 25  1  0  0  0  0
 38 21  1  0  0  0  0
 38 24  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21  1  1  1  0  0  0
 22  7  1  6  0  0  0
 16 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

> <INCHI_KEY>
WBWWGRHZICKQGZ-HZAMXZRMSA-N

> <FORMULA>
C26H45NO7S

> <MOLECULAR_WEIGHT>
515.703

> <EXACT_MASS>
515.291673489

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.35935612622693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.2443067183096018

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.402104140110847

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.8802770884096507

> <JCHEM_PKA_STRONGEST_BASIC>
-0.053328131348413965

> <JCHEM_POLAR_SURFACE_AREA>
144.16

> <JCHEM_REFRACTIVITY>
132.19449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000036
     RDKit          3D
Taurocholic acid
 80 83  0  0  0  0  0  0  0  0999 V2000
    2.1937   -1.0101   -2.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764    0.4177   -2.9166 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9289    1.2855   -3.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    1.4137   -2.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973    0.2986   -2.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.7304   -2.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8819    0.3303   -1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7948   -0.7428   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941   -0.5273    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.4742    1.8985 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3108   -0.2567    3.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980    0.6100    1.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7077   -1.9540    1.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    0.9109   -1.6940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6575    2.3608   -1.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230    2.3505   -1.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    1.2677   -0.5047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1763    0.8741   -0.0131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0125   -0.2829    0.9394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1129   -1.3565    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.8552   -0.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9047   -0.2240    0.8229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1601    0.1566   -1.2539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9546   -0.4974   -2.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3427   -0.8398    1.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5943   -2.2185    0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670   -0.9500    2.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6694   -1.3464    3.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8286   -0.5181    2.9724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9823    0.6877    3.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043   -0.3360    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4597    0.0418    0.9210 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2149    1.4932    1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    1.9889    0.8133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0884    2.3776    1.8789 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -1.6592   -2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.3768   -3.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581   -1.2457   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.5469   -3.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    0.7955   -4.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    2.2805   -3.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592    2.2666   -2.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013    1.8101   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657    1.1451   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172   -1.6927   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -0.8500   -1.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3265   -1.3744    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1968    0.4183    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9488   -2.4491    2.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022    0.7802   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327    2.9056   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077    2.8262   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702    3.3311   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440    2.0450   -2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    1.5996    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    0.7049   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    0.1765    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7772   -1.9331    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -2.1316   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -1.7216   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.2072    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632   -1.6163   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641   -0.2705   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6330   -0.3375   -3.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -2.2122   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479   -2.4815    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -2.9794    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263   -1.7528    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -0.0339    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6004   -1.1387    4.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840   -2.4326    3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7594   -1.1102    3.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8602    1.0469    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    0.5111    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2459   -1.2137    0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -0.1425   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    1.6280    2.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0505    2.0530    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737    2.8391    0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    3.1028    1.7073 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  6
 19 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 23 14  1  0
 32 25  1  0
 23 17  1  0
 34 18  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 13 49  1  0
 14 50  1  1
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  6
 19 57  1  1
 20 58  1  0
 20 59  1  0
 21 60  1  6
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  6
 30 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  6
 33 77  1  0
 33 78  1  0
 34 79  1  6
 35 80  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8669.2028673.124   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8661.2128666.930   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8665.2108666.158   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0    8665.2108670.791   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8666.5418668.486   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0    8667.8718673.898   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0    8669.2028668.486   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8667.8718670.791   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8663.8788670.015   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.5448669.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.5448667.704   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.8788666.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2078669.245   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2078667.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.5418666.935   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.8758667.705   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.8728672.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.5388671.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.5388670.032   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.8728669.262   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.2068671.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.2068670.032   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.6708669.556   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.5758670.802   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.6708673.588   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.0038674.357   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8673.3398673.588   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8674.6718674.357   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8676.0068673.588   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8677.3388674.357   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8678.6748673.588   0.000  0.00  0.00           C+0
HETATM   32  S   UNK     0    8680.0108674.357   0.000  0.00  0.00           S+0
HETATM   33  O   UNK     0    8680.7808675.693   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8679.2408675.693   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8681.3458673.588   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0    8674.6718675.897   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0    8669.3368674.357   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8670.6708672.047   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0    8672.0038672.818   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0    8669.2098666.935   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   13                                                            
CONECT    5   19                                                            
CONECT    6   17                                                            
CONECT    7   22                                                            
CONECT    8   20                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    4   19                                             
CONECT   14   13   15   12    3                                             
CONECT   15   14   16                                                       
CONECT   16   15   20   40                                                  
CONECT   17   18    6   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   13    5                                             
CONECT   20   19   16    8   22                                             
CONECT   21   22   38   17    1                                             
CONECT   22   21   23   20    7                                             
CONECT   23   22   24                                                       
CONECT   24   23   38                                                       
CONECT   25   26   37   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   28                                                            
CONECT   37   25                                                            
CONECT   38   39   25   21   24                                             
CONECT   39   38                                                            
CONECT   40   16                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

COMPND    HMDB0000036
HETATM    1  C1  UNL     1       2.194  -1.010  -2.782  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.776   0.418  -2.917  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.929   1.286  -3.288  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.089   1.414  -2.419  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.997   0.299  -2.181  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.123  -0.730  -2.878  1.00  0.00           O  
HETATM    7  N1  UNL     1       5.882   0.330  -1.020  1.00  0.00           N  
HETATM    8  C6  UNL     1       6.795  -0.743  -0.748  1.00  0.00           C  
HETATM    9  C7  UNL     1       7.594  -0.527   0.506  1.00  0.00           C  
HETATM   10  S1  UNL     1       6.511  -0.474   1.898  1.00  0.00           S  
HETATM   11  O2  UNL     1       7.311  -0.257   3.163  1.00  0.00           O  
HETATM   12  O3  UNL     1       5.498   0.610   1.758  1.00  0.00           O  
HETATM   13  O4  UNL     1       5.708  -1.954   1.955  1.00  0.00           O  
HETATM   14  C8  UNL     1       1.061   0.911  -1.694  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.657   2.361  -1.815  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.823   2.351  -1.539  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.876   1.268  -0.505  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.176   0.874  -0.013  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.012  -0.283   0.939  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.113  -1.356   0.461  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.159  -0.855  -0.170  1.00  0.00           C  
HETATM   22  O5  UNL     1       0.905  -0.224   0.823  1.00  0.00           O  
HETATM   23  C16 UNL     1      -0.160   0.157  -1.254  1.00  0.00           C  
HETATM   24  C17 UNL     1      -0.955  -0.497  -2.313  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.343  -0.840   1.384  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.594  -2.219   0.814  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.367  -0.950   2.873  1.00  0.00           C  
HETATM   28  C21 UNL     1      -4.669  -1.346   3.478  1.00  0.00           C  
HETATM   29  C22 UNL     1      -5.829  -0.518   2.972  1.00  0.00           C  
HETATM   30  O6  UNL     1      -5.982   0.688   3.654  1.00  0.00           O  
HETATM   31  C23 UNL     1      -5.804  -0.336   1.492  1.00  0.00           C  
HETATM   32  C24 UNL     1      -4.460   0.042   0.921  1.00  0.00           C  
HETATM   33  C25 UNL     1      -4.215   1.493   1.187  1.00  0.00           C  
HETATM   34  C26 UNL     1      -2.859   1.989   0.813  1.00  0.00           C  
HETATM   35  O7  UNL     1      -2.088   2.378   1.879  1.00  0.00           O  
HETATM   36  H1  UNL     1       1.253  -1.659  -2.834  1.00  0.00           H  
HETATM   37  H2  UNL     1       2.751  -1.377  -3.687  1.00  0.00           H  
HETATM   38  H3  UNL     1       2.758  -1.246  -1.894  1.00  0.00           H  
HETATM   39  H4  UNL     1       1.062   0.547  -3.802  1.00  0.00           H  
HETATM   40  H5  UNL     1       3.324   0.795  -4.257  1.00  0.00           H  
HETATM   41  H6  UNL     1       2.586   2.281  -3.722  1.00  0.00           H  
HETATM   42  H7  UNL     1       4.759   2.267  -2.793  1.00  0.00           H  
HETATM   43  H8  UNL     1       3.801   1.810  -1.397  1.00  0.00           H  
HETATM   44  H9  UNL     1       5.866   1.145  -0.383  1.00  0.00           H  
HETATM   45  H10 UNL     1       6.217  -1.693  -0.707  1.00  0.00           H  
HETATM   46  H11 UNL     1       7.504  -0.850  -1.614  1.00  0.00           H  
HETATM   47  H12 UNL     1       8.326  -1.374   0.626  1.00  0.00           H  
HETATM   48  H13 UNL     1       8.197   0.418   0.409  1.00  0.00           H  
HETATM   49  H14 UNL     1       5.949  -2.449   2.770  1.00  0.00           H  
HETATM   50  H15 UNL     1       1.802   0.780  -0.842  1.00  0.00           H  
HETATM   51  H16 UNL     1       1.133   2.906  -0.959  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.908   2.826  -2.783  1.00  0.00           H  
HETATM   53  H18 UNL     1      -1.170   3.331  -1.148  1.00  0.00           H  
HETATM   54  H19 UNL     1      -1.344   2.045  -2.458  1.00  0.00           H  
HETATM   55  H20 UNL     1      -0.180   1.600   0.322  1.00  0.00           H  
HETATM   56  H21 UNL     1      -2.903   0.705  -0.824  1.00  0.00           H  
HETATM   57  H22 UNL     1      -1.510   0.177   1.841  1.00  0.00           H  
HETATM   58  H23 UNL     1      -0.777  -1.933   1.382  1.00  0.00           H  
HETATM   59  H24 UNL     1      -1.598  -2.132  -0.174  1.00  0.00           H  
HETATM   60  H25 UNL     1       0.679  -1.722  -0.554  1.00  0.00           H  
HETATM   61  H26 UNL     1       0.486  -0.207   1.703  1.00  0.00           H  
HETATM   62  H27 UNL     1      -0.963  -1.616  -2.156  1.00  0.00           H  
HETATM   63  H28 UNL     1      -2.064  -0.271  -2.210  1.00  0.00           H  
HETATM   64  H29 UNL     1      -0.633  -0.337  -3.353  1.00  0.00           H  
HETATM   65  H30 UNL     1      -3.629  -2.212  -0.298  1.00  0.00           H  
HETATM   66  H31 UNL     1      -4.648  -2.481   1.129  1.00  0.00           H  
HETATM   67  H32 UNL     1      -2.937  -2.979   1.234  1.00  0.00           H  
HETATM   68  H33 UNL     1      -2.626  -1.753   3.159  1.00  0.00           H  
HETATM   69  H34 UNL     1      -2.994  -0.034   3.404  1.00  0.00           H  
HETATM   70  H35 UNL     1      -4.600  -1.139   4.574  1.00  0.00           H  
HETATM   71  H36 UNL     1      -4.884  -2.433   3.392  1.00  0.00           H  
HETATM   72  H37 UNL     1      -6.759  -1.110   3.215  1.00  0.00           H  
HETATM   73  H38 UNL     1      -6.860   1.047   3.386  1.00  0.00           H  
HETATM   74  H39 UNL     1      -6.507   0.511   1.257  1.00  0.00           H  
HETATM   75  H40 UNL     1      -6.246  -1.214   0.969  1.00  0.00           H  
HETATM   76  H41 UNL     1      -4.580  -0.142  -0.191  1.00  0.00           H  
HETATM   77  H42 UNL     1      -4.317   1.628   2.294  1.00  0.00           H  
HETATM   78  H43 UNL     1      -5.051   2.053   0.714  1.00  0.00           H  
HETATM   79  H44 UNL     1      -2.974   2.839   0.114  1.00  0.00           H  
HETATM   80  H45 UNL     1      -1.470   3.103   1.707  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   14   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6    6    7
CONECT    7    8   44
CONECT    8    9   45   46
CONECT    9   10   47   48
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   49
CONECT   14   15   23   50
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   23   55
CONECT   18   19   34   56
CONECT   19   20   25   57
CONECT   20   21   58   59
CONECT   21   22   23   60
CONECT   22   61
CONECT   23   24
CONECT   24   62   63   64
CONECT   25   26   27   32
CONECT   26   65   66   67
CONECT   27   28   68   69
CONECT   28   29   70   71
CONECT   29   30   31   72
CONECT   30   73
CONECT   31   32   74   75
CONECT   32   33   76
CONECT   33   34   77   78
CONECT   34   35   79
CONECT   35   80
END

HMDB0000036
     RDKit          3D
Taurocholic acid
 80 83  0  0  0  0  0  0  0  0999 V2000
    2.1937   -1.0101   -2.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764    0.4177   -2.9166 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9289    1.2855   -3.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    1.4137   -2.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973    0.2986   -2.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -0.7304   -2.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8819    0.3303   -1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7948   -0.7428   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941   -0.5273    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.4742    1.8985 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3108   -0.2567    3.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980    0.6100    1.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7077   -1.9540    1.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    0.9109   -1.6940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6575    2.3608   -1.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230    2.3505   -1.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    1.2677   -0.5047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1763    0.8741   -0.0131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0125   -0.2829    0.9394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1129   -1.3565    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.8552   -0.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9047   -0.2240    0.8229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1601    0.1566   -1.2539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9546   -0.4974   -2.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3427   -0.8398    1.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5943   -2.2185    0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670   -0.9500    2.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6694   -1.3464    3.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8286   -0.5181    2.9724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9823    0.6877    3.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043   -0.3360    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4597    0.0418    0.9210 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2149    1.4932    1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    1.9889    0.8133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0884    2.3776    1.8789 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -1.6592   -2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.3768   -3.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581   -1.2457   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.5469   -3.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    0.7955   -4.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    2.2805   -3.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592    2.2666   -2.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8013    1.8101   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657    1.1451   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172   -1.6927   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -0.8500   -1.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3265   -1.3744    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1968    0.4183    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9488   -2.4491    2.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022    0.7802   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327    2.9056   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077    2.8262   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702    3.3311   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440    2.0450   -2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    1.5996    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    0.7049   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    0.1765    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7772   -1.9331    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -2.1316   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -1.7216   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.2072    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632   -1.6163   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641   -0.2705   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6330   -0.3375   -3.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -2.2122   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479   -2.4815    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -2.9794    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263   -1.7528    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -0.0339    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6004   -1.1387    4.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840   -2.4326    3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7594   -1.1102    3.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8602    1.0469    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    0.5111    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2459   -1.2137    0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -0.1425   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    1.6280    2.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0505    2.0530    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737    2.8391    0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    3.1028    1.7073 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  6
 19 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 23 14  1  0
 32 25  1  0
 23 17  1  0
 34 18  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 13 49  1  0
 14 50  1  1
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  6
 19 57  1  1
 20 58  1  0
 20 59  1  0
 21 60  1  6
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 24 62  1  0
 24 63  1  0
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 27 68  1  0
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 28 70  1  0
 28 71  1  0
 29 72  1  6
 30 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  6
 33 77  1  0
 33 78  1  0
 34 79  1  6
 35 80  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurine	ChEBI
Cholic acid taurine conjugate	ChEBI
Choloyl-taurine	ChEBI
Cholyltaurine	ChEBI
N-Choloyltaurine	ChEBI
Taurocholate	ChEBI
3a,7a,12a-Trihydroxy-5b-cholanate 24-taurine	Generator
3a,7a,12a-Trihydroxy-5b-cholanic acid 24-taurine	Generator
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate 24-taurine	Generator
3Α,7α,12α-trihydroxy-5β-cholanate 24-taurine	Generator
3Α,7α,12α-trihydroxy-5β-cholanic acid 24-taurine	Generator
Cholate taurine conjugate	Generator
Cholic acid taurine conjugic acid	Generator
Cholaic acid	HMDB
Cholaate	HMDB
Taurine cholate	HMDB
Taurocholic acid, (7 beta)-isomer	HMDB
Taurocholic acid, (5 alpha)-isomer	HMDB

Chemical Formula

C₂₆H₄₅NO₇S

Average Mass

515.7030 Da

Monoisotopic Mass

515.29167 Da

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

Traditional Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

CAS Registry Number

81-24-3

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

InChI Key

WBWWGRHZICKQGZ-HZAMXZRMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Polygala amarella	KNApSAcK Database	22123792
Polygala tenuifolia Willd.	KNApSAcK Database	22123792
Selenarctos thibetanus	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Secondary alcohol
Carboximidic acid
Polyol
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

amino sulfonic acid (CHEBI:28865 )
bile acid taurine conjugate (CHEBI:28865 )
Taurine conjugates (LMST05040001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	125 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	555.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.247 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.077 g/L	ALOGPS
logP	0.79	ALOGPS
logP	-0.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	-0.88	ChemAxon
pKa (Strongest Basic)	-0.053	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.16 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.19 m³·mol⁻¹	ChemAxon
Polarizability	57.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000036

DrugBank ID

DB04348

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28865

Good Scents ID

rw1611841

References

General References

van Montfoort JE, Muller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ: Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5. [PubMed:11408531 ]
Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481 ]
Hoekman MF, Rientjes JM, Twisk J, Planta RJ, Princen HM, Mager WH: Transcriptional regulation of the gene encoding cholesterol 7 alpha-hydroxylase in the rat. Gene. 1993 Aug 25;130(2):217-23. [PubMed:8359688 ]
Sandker GW, Weert B, Olinga P, Wolters H, Slooff MJ, Meijer DK, Groothuis GM: Characterization of transport in isolated human hepatocytes. A study with the bile acid taurocholic acid, the uncharged ouabain and the organic cations vecuronium and rocuronium. Biochem Pharmacol. 1994 Jun 15;47(12):2193-200. [PubMed:7913319 ]
Kullak-Ublick GA, Glasa J, Boker C, Oswald M, Grutzner U, Hagenbuch B, Stieger B, Meier PJ, Beuers U, Kramer W, Wess G, Paumgartner G: Chlorambucil-taurocholate is transported by bile acid carriers expressed in human hepatocellular carcinomas. Gastroenterology. 1997 Oct;113(4):1295-305. [PubMed:9322525 ]
Claudel T, Inoue Y, Barbier O, Duran-Sandoval D, Kosykh V, Fruchart J, Fruchart JC, Gonzalez FJ, Staels B: Farnesoid X receptor agonists suppress hepatic apolipoprotein CIII expression. Gastroenterology. 2003 Aug;125(2):544-55. [PubMed:12891557 ]
Rizzo G, Renga B, Mencarelli A, Pellicciari R, Fiorucci S: Role of FXR in regulating bile acid homeostasis and relevance for human diseases. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Sep;5(3):289-303. [PubMed:16178789 ]
Duan RD, Cheng Y, Tauschel HD, Nilsson A: Effects of ursodeoxycholate and other bile salts on levels of rat intestinal alkaline sphingomyelinase: a potential implication in tumorigenesis. Dig Dis Sci. 1998 Jan;43(1):26-32. [PubMed:9508530 ]
Akao T: Influence of various bile acids on the metabolism of glycyrrhizin and glycyrrhetic acid by Ruminococcus sp. PO1-3 of human intestinal bacteria. Biol Pharm Bull. 1999 Aug;22(8):787-93. [PubMed:10480314 ]
Jigorel E, Le Vee M, Boursier-Neyret C, Bertrand M, Fardel O: Functional expression of sinusoidal drug transporters in primary human and rat hepatocytes. Drug Metab Dispos. 2005 Oct;33(10):1418-22. Epub 2005 Jul 13. [PubMed:16014767 ]
Zahner D, Eckhardt U, Petzinger E: Transport of taurocholate by mutants of negatively charged amino acids, cysteines, and threonines of the rat liver sodium-dependent taurocholate cotransporting polypeptide Ntcp. Eur J Biochem. 2003 Mar;270(6):1117-27. [PubMed:12631271 ]
Wang LF, Luo H, Miyoshi M, Imoto T, Hiji Y, Sasaki T: Inhibitory effect of gymnemic acid on intestinal absorption of oleic acid in rats. Can J Physiol Pharmacol. 1998 Oct-Nov;76(10-11):1017-23. [PubMed:10100884 ]
Yamamoto Y, Moore R, Hess HA, Guo GL, Gonzalez FJ, Korach KS, Maronpot RR, Negishi M: Estrogen receptor alpha mediates 17alpha-ethynylestradiol causing hepatotoxicity. J Biol Chem. 2006 Jun 16;281(24):16625-31. Epub 2006 Apr 10. [PubMed:16606610 ]
Kwekkeboom J, Princen HM, van Voorthuizen EM, Meijer P, Kempen HJ: Comparison of taurocholate accumulation in cultured hepatocytes of pig, rat and man. Biochem Biophys Res Commun. 1989 Jul 31;162(2):619-25. [PubMed:2757635 ]
Claudel T, Sturm E, Duez H, Torra IP, Sirvent A, Kosykh V, Fruchart JC, Dallongeville J, Hum DW, Kuipers F, Staels B: Bile acid-activated nuclear receptor FXR suppresses apolipoprotein A-I transcription via a negative FXR response element. J Clin Invest. 2002 Apr;109(7):961-71. [PubMed:11927623 ]
Johnson RC, Shah SN: Cholesterol ester hydrolase(s) in mammalian brain: is there a myelin-specific cholesterol ester hydrolase? Neurochem Res. 1986 Nov;11(11):1571-82. [PubMed:3683732 ]
Balakrishnan A, Sussman DJ, Polli JE: Development of stably transfected monolayer overexpressing the human apical sodium-dependent bile acid transporter (hASBT). Pharm Res. 2005 Aug;22(8):1269-80. Epub 2005 Aug 3. [PubMed:16078136 ]
Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
Williamson C, Gorelik J, Eaton BM, Lab M, de Swiet M, Korchev Y: The bile acid taurocholate impairs rat cardiomyocyte function: a proposed mechanism for intra-uterine fetal death in obstetric cholestasis. Clin Sci (Lond). 2001 Apr;100(4):363-9. [PubMed:11256973 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Taurocholic acid (NP0000461)

MOL for NP0000461 (Taurocholic acid)

3D MOL for NP0000461 (Taurocholic acid)

3D SDF for NP0000461 (Taurocholic acid)

3D-SDF for NP0000461 (Taurocholic acid)

PDB for NP0000461 (Taurocholic acid)

3D PDB for NP0000461 (Taurocholic acid)

SMILES for NP0000461 (Taurocholic acid)

INCHI for NP0000461 (Taurocholic acid)

Structure for NP0000461 (Taurocholic acid)

3D Structure for NP0000461 (Taurocholic acid)