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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (8) Show 13 proteins XML

enzymes (5)transporters (8) Show 13 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:06 UTC

HMDB ID

HMDB0000761

Secondary Accession Numbers

HMDB00761

Metabolite Identification

Common Name

Lithocholic acid

Description

Lithocholic acid, also known as 3alpha-hydroxy-5beta-cholan-24-oic acid or LCA, is a secondary bile acid. It is formed from chenodeoxycholate by bacterial action and is usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute and depends 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 ). When present in sufficiently high levels, lithocholic acid can act as an oncometabolite. An oncometabolite is a compound that when present at chronically high levels promotes tumour growth and survival. Chronically high levels of lithocholic acid are associated with several forms of cancer including colon cancer, pancreatic cancer, esophageal cancer, and many other GI cancers. High bile acid levels lead to the generation of reactive oxygen species and reactive nitrogen species, disruption of the cell membrane and mitochondria, induction of DNA damage, mutation and apoptosis, and the development of reduced apoptosis capability upon chronic exposure (PMID: 24884764 ). Dietary fibre can bind to lithocholic acid and aid in its excretion in stool. As such, fibre can protect against colon cancer.

Structure

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


  Mrv1652305271900192D          

 32 35  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.086310000.4738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.421910001.2275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.243510001.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.727610000.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549210000.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.033210000.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.884810001.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.937710001.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.905610000.5712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  3  1  6  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13  4  1  1  0  0  0
 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
 15 19  1  0  0  0  0
 18  5  1  6  0  0  0
 19  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 31  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 30  2  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 32  1  6  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21  7  1  6  0  0  0
 20  1  1  1  0  0  0
M  END

HMDB0000761
     RDKit          3D
Lithocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
   -4.5845    1.1135   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    0.1639   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4475   -0.3487    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.1291    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7699   -0.4645   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0685   -0.7898   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5646    0.5438   -0.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    0.7612   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3905    2.1088    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911    2.2981    0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556    1.0612   -0.0978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0653    0.6768    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0156    1.8183    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.3679   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987    0.0672    0.6912 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0585   -0.2539    0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381   -0.4885   -0.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0186    0.7594   -0.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371   -1.4232   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -1.2924   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -0.9925   -0.0846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9141   -2.2723    0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -0.5774   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4718   -1.6412   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -1.2366   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769    0.0367    0.1788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5392   -0.0154    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    1.9102   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    0.6748   -2.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2912    1.7285   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -0.7262   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725    0.4329    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.0953    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610   -2.0104   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5838    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    1.3948   -0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    0.9552   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    2.9138   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593    2.1607    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    3.1411   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.5324    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2018    1.1281   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.4237    1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494    2.4044   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953    2.5083    0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    1.2543   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    2.1650    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664    0.2292    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247    0.6665    1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.0493    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7469   -0.9377   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4477    1.2897   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111   -2.4805   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4259   -1.2236   -2.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -0.5554   -2.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -2.2706   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.4979    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -3.1214    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -2.1332    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -0.3134   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566   -1.8788    1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963   -2.6068   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -1.0515   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -2.0757   -0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.0798    2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    0.4289    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    0.4978    2.0703 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  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  6
 12 43  1  1
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
M  END


  Mrv1652305271900192D          

 32 35  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.086310000.4738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.421910001.2275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.243510001.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.727610000.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.549210000.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.033210000.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.884810001.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.937710001.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.905610000.5712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  3  1  6  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13  4  1  1  0  0  0
 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
 15 19  1  0  0  0  0
 18  5  1  6  0  0  0
 19  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 31  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 30  2  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 32  1  6  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21  7  1  6  0  0  0
 20  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000761

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

> <INCHI_KEY>
SMEROWZSTRWXGI-HVATVPOCSA-N

> <FORMULA>
C24H40O3

> <MOLECULAR_WEIGHT>
376.5726

> <EXACT_MASS>
376.297745146

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
45.80324899910681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
5.022070320666666

> <ALOGPS_LOGS>
-5.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396321121705

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.791043111632056

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569565580180343

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
107.68129999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.05e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000761
     RDKit          3D
Lithocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
   -4.5845    1.1135   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    0.1639   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4475   -0.3487    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.1291    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7699   -0.4645   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0685   -0.7898   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5646    0.5438   -0.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    0.7612   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3905    2.1088    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911    2.2981    0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556    1.0612   -0.0978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0653    0.6768    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0156    1.8183    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.3679   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987    0.0672    0.6912 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0585   -0.2539    0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381   -0.4885   -0.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0186    0.7594   -0.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371   -1.4232   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -1.2924   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -0.9925   -0.0846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9141   -2.2723    0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -0.5774   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4718   -1.6412   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -1.2366   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769    0.0367    0.1788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5392   -0.0154    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    1.9102   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    0.6748   -2.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2912    1.7285   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -0.7262   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725    0.4329    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.0953    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610   -2.0104   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5838    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    1.3948   -0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    0.9552   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    2.9138   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593    2.1607    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    3.1411   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.5324    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2018    1.1281   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.4237    1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494    2.4044   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953    2.5083    0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    1.2543   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    2.1650    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664    0.2292    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247    0.6665    1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.0493    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7469   -0.9377   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4477    1.2897   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111   -2.4805   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4259   -1.2236   -2.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -0.5554   -2.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -2.2706   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.4979    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -3.1214    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -2.1332    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -0.3134   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566   -1.8788    1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963   -2.6068   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -1.0515   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -2.0757   -0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.0798    2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    0.4289    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    0.4978    2.0703 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  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  6
 12 43  1  1
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.6948667.551   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.3218668.958   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.8558669.118   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.7588667.873   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8673.2928668.033   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8674.1958666.788   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0    8673.9188669.440   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8668.4178670.203   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0    8670.2248667.733   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   12                                                            
CONECT    3   10                                                            
CONECT    4   13                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7   21                                                            
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    3                                                  
CONECT   11   10   13                                                       
CONECT   12   13    8    2   18                                             
CONECT   13   12   14   11    4                                             
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   17   20                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12    5                                             
CONECT   19   18   15    6   21                                             
CONECT   20   21   24   16    1                                             
CONECT   21   20   22   19    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   20   23   32                                             
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000761
HETATM    1  C1  UNL     1      -4.584   1.114  -1.588  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.759   0.164  -0.754  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.447  -0.349   0.427  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.686  -1.129   0.114  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.770  -0.464  -0.572  1.00  0.00           C  
HETATM    6  O1  UNL     1      -7.068  -0.790  -1.770  1.00  0.00           O  
HETATM    7  O2  UNL     1      -7.565   0.544  -0.040  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.427   0.761  -0.572  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.390   2.109   0.121  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.891   2.298   0.418  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.256   1.061  -0.098  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.065   0.677   0.393  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.016   1.818   0.109  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.452   1.368  -0.065  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.599   0.067   0.691  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.059  -0.254   0.893  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.738  -0.489  -0.409  1.00  0.00           C  
HETATM   18  O3  UNL     1       6.019   0.759  -0.971  1.00  0.00           O  
HETATM   19  C16 UNL     1       5.037  -1.423  -1.326  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.555  -1.292  -1.379  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.881  -0.992  -0.085  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.914  -2.272   0.758  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.472  -0.577  -0.383  1.00  0.00           C  
HETATM   24  C21 UNL     1       0.472  -1.641  -0.031  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.913  -1.237  -0.461  1.00  0.00           C  
HETATM   26  C23 UNL     1      -1.377   0.037   0.179  1.00  0.00           C  
HETATM   27  C24 UNL     1      -1.539  -0.015   1.653  1.00  0.00           C  
HETATM   28  H1  UNL     1      -3.877   1.910  -2.003  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.016   0.675  -2.499  1.00  0.00           H  
HETATM   30  H3  UNL     1      -5.291   1.728  -0.976  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.600  -0.726  -1.449  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.773   0.433   1.158  1.00  0.00           H  
HETATM   33  H6  UNL     1      -3.773  -1.095   0.943  1.00  0.00           H  
HETATM   34  H7  UNL     1      -5.361  -2.010  -0.513  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.114  -1.584   1.058  1.00  0.00           H  
HETATM   36  H9  UNL     1      -7.655   1.395  -0.612  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.016   0.955  -1.611  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.777   2.914  -0.538  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.959   2.161   1.046  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.560   3.141  -0.244  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.704   2.532   1.463  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.202   1.128  -1.220  1.00  0.00           H  
HETATM   43  H16 UNL     1       1.172   0.424   1.454  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.649   2.404  -0.768  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.995   2.508   0.976  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.715   1.254  -1.145  1.00  0.00           H  
HETATM   47  H20 UNL     1       4.129   2.165   0.323  1.00  0.00           H  
HETATM   48  H21 UNL     1       3.166   0.229   1.686  1.00  0.00           H  
HETATM   49  H22 UNL     1       5.525   0.667   1.354  1.00  0.00           H  
HETATM   50  H23 UNL     1       5.218  -1.049   1.639  1.00  0.00           H  
HETATM   51  H24 UNL     1       6.747  -0.938  -0.168  1.00  0.00           H  
HETATM   52  H25 UNL     1       6.448   1.290  -0.226  1.00  0.00           H  
HETATM   53  H26 UNL     1       5.311  -2.481  -1.111  1.00  0.00           H  
HETATM   54  H27 UNL     1       5.426  -1.224  -2.367  1.00  0.00           H  
HETATM   55  H28 UNL     1       3.250  -0.555  -2.167  1.00  0.00           H  
HETATM   56  H29 UNL     1       3.152  -2.271  -1.742  1.00  0.00           H  
HETATM   57  H30 UNL     1       3.984  -2.498   0.924  1.00  0.00           H  
HETATM   58  H31 UNL     1       2.519  -3.121   0.156  1.00  0.00           H  
HETATM   59  H32 UNL     1       2.353  -2.133   1.713  1.00  0.00           H  
HETATM   60  H33 UNL     1       1.307  -0.313  -1.462  1.00  0.00           H  
HETATM   61  H34 UNL     1       0.457  -1.879   1.047  1.00  0.00           H  
HETATM   62  H35 UNL     1       0.696  -2.607  -0.578  1.00  0.00           H  
HETATM   63  H36 UNL     1      -0.876  -1.052  -1.552  1.00  0.00           H  
HETATM   64  H37 UNL     1      -1.593  -2.076  -0.234  1.00  0.00           H  
HETATM   65  H38 UNL     1      -1.570  -1.080   2.004  1.00  0.00           H  
HETATM   66  H39 UNL     1      -0.683   0.429   2.238  1.00  0.00           H  
HETATM   67  H40 UNL     1      -2.425   0.498   2.070  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    8   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6    6    7
CONECT    7   36
CONECT    8    9   26   37
CONECT    9   10   38   39
CONECT   10   11   40   41
CONECT   11   12   26   42
CONECT   12   13   23   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   21   48
CONECT   16   17   49   50
CONECT   17   18   19   51
CONECT   18   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   23
CONECT   22   57   58   59
CONECT   23   24   60
CONECT   24   25   61   62
CONECT   25   26   63   64
CONECT   26   27
CONECT   27   65   66   67
END

HMDB0000761
     RDKit          3D
Lithocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
   -4.5845    1.1135   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    0.1639   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4475   -0.3487    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.1291    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7699   -0.4645   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0685   -0.7898   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5646    0.5438   -0.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    0.7612   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3905    2.1088    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911    2.2981    0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556    1.0612   -0.0978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0653    0.6768    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0156    1.8183    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.3679   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987    0.0672    0.6912 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0585   -0.2539    0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381   -0.4885   -0.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0186    0.7594   -0.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371   -1.4232   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -1.2924   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -0.9925   -0.0846 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9141   -2.2723    0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -0.5774   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4718   -1.6412   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -1.2366   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769    0.0367    0.1788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5392   -0.0154    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    1.9102   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    0.6748   -2.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2912    1.7285   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -0.7262   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725    0.4329    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.0953    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610   -2.0104   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1136   -1.5838    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    1.3948   -0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    0.9552   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775    2.9138   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593    2.1607    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    3.1411   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.5324    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2018    1.1281   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.4237    1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494    2.4044   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953    2.5083    0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    1.2543   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    2.1650    0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664    0.2292    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247    0.6665    1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.0493    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7469   -0.9377   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4477    1.2897   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111   -2.4805   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4259   -1.2236   -2.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -0.5554   -2.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -2.2706   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.4979    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -3.1214    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -2.1332    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -0.3134   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566   -1.8788    1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963   -2.6068   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -1.0515   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -2.0757   -0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.0798    2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    0.4289    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    0.4978    2.0703 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  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  6
 12 43  1  1
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta)-3-Hydroxycholan-24-Oic acid	ChEBI
3alpha-Hydroxy-5beta-cholanate	ChEBI
3alpha-Hydroxy-5beta-cholanic acid	ChEBI
3alpha-Hydroxy-5beta-cholanoic acid	ChEBI
5beta-Cholanic acid-3alpha-ol	ChEBI
Lithocholate	Kegg
(3a,5b)-3-Hydroxycholan-24-Oate	Generator
(3a,5b)-3-Hydroxycholan-24-Oic acid	Generator
(3alpha,5beta)-3-Hydroxycholan-24-Oate	Generator
(3Α,5β)-3-hydroxycholan-24-Oate	Generator
(3Α,5β)-3-hydroxycholan-24-Oic acid	Generator
3a-Hydroxy-5b-cholanate	Generator
3a-Hydroxy-5b-cholanic acid	Generator
3Α-hydroxy-5β-cholanate	Generator
3Α-hydroxy-5β-cholanic acid	Generator
3a-Hydroxy-5b-cholanoate	Generator
3a-Hydroxy-5b-cholanoic acid	Generator
3alpha-Hydroxy-5beta-cholanoate	Generator
3Α-hydroxy-5β-cholanoate	Generator
3Α-hydroxy-5β-cholanoic acid	Generator
5b-Cholanate-3a-ol	Generator
5b-Cholanic acid-3a-ol	Generator
5beta-Cholanate-3alpha-ol	Generator
5Β-cholanate-3α-ol	Generator
5Β-cholanic acid-3α-ol	Generator
Acid, lithocholic	HMDB

Chemical Formula

C₂₄H₄₀O₃

Average Molecular Weight

376.5726

Monoisotopic Molecular Weight

376.297745146

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

434-13-9

SMILES

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

InChI Identifier

InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

InChI Key

SMEROWZSTRWXGI-HVATVPOCSA-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
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:16325 )
monohydroxy-5beta-cholanic acid (CHEBI:16325 )
C24 bile acids, alcohols, and derivatives (C03990 )
Cholane and derivatives (C03990 )
C24 bile acids, alcohols, and derivatives (LMST04010003 )

Ontology

Not Available

Intestine (HMDB: HMDB0000761)
Liver (HMDB: HMDB0000761)

Biofluid or Excreta

Non-excretory biofluid

Bile (PMID: 16548228)
Blood (PMID: 15185309)

Excreta

Urine (PMID: 2621422)
Feces (PMID: 22664055)

Cellular substructure

Extracellular (HMDB: HMDB0000761)

Intestine (HMDB: HMDB0000761)
Liver (HMDB: HMDB0000761)

Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0000761)

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0000314)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0000318)
Familial Hypercholanemia (FHCA) (PathBank: SMP0000317)
Zellweger Syndrome (PathBank: SMP0000316)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0000315)
27-Hydroxylase Deficiency (PathBank: SMP0000720)

Role

Industrial application

Pharmaceutical industry

Biomarker

Cystic fibrosis (MarkerDB: MDB00000245)
Cirrhosis (MarkerDB: MDB00000245)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	186 °C	Not Available
Boiling Point	511.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.00038 mg/mL	Not Available
LogP	6.700 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	200.333	30932474
[M-H]-	MetCCS_train_neg	199.948	30932474
[M-H]-	Not Available	201.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001232
[M+H]+	Not Available	210.779	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001232

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0005 g/L	ALOGPS
logP	4.38	ALOGPS
logP	5.02	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.68 m³·mol⁻¹	ChemAxon
Polarizability	45.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	198.428	32859911
AllCCS	[M-H]-	197.296	32859911
DeepCCS	[M-2H]-	228.295	30932474
DeepCCS	[M+Na]+	202.613	30932474
AllCCS	[M+H]+	198.4	32859911
AllCCS	[M+H-H2O]+	196.2	32859911
AllCCS	[M+NH4]+	200.5	32859911
AllCCS	[M+Na]+	201.0	32859911
AllCCS	[M-H]-	197.3	32859911
AllCCS	[M+Na-2H]-	198.5	32859911
AllCCS	[M+HCOO]-	200.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lithocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3522.5	Standard polar	33892256
Lithocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3167.6	Standard non polar	33892256
Lithocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3255.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lithocholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3264.1	Semi standard non polar	33892256
Lithocholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3169.0	Semi standard non polar	33892256
Lithocholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3182.4	Semi standard non polar	33892256
Lithocholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3492.6	Semi standard non polar	33892256
Lithocholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3446.1	Semi standard non polar	33892256
Lithocholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3714.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Lithocholic acid GC-MS (2 TMS)	splash10-05rv-4920000000-de3b80b61b7f2c19a68f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lithocholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0009000000-e3a2f64bd8834594c115	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-b27641d2926e1d3e69ed	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-0900000000-d895d3aa84e2458a8507	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid 30V, Negative-QTOF	splash10-004i-0009000000-2ba1032289e0943a67f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid 45V, Negative-QTOF	splash10-004i-0009000000-86747220d494c9f61e75	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lithocholic acid 60V, Negative-QTOF	splash10-004i-0009000000-77da6177e733cee0351f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 10V, Positive-QTOF	splash10-0a4i-0009000000-5c13680398c0dc8c4c9a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 20V, Positive-QTOF	splash10-0bu3-0029000000-43d4d1cfa50f2747cbc1	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 40V, Positive-QTOF	splash10-01ot-1196000000-84d5d023f420f6586e2d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 10V, Negative-QTOF	splash10-004i-0009000000-f317b23fea7a9c31f96a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 20V, Negative-QTOF	splash10-0a6r-0009000000-7369aef23afe9f4d2fd4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-c710ff23af9538d7b6ed	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 10V, Negative-QTOF	splash10-004i-0009000000-eccc9e9b8c78169f5313	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 20V, Negative-QTOF	splash10-056r-0009000000-baf4e51649a0429955f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 40V, Negative-QTOF	splash10-05fr-1019000000-03efb470f50587874e8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 10V, Positive-QTOF	splash10-004i-0019000000-680bfb6696f335494117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 20V, Positive-QTOF	splash10-0a4r-4097000000-cc3f365c530405dbd341	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lithocholic acid 40V, Positive-QTOF	splash10-0a4m-9730000000-3ac8b523250e6ccd1a4f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Urine

Tissue Locations

Intestine
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bile	Detected and Quantified	930 (890-960) uM	Adult (>18 years old)	Both	Normal	16548228	details
Blood	Detected and Quantified	0.08 +/- 0.02 uM	Newborn (0-30 days old)	Both	Normal	16553252	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.33 +/-0.04 uM	Adult (>18 years old)	Both	Normal	15185309	details
Feces	Detected and Quantified	1016.60 +/- 647.31 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.16 (0.10-0.20) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.5 (0.5-3.0) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	0.11 +/- 0.04 uM	Newborn (0-30 days old)	Both	Extrahepatic biliary atresia (EHBA)	16553252	details
Blood	Detected and Quantified	0.11 +/- 0.02 uM	Adult (>18 years old)	Both	Cystic fibrosis	15185309	details
Blood	Detected and Quantified	0.16 +/- 0.07 uM	Children (1-13 years old)	Both	Cystic fibrosis	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	24284963	details
Urine	Detected and Quantified	0.32 (0.10-0.52) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.1 (0.41-2.4) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Biliary atresia
Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [PubMed:16553252 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Primary biliary cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]

Associated OMIM IDs

219700 (Cystic fibrosis)
210500 (Biliary atresia)
114500 (Colorectal cancer)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Lithocholic_acid

METLIN ID

209

PubChem Compound

9903

PDB ID

Not Available

ChEBI ID

16325

Food Biomarker Ontology

Not Available

VMH ID

HC02191

MarkerDB ID

MDB00000245

Good Scents ID

rw1255741

References

Synthesis Reference

Xu, Zhengbang; Li, Kaixi; Zhao, Huaming. Synthesis of lithocholic acid by Huang-Min-Lon modification in the presence of crown ether. Sichuan Daxue Xuebao, Ziran Kexueban (1992), 29(4), 527-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. [PubMed:11344576 ]
Deleze G, Paumgartner G, Karlaganis G, Giger W, Reinhard M, Sidiropoulos D: Bile acid pattern in human amniotic fluid. Eur J Clin Invest. 1978 Feb;8(1):41-5. [PubMed:417931 ]
Beher WT, Gabbard A, Norum RA, Stradnieks S: Effect of blood high density lipoprotein cholesterol concentration on fecal steroid excretion in humans. Life Sci. 1983 Jun 27;32(26):2933-7. [PubMed:6865641 ]
Rudi J, Schonig T, Stremmel W: -Therapy with ursodeoxycholic acid in primary biliary cirrhosis in pregnancy-. Z Gastroenterol. 1996 Mar;34(3):188-91. [PubMed:8650973 ]
Stadler J, Yeung KS, Furrer R, Marcon N, Himal HS, Bruce WR: Proliferative activity of rectal mucosa and soluble fecal bile acids in patients with normal colons and in patients with colonic polyps or cancer. Cancer Lett. 1988 Jan;38(3):315-20. [PubMed:3349450 ]
Greco AV, Mingrone G: Serum bile acid concentrations in mild liver cirrhosis. Clin Chim Acta. 1993 Nov 30;221(1-2):183-9. [PubMed:8149635 ]
Kitahara M, Sakata S, Sakamoto M, Benno Y: Comparison among fecal secondary bile acid levels, fecal microbiota and Clostridium scindens cell numbers in Japanese. Microbiol Immunol. 2004;48(5):367-75. [PubMed:15215624 ]
Dew MJ, van Berge Henegouwen GP, Huybregts AW, Allan RN: Hepatotoxic effect of bile acids in inflammatory bowel disease. Gastroenterology. 1980 Jun;78(6):1393-401. [PubMed:7372059 ]
Ceryak S, Bouscarel B, Fromm H: Comparative binding of bile acids to serum lipoproteins and albumin. J Lipid Res. 1993 Oct;34(10):1661-74. [PubMed:8245717 ]
Eklund A, Norlander A, Norman A: Bile acid synthesis and excretion following release of total extrahepatic cholestasis by percutaneous transhepatic drainage. Eur J Clin Invest. 1980 Oct;10(5):349-55. [PubMed:6777167 ]
Balistreri WF, Suchy FJ, Farrell MK, Heubi JE: Pathologic versus physiologic cholestasis: elevated serum concentration of a secondary bile acid in the presence of hepatobiliary disease. J Pediatr. 1981 Mar;98(3):399-402. [PubMed:7205448 ]
Fouin-Fortunet H, Le Quernec L, Erlinger S, Lerebours E, Colin R: Hepatic alterations during total parenteral nutrition in patients with inflammatory bowel disease: a possible consequence of lithocholate toxicity. Gastroenterology. 1982 May;82(5 Pt 1):932-7. [PubMed:6800873 ]
Hofmann AF: [Enterohepatic circulation of bile acids and biliary lipid secretion]. Minerva Med. 1977 Sep 19;68(43):3011-7. [PubMed:409965 ]
Loof L, Wengle B: Enzymatic sulphation of bile salts in human liver. Biochim Biophys Acta. 1978 Sep 28;530(3):451-60. [PubMed:698243 ]
Tinker LF, Schneeman BO, Davis PA, Gallaher DD, Waggoner CR: Consumption of prunes as a source of dietary fiber in men with mild hypercholesterolemia. Am J Clin Nutr. 1991 May;53(5):1259-65. [PubMed:1850578 ]
Farrell GC, Duddy SK, Kass GE, Llopis J, Gahm A, Orrenius S: Release of Ca2+ from the endoplasmic reticulum is not the mechanism for bile acid-induced cholestasis and hepatotoxicity in the intact rat liver. J Clin Invest. 1990 Apr;85(4):1255-9. [PubMed:2318979 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Ajouz H, Mukherji D, Shamseddine A: Secondary bile acids: an underrecognized cause of colon cancer. World J Surg Oncol. 2014 May 24;12:164. doi: 10.1186/1477-7819-12-164. [PubMed:24884764 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Enzyme Details

2. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Reactions

Lithocholic acid + NADPH + Oxygen → Hyodeoxycholic acid + NADP + Water	details

Enzyme Details

4. Bile acid receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus
Gene Name:: NR1H4
Uniprot ID:: Q96RI1
Molecular weight:: 55913.9

Enzyme Details

5. 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

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Lithocholic acid (HMDB0000761)

MOL for HMDB0000761 (Lithocholic acid)

3D MOL for HMDB0000761 (Lithocholic acid)

3D SDF for HMDB0000761 (Lithocholic acid)

3D-SDF for HMDB0000761 (Lithocholic acid)

PDB for HMDB0000761 (Lithocholic acid)

3D PDB for HMDB0000761 (Lithocholic acid)

SMILES for HMDB0000761 (Lithocholic acid)

INCHI for HMDB0000761 (Lithocholic acid)

Structure for HMDB0000761 (Lithocholic acid)

3D Structure for HMDB0000761 (Lithocholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

Transporters

References

References