NP-MRD: Showing NP-Card for Lithocholic acid (NP0000813)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:30 UTC

NP-MRD ID

NP0000813

Secondary Accession Numbers

None

Natural Product 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
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 18 19  1  0  0  0  0
 10  3  1  6  0  0  0
  8 12  1  0  0  0  0
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 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
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 25 31  1  6  0  0  0
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 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
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   -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
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 20 21  1  0
 21 22  1  1
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 23 24  1  0
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 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
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 25 64  1  0
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 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
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 12 13  1  0  0  0  0
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 10  3  1  6  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
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 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
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 24 25  1  0  0  0  0
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 25 31  1  6  0  0  0
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 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>
NP0000813

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

376.5726 Da

Monoisotopic Mass

376.29775 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, 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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 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	¹H NMR Spectrum (1D, 300 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	¹H NMR Spectrum (1D, 400 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	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 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	¹H NMR Spectrum (1D, 700 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	¹H NMR Spectrum (1D, 800 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	¹H NMR Spectrum (1D, 900 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
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Bos taurus domesticus	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000761

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1255741

References

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 ]
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Showing NP-Card for Lithocholic acid (NP0000813)

MOL for NP0000813 (Lithocholic acid)

3D MOL for NP0000813 (Lithocholic acid)

3D SDF for NP0000813 (Lithocholic acid)

3D-SDF for NP0000813 (Lithocholic acid)

PDB for NP0000813 (Lithocholic acid)

3D PDB for NP0000813 (Lithocholic acid)

SMILES for NP0000813 (Lithocholic acid)

INCHI for NP0000813 (Lithocholic acid)

Structure for NP0000813 (Lithocholic acid)

3D Structure for NP0000813 (Lithocholic acid)