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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (8) Show 10 proteins XML

enzymes (2)transporters (8) Show 10 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:04 UTC

HMDB ID

HMDB0000626

Secondary Accession Numbers

HMDB00626

Metabolite Identification

Common Name

Deoxycholic acid

Description

Deoxycholic acid is a secondary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. 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, deoxycholic acid can act as a hepatotoxin, a metabotoxin, and an oncometabolite. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. An oncometabolite is a compound, when present at chronically high levels, that promotes tumour growth and survival. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. 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 ). Chronically high levels of deoxycholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including deoxycholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia. Chronically high levels of deoxycholic acid are also associated with several forms of cancer including colon cancer, pancreatic cancer, esophageal cancer, and many other GI cancers.

Structure

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

            
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0345    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
 9998.2016 9999.7849    0.0000 C   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
 9999.627010001.2705    0.0000 O   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
 9999.6270 9999.7849    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  1  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
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  1  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
10001.126610001.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.412110001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.841010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555410001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.861710000.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.984510001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 27  1  6  0  0  0
 11  2  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  3  1  1  0  0  0
 13  4  1  1  0  0  0
 17  6  1  6  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  5  1  6  0  0  0
 20  8  1  1  0  0  0
 21 31  1  6  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22  1  1  1  0  0  0
 23  7  1  6  0  0  0
M  END

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 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  6
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 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
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 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

            
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0345    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
 9998.2016 9999.7849    0.0000 C   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
 9999.627010001.2705    0.0000 O   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
 9999.6270 9999.7849    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  1  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
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  1  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
10001.126610001.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.412110001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.841010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555410001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.861710000.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.984510001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 11  2  1  6  0  0  0
  9 13  1  0  0  0  0
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 20 23  1  0  0  0  0
 22  1  1  1  0  0  0
 23  7  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000626

> <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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

> <INCHI_KEY>
KXGVEGMKQFWNSR-LLQZFEROSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.30045298852684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.7912592536666683

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396318179

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.651656794864149

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3511899140388809

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.19679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 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  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
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  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0    8665.9708669.038   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8667.4368669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.1038669.832   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8671.4378669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.7718669.832   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0    8670.1428668.221   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0    8672.7718671.372   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0    8674.1048669.062   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   13                                                            
CONECT    5   19                                                            
CONECT    6   17                                                            
CONECT    7   23                                                            
CONECT    8   20                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    4   19                                             
CONECT   14   13   15   12    3                                             
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17   18    6   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   13    5                                             
CONECT   20   19   16    8   23                                             
CONECT   21   22   25   26   31                                             
CONECT   22   21   23   17    1                                             
CONECT   23   22   24   20    7                                             
CONECT   24   23   25                                                       
CONECT   25   21   24                                                       
CONECT   26   21   28   27                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   32   33                                                  
CONECT   31   21                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000626
HETATM    1  C1  UNL     1      -4.494   0.548   1.956  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.526   0.575   0.756  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.336   0.274  -0.442  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.415   1.377  -0.514  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.287   1.185  -1.671  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.105   0.221  -2.447  1.00  0.00           O  
HETATM    7  O2  UNL     1      -7.324   2.062  -1.925  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.351  -0.216   1.069  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.508  -1.666   1.390  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.116  -2.290   1.173  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.265  -1.102   0.881  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.033  -1.321   0.231  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.976  -2.025   1.188  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.187  -1.243   1.547  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.931  -0.664   0.375  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.638   0.592   0.904  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.561   1.192  -0.102  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.676   2.584   0.046  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.991   0.946  -1.491  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.487   1.076  -1.381  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.963  -0.163  -0.699  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.835  -1.231  -1.789  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.659   0.062   0.001  1.00  0.00           C  
HETATM   24  C21 UNL     1       0.753   0.938  -0.825  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.620   1.052  -0.228  1.00  0.00           C  
HETATM   26  O4  UNL     1      -0.535   1.743   0.982  1.00  0.00           O  
HETATM   27  C23 UNL     1      -1.241  -0.270   0.036  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.632  -0.990  -1.204  1.00  0.00           C  
HETATM   29  H1  UNL     1      -3.950   0.161   2.855  1.00  0.00           H  
HETATM   30  H2  UNL     1      -5.288  -0.207   1.734  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.908   1.540   2.174  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.216   1.661   0.697  1.00  0.00           H  
HETATM   33  H5  UNL     1      -4.873  -0.672  -0.317  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.813   0.385  -1.415  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.875   2.336  -0.639  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.971   1.362   0.442  1.00  0.00           H  
HETATM   37  H9  UNL     1      -8.283   1.915  -1.621  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.851   0.238   1.981  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.275  -2.180   0.811  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.745  -1.797   2.466  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.744  -2.766   2.096  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.140  -3.045   0.379  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.092  -0.542   1.823  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.026  -1.829  -0.752  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.435  -2.267   2.126  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.288  -3.029   0.775  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.964  -0.489   2.340  1.00  0.00           H  
HETATM   48  H20 UNL     1       3.899  -1.963   2.041  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.623  -1.365  -0.090  1.00  0.00           H  
HETATM   50  H22 UNL     1       5.205   0.304   1.802  1.00  0.00           H  
HETATM   51  H23 UNL     1       3.835   1.316   1.146  1.00  0.00           H  
HETATM   52  H24 UNL     1       6.562   0.771   0.021  1.00  0.00           H  
HETATM   53  H25 UNL     1       6.125   2.907  -0.791  1.00  0.00           H  
HETATM   54  H26 UNL     1       5.406   1.653  -2.239  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.309  -0.071  -1.778  1.00  0.00           H  
HETATM   56  H28 UNL     1       3.240   2.002  -0.835  1.00  0.00           H  
HETATM   57  H29 UNL     1       3.078   1.130  -2.421  1.00  0.00           H  
HETATM   58  H30 UNL     1       1.934  -1.053  -2.403  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.701  -1.095  -2.499  1.00  0.00           H  
HETATM   60  H32 UNL     1       2.918  -2.244  -1.402  1.00  0.00           H  
HETATM   61  H33 UNL     1       1.799   0.507   0.997  1.00  0.00           H  
HETATM   62  H34 UNL     1       1.198   1.954  -0.817  1.00  0.00           H  
HETATM   63  H35 UNL     1       0.746   0.601  -1.869  1.00  0.00           H  
HETATM   64  H36 UNL     1      -1.224   1.674  -0.927  1.00  0.00           H  
HETATM   65  H37 UNL     1      -0.925   2.643   0.908  1.00  0.00           H  
HETATM   66  H38 UNL     1      -1.653  -0.340  -2.077  1.00  0.00           H  
HETATM   67  H39 UNL     1      -0.839  -1.760  -1.435  1.00  0.00           H  
HETATM   68  H40 UNL     1      -2.561  -1.591  -1.104  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   27   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   23   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   21   49
CONECT   16   17   50   51
CONECT   17   18   19   52
CONECT   18   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   23
CONECT   22   58   59   60
CONECT   23   24   61
CONECT   24   25   62   63
CONECT   25   26   27   64
CONECT   26   65
CONECT   27   28
CONECT   28   66   67   68
END

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 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  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID	ChEBI
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid	ChEBI
3alpha,12alpha-Dihydroxy-5beta-cholanic acid	ChEBI
7alpha-Deoxycholic acid	ChEBI
Desoxycholic acid	ChEBI
Desoxycholsaeure	ChEBI
Deoxycholate	Kegg
3alpha,12alpha-Dihydroxy-5beta-cholanate	Kegg
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid	Generator
(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oate	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
3a,12a-Dihydroxy-5b-cholanate	Generator
3a,12a-Dihydroxy-5b-cholanic acid	Generator
3Α,12α-dihydroxy-5β-cholanate	Generator
3Α,12α-dihydroxy-5β-cholanic acid	Generator
7a-Deoxycholate	Generator
7a-Deoxycholic acid	Generator
7alpha-Deoxycholate	Generator
7Α-deoxycholate	Generator
7Α-deoxycholic acid	Generator
Desoxycholate	Generator
5b-Cholanic acid-3a,12a-diol	HMDB
5b-Deoxycholate	HMDB
5b-Deoxycholic acid	HMDB
7-Deoxycholate	HMDB
7-Deoxycholic acid	HMDB
Cholerebic	HMDB
Cholorebic	HMDB
Degalol	HMDB
Deoxy-cholate	HMDB
Deoxy-cholic acid	HMDB
Deoxycholatate	HMDB
Deoxycholatic acid	HMDB
Acid, lagodeoxycholic	HMDB
Deoxycholic acid, 5alpha isomer	HMDB
Deoxycholic acid, sodium salt, 12beta-isomer	HMDB
Lagodeoxycholic acid	HMDB
Acid, choleic	HMDB
Deoxycholic acid, 12beta isomer	HMDB
Deoxycholic acid, 3beta-isomer	HMDB
Deoxycholic acid, monoammonium salt	HMDB
12beta-Isomer deoxycholic acid	HMDB
3beta-Isomer deoxycholic acid	HMDB
Acid, 5alpha-isomer deoxycholic	HMDB
Acid, deoxycholic	HMDB
Acid, desoxycholic	HMDB
Deoxycholate, sodium	HMDB
Deoxycholic acid, 12beta-isomer	HMDB
Deoxycholic acid, 5alpha-isomer	HMDB
Deoxycholic acid, monopotassium salt	HMDB
Deoxycholic acid, monosodium salt	HMDB
5alpha-Isomer deoxycholic acid	HMDB
Acid, dihydroxycholanoic	HMDB
Choleic acid	HMDB
Deoxycholic acid, 3beta isomer	HMDB
Deoxycholic acid, disodium salt	HMDB
Deoxycholic acid, magnesium (2:1) salt	HMDB
Dihydroxycholanoic acid	HMDB
Sodium deoxycholate	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

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

CAS Registry Number

83-44-3

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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

InChI Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:28834 )
dihydroxy-5beta-cholanic acid (CHEBI:28834 )
C24 bile acids, alcohols, and derivatives (C04483 )
Cholane and derivatives (C04483 )
C24 bile acids, alcohols, and derivatives (LMST04010040 )

Ontology

Not Available

Erythrocyte (HMDB: HMDB0000626)
Fibroblasts (HMDB: HMDB0000626)

Organ

Intestine (HMDB: HMDB0000626)

Biofluid or Excreta

Non-excretory biofluid

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

Excreta

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

Cellular substructure

Extracellular (HMDB: HMDB0000626)

Intestine (HMDB: HMDB0000626)

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

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Caprae

Domestic goat (FooDB: FOOD00529)

Bovine

Venison

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

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: HMDB0000626)
Inner Membrane Transport (PathBank: SMP0000808)

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

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	171 - 174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.044 mg/mL	Not Available
LogP	3.50	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	200.697	30932474
[M-H]-	Not Available	201.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000202

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.3	ALOGPS
logP	3.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	46.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	191.141	31661259
DarkChem	[M-H]-	191.706	31661259
AllCCS	[M+H]+	200.657	32859911
AllCCS	[M-H]-	198.915	32859911
DeepCCS	[M-2H]-	234.684	30932474
DeepCCS	[M+Na]+	208.649	30932474
AllCCS	[M+H]+	200.7	32859911
AllCCS	[M+H-H2O]+	198.5	32859911
AllCCS	[M+NH4]+	202.6	32859911
AllCCS	[M+Na]+	203.2	32859911
AllCCS	[M-H]-	198.9	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	201.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxycholic 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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	3905.8	Standard polar	33892256
Deoxycholic 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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	3315.4	Standard non polar	33892256
Deoxycholic 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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	3478.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxycholic 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]3C[C@H](O)[C@@]21C	3376.3	Semi standard non polar	33892256
Deoxycholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3366.5	Semi standard non polar	33892256
Deoxycholic acid,1TMS,isomer #3	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]3C[C@H](O)[C@@]21C	3290.7	Semi standard non polar	33892256
Deoxycholic 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]3C[C@H](O)[C@@]21C	3307.6	Semi standard non polar	33892256
Deoxycholic acid,2TMS,isomer #2	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]3C[C@H](O[Si](C)(C)C)[C@@]21C	3308.3	Semi standard non polar	33892256
Deoxycholic acid,2TMS,isomer #3	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]3C[C@H](O[Si](C)(C)C)[C@@]21C	3285.5	Semi standard non polar	33892256
Deoxycholic acid,3TMS,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]3C[C@H](O[Si](C)(C)C)[C@@]21C	3270.4	Semi standard non polar	33892256
Deoxycholic 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]3C[C@H](O)[C@@]21C	3592.5	Semi standard non polar	33892256
Deoxycholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3585.2	Semi standard non polar	33892256
Deoxycholic acid,1TBDMS,isomer #3	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]3C[C@H](O)[C@@]21C	3553.4	Semi standard non polar	33892256
Deoxycholic 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]3C[C@H](O)[C@@]21C	3785.2	Semi standard non polar	33892256
Deoxycholic acid,2TBDMS,isomer #2	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]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3758.6	Semi standard non polar	33892256
Deoxycholic acid,2TBDMS,isomer #3	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]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3775.7	Semi standard non polar	33892256
Deoxycholic acid,3TBDMS,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]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3984.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00os-0119000000-ff101495d4bc6a37fc83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-cc7d539ad02f4039ec09	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholic acid GC-MS (TBDMS_3_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 - Deoxycholic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0006-0009000000-8b9c4803e9cb1d194c2e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0006-0009000000-cccabd9d13ac783b6e31	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0007-2009000000-d7c20760d2074c07af22	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0006-0009000000-269a5d1ed75b71c78ecb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOF	splash10-0007-0009000000-72f1acf9f31f344daaa1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-000x-0008000900-ebb0e6a61bd8f06a21f7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-IT , negative-QTOF	splash10-0002-0009000000-8078ef73008efc65c713	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0009000000-269a5d1ed75b71c78ecb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid LC-ESI-QTOF , negative-QTOF	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 20V, Negative-QTOF	splash10-0006-0009000000-ade8ee412cabab0a5cdd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 30V, Negative-QTOF	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-46347f9ccba012a193b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 40V, Negative-QTOF	splash10-0007-0009000000-7de3b9549dc580acb2af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 30V, Positive-QTOF	splash10-0007-0009000000-72f1acf9f31f344daaa1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 40V, Negative-QTOF	splash10-0007-0009000000-fa7c4f74eaf1bb2e1f57	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-737c78b82fef7180b7ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxycholic acid 20V, Negative-QTOF	splash10-0006-0009000000-eb86d43bab0334d7cfe4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 10V, Positive-QTOF	splash10-056r-0009000000-db8bf3905980e8620f12	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 20V, Positive-QTOF	splash10-056r-0009000000-6a632f1c8fbb19a314cb	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 40V, Positive-QTOF	splash10-014i-4219000000-29a9a2c5d3d148fca202	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-ab9ac299290313e78fe4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 20V, Negative-QTOF	splash10-006x-1009000000-6444232cac6b7a24dd96	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-b2f4c82d34550211259c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 10V, Positive-QTOF	splash10-054o-0019000000-a4dfbb4ad2f96e8ee6db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholic acid 20V, Positive-QTOF	splash10-0adl-4298000000-b6171657518bf9639cbe	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Urine

Tissue Locations

Erythrocyte
Fibroblasts
Intestine

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	11720 (11570-11860) uM	Adult (>18 years old)	Both	Normal	16548228	details
Blood	Detected and Quantified	0.57 +/- 0.35 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.33 +/- 0.06 uM	Adult (>18 years old)	Both	Normal	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected and Quantified	1920.10 +/- 1390.50 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.055 (0.05-0.060) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.43 +/- 0.09 uM	Adult (>18 years old)	Both	Cystic fibrosis	15185309	details
Blood	Detected and Quantified	0.76 +/- 0.26 uM	Children (1-13 years old)	Both	Cystic fibrosis	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	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	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	Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Urine	Detected and Quantified	0.5 (0.1-1.3) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.3 (0.06-0.87) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.509 (0.113 - 1.324) umol/mmol creatinine	Adult (>18 years old)	Both	Primary biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.328 (0.0679 - 0.871) umol/mmol creatinine	Adult (>18 years old)	Both	Primary 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 ]
Irritable bowel syndrome
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Colorectal cancer
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 ] 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 ] 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)
114500 (Colorectal cancer)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

DB03619

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deoxycholic acid

METLIN ID

265

PubChem Compound

222528

PDB ID

Not Available

ChEBI ID

28834

Food Biomarker Ontology

Not Available

VMH ID

DCHAC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

He, Zhiquan. in-situ generation of deoxycholic acid by poultry for Chinese medicine. Faming Zhuanli Shenqing Gongkai Shuomingshu (1993), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Berr F, Stellaard F, Pratschke E, Paumgartner G: Effects of cholecystectomy on the kinetics of primary and secondary bile acids. J Clin Invest. 1989 May;83(5):1541-50. [PubMed:2708522 ]
Yamaga N, Adachi K, Shimizu K, Miyake S, Sumi F, Miyagawa I, Goto H: Bile acids of patients with renal failure receiving chronic hemodialysis. Steroids. 1986 Nov-Dec;48(5-6):427-38. [PubMed:3445292 ]
Stellaard F, Paumgartner G, van Berge Henegouwen GP, van der Werf SD: Determination of deoxycholic acid pool size and input rate using [24-13C]deoxycholic acid and serum sampling. J Lipid Res. 1986 Nov;27(11):1222-5. [PubMed:3559388 ]
Andersen RB, Bruusgaard A: Effect of the common bile acids on the fibrin/fibrinogen fragments in rheumatoid synovial fluid. A possible clue to the ameliorating effect of jaundice in rheumatoid arthritis. Scand J Rheumatol. 1975;4(3):158-64. [PubMed:52191 ]
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 ]
Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43. [PubMed:15300575 ]
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 ]
Heikkinen J, Maentausta O, Tuimala R, Ylostalo P, Janne O: Amniotic fluid bile acids in normal and pathologic pregnancy. Obstet Gynecol. 1980 Jul;56(1):60-4. [PubMed:7383489 ]
Duret G, Delcour AH: Deoxycholic acid blocks vibrio cholerae OmpT but not OmpU porin. J Biol Chem. 2006 Jul 21;281(29):19899-905. Epub 2006 May 2. [PubMed:16670088 ]
Costarelli V, Sanders TA: Plasma deoxycholic acid concentration is elevated in postmenopausal women with newly diagnosed breast cancer. Eur J Clin Nutr. 2002 Sep;56(9):925-7. [PubMed:12209383 ]
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 ]
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 ]
Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. [PubMed:1641875 ]
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 ]

Enzymes

Enzyme Details

1. 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

2. 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

References

Schuetz EG, Strom S, Yasuda K, Lecureur V, Assem M, Brimer C, Lamba J, Kim RB, Ramachandran V, Komoroski BJ, Venkataramanan R, Cai H, Sinal CJ, Gonzalez FJ, Schuetz JD: Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. J Biol Chem. 2001 Oct 19;276(42):39411-8. Epub 2001 Aug 16. [PubMed:11509573 ]

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 ]
Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [PubMed:9458785 ]
Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [PubMed:10101301 ]
Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [PubMed:12092825 ]

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

References

Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829 ]

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

References

Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [PubMed:8045503 ]
Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829 ]

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

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

Showing metabocard for Deoxycholic acid (HMDB0000626)

MOL for HMDB0000626 (Deoxycholic acid)

3D MOL for HMDB0000626 (Deoxycholic acid)

3D SDF for HMDB0000626 (Deoxycholic acid)

3D-SDF for HMDB0000626 (Deoxycholic acid)

PDB for HMDB0000626 (Deoxycholic acid)

3D PDB for HMDB0000626 (Deoxycholic acid)

SMILES for HMDB0000626 (Deoxycholic acid)

INCHI for HMDB0000626 (Deoxycholic acid)

Structure for HMDB0000626 (Deoxycholic acid)

3D Structure for HMDB0000626 (Deoxycholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References

References

References

References