NP-MRD: Showing NP-Card for Deoxycholic acid (NP0000784)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:48 UTC

NP-MRD ID

NP0000784

Secondary Accession Numbers

None

Natural Product 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
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
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 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
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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
 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
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 30 32  2  0  0  0  0
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 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
> <DATABASE_ID>
NP0000784

> <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])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

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 Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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

Not Available

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
Pseudomonas syringae	LOTUS Database	35616633
Selenarctos thibetanus	-	KNApSAcK
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Bos taurus domesticus GMELIN	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792
Myroides sp. SM1	KNApSAcK Database	22123792
Penicillium sp. SA29	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443.

Predicted 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

External Links

HMDB ID

HMDB0000626

DrugBank ID

DB03619

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1234621

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 ]
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 ]
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 ]

Showing NP-Card for Deoxycholic acid (NP0000784)

MOL for NP0000784 (Deoxycholic acid)

3D MOL for NP0000784 (Deoxycholic acid)

3D SDF for NP0000784 (Deoxycholic acid)

3D-SDF for NP0000784 (Deoxycholic acid)

PDB for NP0000784 (Deoxycholic acid)

3D PDB for NP0000784 (Deoxycholic acid)

SMILES for NP0000784 (Deoxycholic acid)

INCHI for NP0000784 (Deoxycholic acid)

Structure for NP0000784 (Deoxycholic acid)

3D Structure for NP0000784 (Deoxycholic acid)