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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 02:49:06 UTC

HMDB ID

HMDB0000733

Secondary Accession Numbers

HMDB00733

Metabolite Identification

Common Name

Hyodeoxycholic acid

Description

Hyodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

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

Hyodeoxycholic acid.mol
  Mrv1652305271900162D          

 31 34  0  0  0  0            999 V2000
   -2.4296   -0.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -1.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -1.9427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8585   -2.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296   -2.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151   -1.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -2.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0006   -3.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -1.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -1.1177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4283   -0.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2129   -0.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6978   -0.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.3747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4679    1.1594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2647    1.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283    0.1198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4283    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862    0.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    0.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -0.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7151   -1.1177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7151   -0.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    1.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    3.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -1.5302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -0.2927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -1.5302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  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
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  6  0  0  0
 14 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 18 27  2  0  0  0  0
 18 28  1  0  0  0  0
 24 29  1  6  0  0  0
 10 30  1  1  0  0  0
 11 31  1  6  0  0  0
M  END

HMDB0000733
     RDKit          3D
Hyodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.5249   -1.1250   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -0.1297    0.3534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2267    1.2588   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7405    1.4518   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0002    2.8009   -0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9104    2.9868   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3397    3.8684   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.3314    0.8402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4920   -1.6451    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -2.2634    1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.0254    0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9073   -1.1733    0.1613 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7755   -1.8499    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -1.8078    0.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8781   -2.0104    2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.4595    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962   -0.3146    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    1.1826    0.3114 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3963    1.4045    1.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.0307   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.2762   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8046    0.0538   -0.6900 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7513   -0.9767   -1.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.2302   -0.1040 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5159    1.0754   -0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.1182   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406   -0.2601   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5919   -0.8685   -1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -2.1589   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4490   -0.7503   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6351   -1.2159   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6090   -0.1630    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0359    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    1.3452   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1461    0.6564   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1807    1.3048    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6606    4.3444    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    0.4575    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -1.5372    2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -2.3121    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238   -2.9150    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516   -2.8969    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.4136    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -1.8105   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.2664    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3596   -2.8549    1.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049   -2.6437    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -2.9480    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    0.2588    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003   -0.8278    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3945   -0.6793   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    1.4327   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.3578    1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964    2.5434    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8322   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.0153   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    0.9834   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6295   -0.8040   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -0.8924   -2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450   -2.0049   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    0.6901    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    0.8550   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    2.1368   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.7846   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084    1.5253    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -0.1601   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807   -1.8813   -1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738   -0.9207   -1.8888 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  6
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  1
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

Hyodeoxycholic acid.mol
  Mrv1652305271900162D          

 31 34  0  0  0  0            999 V2000
   -2.4296   -0.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -1.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -1.9427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8585   -2.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296   -2.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151   -1.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -2.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0006   -3.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -1.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -1.1177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4283   -0.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2129   -0.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6978   -0.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.3747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4679    1.1594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2647    1.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283    0.1198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4283    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862    0.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    0.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -0.7052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7151   -1.1177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7151   -0.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    1.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    3.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006   -1.5302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -0.2927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -1.5302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  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
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  6  0  0  0
 14 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 18 27  2  0  0  0  0
 18 28  1  0  0  0  0
 24 29  1  6  0  0  0
 10 30  1  1  0  0  0
 11 31  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000733

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/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>
DGABKXLVXPYZII-CDONHWFASA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.688343952749776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.7133055236666674

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.751588312419209

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7910428027078265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6909839223091003

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.27379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000733
     RDKit          3D
Hyodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.5249   -1.1250   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -0.1297    0.3534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2267    1.2588   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7405    1.4518   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0002    2.8009   -0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9104    2.9868   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3397    3.8684   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.3314    0.8402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4920   -1.6451    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -2.2634    1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.0254    0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9073   -1.1733    0.1613 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7755   -1.8499    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -1.8078    0.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8781   -2.0104    2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.4595    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962   -0.3146    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    1.1826    0.3114 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3963    1.4045    1.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.0307   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.2762   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8046    0.0538   -0.6900 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7513   -0.9767   -1.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.2302   -0.1040 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5159    1.0754   -0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.1182   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406   -0.2601   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5919   -0.8685   -1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -2.1589   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4490   -0.7503   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6351   -1.2159   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6090   -0.1630    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0359    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    1.3452   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1461    0.6564   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1807    1.3048    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6606    4.3444    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    0.4575    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -1.5372    2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -2.3121    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238   -2.9150    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516   -2.8969    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.4136    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -1.8105   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.2664    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3596   -2.8549    1.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049   -2.6437    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -2.9480    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    0.2588    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003   -0.8278    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3945   -0.6793   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    1.4327   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.3578    1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964    2.5434    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8322   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.0153   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    0.9834   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6295   -0.8040   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -0.8924   -2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450   -2.0049   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    0.6901    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    0.8550   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    2.1368   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.7846   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084    1.5253    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -0.1601   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807   -1.8813   -1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738   -0.9207   -1.8888 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  6
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  1
 25 62  1  0
 25 63  1  0
 26 64  1  0
 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: Hyodeoxycholic acid.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.535  -1.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.869  -2.086   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.869  -3.626   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.203  -4.396   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.535  -4.396   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.202  -3.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.868  -4.396   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.868  -5.936   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.534  -3.626   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.534  -2.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.799  -1.316   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.264  -1.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.169  -0.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.264   0.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.740   2.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.227   2.563   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.626   4.050   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.114   4.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.651   3.253   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.799   0.224   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.799   1.764   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.534   0.994   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.868   0.224   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.868  -1.316   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.202  -2.086   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.202  -0.546   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.203   3.360   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.512   5.936   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      -1.868  -2.856   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.534  -0.546   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.799  -2.856   0.000  0.00  0.00           H+0
CONECT    1    2   25                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   24   30                                             
CONECT   11   10   12   20   31                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   27   28                                                  
CONECT   19   15                                                            
CONECT   20   14   11   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   10   25   29                                             
CONECT   25   24    1    6   26                                             
CONECT   26   25                                                            
CONECT   27   18                                                            
CONECT   28   18                                                            
CONECT   29   24                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0000733
HETATM    1  C1  UNL     1      -4.525  -1.125  -0.587  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.953  -0.130   0.353  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.227   1.259  -0.205  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.740   1.452  -0.334  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.000   2.801  -0.872  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.910   2.987  -2.108  1.00  0.00           O  
HETATM    7  O2  UNL     1      -6.340   3.868  -0.057  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.589  -0.331   0.840  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.492  -1.645   1.582  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.180  -2.263   1.081  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.424  -1.025   0.769  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.907  -1.173   0.161  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.776  -1.850   1.220  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.232  -1.808   0.948  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.878  -2.010   2.189  1.00  0.00           O  
HETATM   16  C13 UNL     1       3.653  -0.460   0.477  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.096  -0.315   0.152  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.409   1.183   0.311  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.396   1.404   1.694  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.316   2.031  -0.269  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.441   1.276  -1.242  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.805   0.054  -0.690  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.751  -0.977  -1.820  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.445   0.230  -0.104  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.516   1.075  -0.882  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.845   1.118  -0.240  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.441  -0.260  -0.084  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.592  -0.869  -1.417  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.156  -2.159  -0.472  1.00  0.00           H  
HETATM   30  H2  UNL     1      -4.449  -0.750  -1.630  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.635  -1.216  -0.402  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.609  -0.163   1.286  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.868   2.036   0.471  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.840   1.345  -1.250  1.00  0.00           H  
HETATM   35  H7  UNL     1      -6.146   0.656  -1.022  1.00  0.00           H  
HETATM   36  H8  UNL     1      -6.181   1.305   0.670  1.00  0.00           H  
HETATM   37  H9  UNL     1      -5.661   4.344   0.559  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.408   0.457   1.636  1.00  0.00           H  
HETATM   39  H11 UNL     1      -2.364  -1.537   2.675  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.349  -2.312   1.393  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.724  -2.915   1.844  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.352  -2.897   0.184  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.325  -0.414   1.699  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.955  -1.810  -0.733  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.587  -1.266   2.166  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.360  -2.855   1.403  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.605  -2.644   0.308  1.00  0.00           H  
HETATM   48  H20 UNL     1       4.128  -2.948   2.325  1.00  0.00           H  
HETATM   49  H21 UNL     1       3.422   0.259   1.315  1.00  0.00           H  
HETATM   50  H22 UNL     1       5.700  -0.828   0.926  1.00  0.00           H  
HETATM   51  H23 UNL     1       5.394  -0.679  -0.832  1.00  0.00           H  
HETATM   52  H24 UNL     1       6.417   1.433  -0.037  1.00  0.00           H  
HETATM   53  H25 UNL     1       5.395   2.358   1.928  1.00  0.00           H  
HETATM   54  H26 UNL     1       3.696   2.543   0.470  1.00  0.00           H  
HETATM   55  H27 UNL     1       4.817   2.832  -0.877  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.747   2.015  -1.685  1.00  0.00           H  
HETATM   57  H29 UNL     1       4.122   0.983  -2.100  1.00  0.00           H  
HETATM   58  H30 UNL     1       3.630  -0.804  -2.503  1.00  0.00           H  
HETATM   59  H31 UNL     1       1.839  -0.892  -2.420  1.00  0.00           H  
HETATM   60  H32 UNL     1       2.845  -2.005  -1.471  1.00  0.00           H  
HETATM   61  H33 UNL     1       1.552   0.690   0.917  1.00  0.00           H  
HETATM   62  H34 UNL     1       0.483   0.855  -1.960  1.00  0.00           H  
HETATM   63  H35 UNL     1       0.904   2.137  -0.819  1.00  0.00           H  
HETATM   64  H36 UNL     1      -1.483   1.785  -0.850  1.00  0.00           H  
HETATM   65  H37 UNL     1      -0.708   1.525   0.792  1.00  0.00           H  
HETATM   66  H38 UNL     1      -2.149  -0.160  -2.089  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.981  -1.881  -1.463  1.00  0.00           H  
HETATM   68  H40 UNL     1      -0.574  -0.921  -1.889  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   24   44
CONECT   13   14   45   46
CONECT   14   15   16   47
CONECT   15   48
CONECT   16   17   22   49
CONECT   17   18   50   51
CONECT   18   19   20   52
CONECT   19   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   24
CONECT   23   58   59   60
CONECT   24   25   61
CONECT   25   26   62   63
CONECT   26   27   64   65
CONECT   27   28
CONECT   28   66   67   68
END

HMDB0000733
     RDKit          3D
Hyodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.5249   -1.1250   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -0.1297    0.3534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2267    1.2588   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7405    1.4518   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0002    2.8009   -0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9104    2.9868   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3397    3.8684   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.3314    0.8402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4920   -1.6451    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -2.2634    1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.0254    0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9073   -1.1733    0.1613 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7755   -1.8499    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -1.8078    0.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8781   -2.0104    2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.4595    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962   -0.3146    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    1.1826    0.3114 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3963    1.4045    1.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.0307   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.2762   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8046    0.0538   -0.6900 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7513   -0.9767   -1.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.2302   -0.1040 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5159    1.0754   -0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.1182   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406   -0.2601   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5919   -0.8685   -1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -2.1589   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4490   -0.7503   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6351   -1.2159   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6090   -0.1630    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0359    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    1.3452   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1461    0.6564   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1807    1.3048    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6606    4.3444    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    0.4575    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -1.5372    2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -2.3121    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238   -2.9150    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516   -2.8969    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.4136    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -1.8105   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.2664    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3596   -2.8549    1.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049   -2.6437    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -2.9480    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    0.2588    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003   -0.8278    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3945   -0.6793   -0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    1.4327   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.3578    1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964    2.5434    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8322   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.0153   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    0.9834   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6295   -0.8040   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -0.8924   -2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450   -2.0049   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    0.6901    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    0.8550   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    2.1368   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.7846   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084    1.5253    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -0.1601   -2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807   -1.8813   -1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738   -0.9207   -1.8888 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
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  6
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  1
 25 62  1  0
 25 63  1  0
 26 64  1  0
 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
Hyodeoxycholate	Generator
3a,6a-Dihydroxy-5b-cholan-24-Oate	HMDB
3a,6a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
3a,6a-Dihydroxy-5b-cholanate	HMDB
3a,6a-Dihydroxy-5b-cholanic acid	HMDB
3a,6a-Dihydroxy-5b-cholanoate	HMDB
3a,6a-Dihydroxy-5b-cholanoic acid	HMDB
6a-Hydroxylithocholate	HMDB
6a-Hydroxylithocholic acid	HMDB
7-Deoxyhyocholate	HMDB
7-Deoxyhyocholic acid	HMDB
a-Hyodeoxycholate	HMDB
a-Hyodeoxycholic acid	HMDB
alpha-Hyodeoxycholate	HMDB
alpha-Hyodeoxycholic acid	HMDB
Hyodesoxycholate	HMDB
Hyodesoxycholic acid	HMDB
Iodeoxycholate	HMDB
Iodeoxycholic acid	HMDB
3,6-Dihydroxy-5alpha-cholanoic acid	HMDB
NaHDC compound	HMDB
Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomer	HMDB
Hyodeoxycholic acid, (3alpha,6beta)-isomer	HMDB
Hyodeoxycholic acid, sodium salt	HMDB
Murideoxycholic acid	HMDB
Sodium hyodeoxycholate	HMDB
(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
Hyodeoxycholic acid	MeSH

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

83-49-8

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C

InChI Identifier

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

DGABKXLVXPYZII-CDONHWFASA-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
6-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

Not Available

Ontology

Physiological effect

Health effect

Primary biliary cirrhosis (HMDB: HMDB0000733)
Cirrhosis (PMID: 1112456)
Jaundice (PMID: 1112456)
Chronic hepatitis (PMID: 1112456)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Urine (PMID: 2621422)
Feces (PMID: 31643938)

Non-excretory biofluid

Blood (PMID: 2621422)
Bile (PMID: 31643938)

Blood (HMDB: HMDB0000733)
Urine (HMDB: HMDB0000733)

Cellular substructure

Extracellular (HMDB: HMDB0000733)

Organ

Tissue substructure

Hepatic tissue (HMDB: HMDB0000733)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000733)

Source

Endogenous

Endogenous (HMDB: HMDB0000733)

Animal

Animal (HMDB: HMDB0000733)

Exogenous

Food

Food (HMDB: HMDB0000733)

Animal origin

Bovine

Swine

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

Poultry

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

Lagomorph

Venison

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

Equine

Horse (FooDB: FOOD00378)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Caprae

Domestic goat (FooDB: FOOD00529)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000733)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000733)

Cellular process

Cell signaling (HMDB: HMDB0000733)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000733)

Role

Biological role

Molecular messenger

Signaling molecule (HMDB: HMDB0000733)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000733)

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 mg/mL	Not Available
LogP	3.08	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.71	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-2.7	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	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.69 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]+	193.731	31661259
DarkChem	[M-H]-	185.703	31661259
AllCCS	[M+H]+	201.157	32859911
AllCCS	[M-H]-	198.892	32859911
DeepCCS	[M-2H]-	236.057	30932474
DeepCCS	[M+Na]+	210.747	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	199.0	32859911
AllCCS	[M+NH4]+	203.1	32859911
AllCCS	[M+Na]+	203.7	32859911
AllCCS	[M-H]-	198.9	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	201.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hyodeoxycholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C	3499.6	Standard polar	33892256
Hyodeoxycholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C	3310.2	Standard non polar	33892256
Hyodeoxycholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C	3503.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hyodeoxycholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3344.3	Semi standard non polar	33892256
Hyodeoxycholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3362.1	Semi standard non polar	33892256
Hyodeoxycholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3408.0	Semi standard non polar	33892256
Hyodeoxycholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3277.4	Semi standard non polar	33892256
Hyodeoxycholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3328.0	Semi standard non polar	33892256
Hyodeoxycholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3331.1	Semi standard non polar	33892256
Hyodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3286.8	Semi standard non polar	33892256
Hyodeoxycholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3606.4	Semi standard non polar	33892256
Hyodeoxycholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3562.7	Semi standard non polar	33892256
Hyodeoxycholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3622.4	Semi standard non polar	33892256
Hyodeoxycholic 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]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3745.2	Semi standard non polar	33892256
Hyodeoxycholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3808.9	Semi standard non polar	33892256
Hyodeoxycholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3764.9	Semi standard non polar	33892256
Hyodeoxycholic 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]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3944.8	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 - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-0329000000-58d5a781e1d72501a6fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1100290000-3298b2503a68dd31087e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyodeoxycholic 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 - Hyodeoxycholic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0006-0009000000-1a7a7cb68338f6eb3692	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0006-0019000000-7ac011fa76fe71b48725	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0006-0009000000-77087c5c31c768755c6c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 35V, Positive-QTOF	splash10-0002-5910000000-e85c0f620f0f33eda383	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 35V, Positive-QTOF	splash10-0002-2900000000-60e4234bfb052d491945	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOF	splash10-0006-2219000000-5b9c1050cbb76dafa745	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOF	splash10-0006-2219000000-be669783febc610d32a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOF	splash10-0006-0009000000-ba6aa3d13b20ed0d0c09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 30V, Negative-QTOF	splash10-0006-0009000000-34256fe4b0144e1f191b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOF	splash10-0006-2219000000-815553fc5ecb67a781b4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 30V, Negative-QTOF	splash10-0006-0009000000-8753654f95e151222293	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOF	splash10-0006-0009000000-30ddec6babbef6e84fde	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Positive-QTOF	splash10-056r-0009000000-581fe3701cfd4409cf1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOF	splash10-056r-0009000000-9218797d27b939f6059a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Positive-QTOF	splash10-02vl-1219000000-acd8de6ea11917fdc1bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Negative-QTOF	splash10-006x-0009000000-f969293bf286459bff3f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Negative-QTOF	splash10-00dl-0009000000-c32f7dbb58c16bc8f793	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-a8bee4058c100d760c3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Positive-QTOF	splash10-054o-0009000000-79e7c3afd290f34646cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOF	splash10-0a4i-3159000000-20e08d1a7b218eb91ebd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Positive-QTOF	splash10-0a4j-9681000000-7db68edc57414ccf438e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-7eba834115ee2c679208	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Negative-QTOF	splash10-006x-0009000000-375fefa884fafe6b05bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOF	splash10-000g-2009000000-f58a3057b3e321a1006c	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.1 (0.0-0.2) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.0056 (0.0-0.011) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

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

109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022211

KNApSAcK ID

Not Available

Chemspider ID

8139282

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hyodeoxycholic acid

METLIN ID

5701

PubChem Compound

9963687

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Eyssen, H. J.; De Pauw, G.; Van Eldere, J. Formation of hyodeoxycholic acid from muricholic acid and hyocholic acid by an unidentified Gram-positive rod termed HDCA-1 isolated from rat intestinal microflora. Applied and Environmental Microbiology (1999),

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Radominska A, Comer KA, Zimniak P, Falany J, Iscan M, Falany CN: Human liver steroid sulphotransferase sulphates bile acids. Biochem J. 1990 Dec 15;272(3):597-604. [PubMed:2268288 ]
Pillot T, Ouzzine M, Fournel-Gigleux S, Lafaurie C, Radominska A, Burchell B, Siest G, Magdalou J: Glucuronidation of hyodeoxycholic acid in human liver. Evidence for a selective role of UDP-glucuronosyltransferase 2B4. J Biol Chem. 1993 Dec 5;268(34):25636-42. [PubMed:8244999 ]
Fournel-Gigleux S, Sutherland L, Sabolovic N, Burchell B, Siest G: Stable expression of two human UDP-glucuronosyltransferase cDNAs in V79 cell cultures. Mol Pharmacol. 1991 Feb;39(2):177-83. [PubMed:1847492 ]
Summerfield JA, Billing BH, Shackleton CH: Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man. Biochem J. 1976 Feb 15;154(2):507-16. [PubMed:938463 ]
Marschall HU, Matern H, Egestad B, Matern S, Sjovall S: 6 alpha-glucuronidation of hyodeoxycholic acid by human liver, kidney and small bowel microsomes. Biochim Biophys Acta. 1987 Sep 25;921(2):392-7. [PubMed:2820501 ]
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 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

Reactions

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

Enzyme Details

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

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

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

Showing metabocard for Hyodeoxycholic acid (HMDB0000733)

MOL for HMDB0000733 (Hyodeoxycholic acid)

3D MOL for HMDB0000733 (Hyodeoxycholic acid)

3D SDF for HMDB0000733 (Hyodeoxycholic acid)

3D-SDF for HMDB0000733 (Hyodeoxycholic acid)

PDB for HMDB0000733 (Hyodeoxycholic acid)

3D PDB for HMDB0000733 (Hyodeoxycholic acid)

SMILES for HMDB0000733 (Hyodeoxycholic acid)

INCHI for HMDB0000733 (Hyodeoxycholic acid)

Structure for HMDB0000733 (Hyodeoxycholic acid)

3D Structure for HMDB0000733 (Hyodeoxycholic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

Transporters

References

References