NP-MRD: Showing NP-Card for Hyodeoxycholic acid (NP0000095)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-04-19 09:57:57 UTC

NP-MRD ID

NP0000095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hyodeoxycholic acid

Description

Hyodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on 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>
NP0000095

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-19	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-19	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus domesticus GMELIN	Animalia	KNApSAcK
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	-	KNApSAcK

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

Physical Properties

State

Solid

Experimental 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., 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	0.015 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

External Links

HMDB ID

HMDB0000733

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022211

KNApSAcK ID

C00030498

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

Good Scents ID

rw1015631

References

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 ]

Showing NP-Card for Hyodeoxycholic acid (NP0000095)

MOL for NP0000095 (Hyodeoxycholic acid)

3D MOL for NP0000095 (Hyodeoxycholic acid)

3D SDF for NP0000095 (Hyodeoxycholic acid)

3D-SDF for NP0000095 (Hyodeoxycholic acid)

PDB for NP0000095 (Hyodeoxycholic acid)

3D PDB for NP0000095 (Hyodeoxycholic acid)

SMILES for NP0000095 (Hyodeoxycholic acid)

INCHI for NP0000095 (Hyodeoxycholic acid)

Structure for NP0000095 (Hyodeoxycholic acid)

3D Structure for NP0000095 (Hyodeoxycholic acid)