NP-MRD: Showing NP-Card for 3a,6a,7b-Trihydroxy-5b-cholanoic acid (NP0001302)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:44:50 UTC

NP-MRD ID

NP0001302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,6a,7b-Trihydroxy-5b-cholanoic acid

Description

3A,6a,7b-Trihydroxy-5b-cholanoic acid is an unusual trihydroxy bile acid found in the urine of healthy humans, mainly in newborns (PMID 3769218 ). 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, 6, 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

3a,6a,7b-Trihydroxy-5b-cholanoic acid.mol
  Mrv1652305261923582D          

 33 36  0  0  0  0            999 V2000
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M  END

HMDB0000364
     RDKit          3D
3a,6a,7b-Trihydroxy-5b-cholanoic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.2451   -1.3194   -1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

3a,6a,7b-Trihydroxy-5b-cholanoic acid.mol
  Mrv1652305261923582D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0001302

> <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@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
DKPMWHFRUGMUKF-NTPBNISXSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.5714

> <EXACT_MASS>
408.28757439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.09662171543261

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.716355646666667

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.6233491959118

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595941876165357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.69104497552095

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
110.55829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000364
     RDKit          3D
3a,6a,7b-Trihydroxy-5b-cholanoic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.2451   -1.3194   -1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101   -0.2907   -0.5975 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2186   -0.7827    0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944   -1.1169    0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873    0.0229    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9878    0.4053   -0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0493    0.7652    1.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.4059   -0.6395 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5000    1.1570   -1.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    1.2421   -2.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.9025   -0.9435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0027    0.6472   -0.8952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4537   -0.0917    0.3290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5424   -1.2115    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503   -0.5903    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403   -0.2699   -0.5136 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0959   -1.3709   -1.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.4531    0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0892   -1.0868   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4399    1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9272   -1.3496    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466   -0.0863    1.9915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2139   -0.4700    3.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    0.9131    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6880    0.8256    0.2367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9110    2.0594   -0.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5234    2.6925    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495    1.9545   -0.9361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1590    2.2550   -2.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3711   -1.4595   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480   -2.3316   -1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747   -1.0336   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    0.5268   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858   -1.7423    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -0.0410    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -1.9305    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -1.4879    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6259    1.6356    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474    1.2299    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8687    2.2008   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0655    0.6995   -2.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7319    0.5394   -3.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7246    2.2521   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    1.7491   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    0.0894   -1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172    0.6354    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -1.9793   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879   -1.6517    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575    0.3859    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -1.1646    1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -2.3752   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -1.1269   -2.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -1.3963   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112   -0.3144   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -1.7299   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2727   -1.7612   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087   -1.2825    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1765   -2.4547    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3755   -2.1986    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3797   -1.2047    0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    0.3369    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8135   -1.2585    3.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3118    0.7558    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5225    1.9500    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6205    0.7661   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306    2.8034   -0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497    3.0990    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    2.7949   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337    3.1565   -2.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  6
 26 66  1  6
 27 67  1  0
 28 68  1  1
 29 69  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3a,6a,7b-Trihydroxy-5b-cholanoic acid.mol         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.581  -3.972   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.581  -2.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.247  -1.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.247  -4.742   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.913  -3.972   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.580  -4.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.754  -3.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.754  -2.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.088  -1.662   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -2.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.458  -0.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.552   0.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.028   1.819   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.939   2.908   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.338   4.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.825   4.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.535   2.139   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.088  -0.122   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.088   1.418   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.754   0.648   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.580  -0.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.580  -1.662   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.913  -2.432   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.913  -0.892   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.224   6.282   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.914   3.705   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.088  -4.742   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.580  -6.282   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.914  -4.742   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.913  -5.512   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.580  -3.202   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.754  -0.892   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.088  -3.202   0.000  0.00  0.00           H+0
CONECT    1    2    4   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   30                                             
CONECT    6    5    7   28                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   22   32                                             
CONECT    9    8   10   18   33                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   31                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    7                                                            
CONECT   28    6                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31   22                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000364
HETATM    1  C1  UNL     1       4.245  -1.319  -1.605  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.910  -0.291  -0.597  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.219  -0.783   0.800  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.694  -1.117   0.996  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.587   0.023   0.767  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.988   0.405  -0.361  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.049   0.765   1.861  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.632   0.406  -0.639  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.500   1.157  -1.975  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.016   1.242  -2.264  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.436   0.903  -0.943  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.003   0.647  -0.895  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.454  -0.092   0.329  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.542  -1.212   0.699  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.850  -0.590   0.865  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.340  -0.270  -0.514  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.096  -1.371  -1.512  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.889  -0.453   0.140  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.089  -1.087  -1.234  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.410  -1.440   1.149  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.927  -1.350   1.194  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.247  -0.086   1.992  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.214  -0.470   3.339  1.00  0.00           O  
HETATM   24  C21 UNL     1      -4.179   0.913   1.690  1.00  0.00           C  
HETATM   25  C22 UNL     1      -3.688   0.826   0.237  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.911   2.059  -0.030  1.00  0.00           C  
HETATM   27  O4  UNL     1      -2.523   2.693   1.176  1.00  0.00           O  
HETATM   28  C24 UNL     1      -1.749   1.954  -0.936  1.00  0.00           C  
HETATM   29  O5  UNL     1      -2.159   2.255  -2.255  1.00  0.00           O  
HETATM   30  H1  UNL     1       5.371  -1.460  -1.572  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.848  -2.332  -1.384  1.00  0.00           H  
HETATM   32  H3  UNL     1       4.075  -1.034  -2.663  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.699   0.527  -0.765  1.00  0.00           H  
HETATM   34  H5  UNL     1       3.686  -1.742   1.014  1.00  0.00           H  
HETATM   35  H6  UNL     1       3.961  -0.041   1.582  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.939  -1.930   0.289  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.761  -1.488   2.043  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.626   1.636   2.146  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.647   1.230   0.136  1.00  0.00           H  
HETATM   40  H11 UNL     1       2.869   2.201  -1.866  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.066   0.699  -2.783  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.732   0.539  -3.068  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.725   2.252  -2.622  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.680   1.749  -0.240  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.323   0.089  -1.822  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.417   0.635   1.191  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.561  -1.979  -0.073  1.00  0.00           H  
HETATM   48  H19 UNL     1      -0.888  -1.652   1.656  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.657   0.386   1.403  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.486  -1.165   1.511  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.305  -2.375  -1.126  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.712  -1.127  -2.426  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.058  -1.396  -1.912  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.311  -0.314  -2.010  1.00  0.00           H  
HETATM   55  H26 UNL     1      -4.018  -1.730  -1.218  1.00  0.00           H  
HETATM   56  H27 UNL     1      -2.273  -1.761  -1.493  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.009  -1.283   2.159  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.177  -2.455   0.761  1.00  0.00           H  
HETATM   59  H30 UNL     1      -5.376  -2.199   1.734  1.00  0.00           H  
HETATM   60  H31 UNL     1      -5.380  -1.205   0.203  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.226   0.337   1.736  1.00  0.00           H  
HETATM   62  H33 UNL     1      -5.814  -1.259   3.417  1.00  0.00           H  
HETATM   63  H34 UNL     1      -3.312   0.756   2.394  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.522   1.950   1.882  1.00  0.00           H  
HETATM   65  H36 UNL     1      -4.621   0.766  -0.377  1.00  0.00           H  
HETATM   66  H37 UNL     1      -3.631   2.803  -0.489  1.00  0.00           H  
HETATM   67  H38 UNL     1      -1.650   3.099   1.040  1.00  0.00           H  
HETATM   68  H39 UNL     1      -1.040   2.795  -0.670  1.00  0.00           H  
HETATM   69  H40 UNL     1      -1.934   3.157  -2.531  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    8   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    6    7
CONECT    7   38
CONECT    8    9   16   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   16   44
CONECT   12   13   28   45
CONECT   13   14   18   46
CONECT   14   15   47   48
CONECT   15   16   49   50
CONECT   16   17
CONECT   17   51   52   53
CONECT   18   19   20   25
CONECT   19   54   55   56
CONECT   20   21   57   58
CONECT   21   22   59   60
CONECT   22   23   24   61
CONECT   23   62
CONECT   24   25   63   64
CONECT   25   26   65
CONECT   26   27   28   66
CONECT   27   67
CONECT   28   29   68
CONECT   29   69
END

HMDB0000364
     RDKit          3D
3a,6a,7b-Trihydroxy-5b-cholanoic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.2451   -1.3194   -1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101   -0.2907   -0.5975 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2186   -0.7827    0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944   -1.1169    0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873    0.0229    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9878    0.4053   -0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0493    0.7652    1.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.4059   -0.6395 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5000    1.1570   -1.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    1.2421   -2.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.9025   -0.9435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0027    0.6472   -0.8952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4537   -0.0917    0.3290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5424   -1.2115    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503   -0.5903    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403   -0.2699   -0.5136 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0959   -1.3709   -1.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.4531    0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0892   -1.0868   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4399    1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9272   -1.3496    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466   -0.0863    1.9915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2139   -0.4700    3.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    0.9131    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6880    0.8256    0.2367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9110    2.0594   -0.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5234    2.6925    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495    1.9545   -0.9361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1590    2.2550   -2.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3711   -1.4595   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480   -2.3316   -1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747   -1.0336   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    0.5268   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858   -1.7423    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -0.0410    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -1.9305    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -1.4879    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6259    1.6356    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474    1.2299    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8687    2.2008   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0655    0.6995   -2.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7319    0.5394   -3.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7246    2.2521   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    1.7491   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    0.0894   -1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172    0.6354    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -1.9793   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879   -1.6517    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575    0.3859    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -1.1646    1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -2.3752   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -1.1269   -2.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -1.3963   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112   -0.3144   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -1.7299   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2727   -1.7612   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087   -1.2825    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1765   -2.4547    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3755   -2.1986    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3797   -1.2047    0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    0.3369    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8135   -1.2585    3.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3118    0.7558    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5225    1.9500    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6205    0.7661   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306    2.8034   -0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497    3.0990    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    2.7949   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337    3.1565   -2.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  6
 26 66  1  6
 27 67  1  0
 28 68  1  1
 29 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oic acid	ChEBI
Omega-mca	ChEBI
Omega-muricholic acid	Kegg
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oate	Generator
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oate	Generator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oate	Generator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oic acid	Generator
Omega-muricholate	Generator
3a,6a,7b-Trihydroxy-5b-cholanoate	Generator
3a,6a,7b-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,6a,7b-Trihydroxy-5b-cholan-24-Oic acid	HMDB
W-Muricholate	HMDB
W-Muricholic acid	HMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer	HMDB
Trihydroxy-5 alpha-cholanoic acid	HMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid	HMDB
alpha-Muricholic acid	HMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer	HMDB
3,6,7-Trihydroxy-5-cholanoic acid	HMDB
Muricholic acid, sodium salt	HMDB
beta-Muricholic acid	HMDB
Hyocholic acid	HMDB
Muricholic acid	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Mass

408.5714 Da

Monoisotopic Mass

408.28757 Da

IUPAC Name

(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

6830-03-1

SMILES

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

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1

InChI Key

DKPMWHFRUGMUKF-NTPBNISXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, 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	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	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	¹³C NMR Spectrum (1D, 151 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	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:81299 )
C24 bile acids, alcohols, and derivatives (LMST04010065 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.72	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.56 m³·mol⁻¹	ChemAxon
Polarizability	47.1 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

HMDB0000364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021983

KNApSAcK ID

Not Available

Chemspider ID

4446939

KEGG Compound ID

C17727

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5353

PubChem Compound

5283851

PDB ID

Not Available

ChEBI ID

81299

Good Scents ID

Not Available

References

General References

Nakashima T, Sano A, Seto Y, Nakajima T, Nakagawa Y, Okuno T, Takino T, Hasegawa T: Unusual trihydroxy bile acids in the urine of healthy humans. Clin Chim Acta. 1986 Oct 15;160(1):47-53. [PubMed:3769218 ]

Showing NP-Card for 3a,6a,7b-Trihydroxy-5b-cholanoic acid (NP0001302)

MOL for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

3D MOL for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

3D SDF for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

3D-SDF for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

PDB for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

3D PDB for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

SMILES for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

INCHI for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

Structure for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)

3D Structure for NP0001302 (3a,6a,7b-Trihydroxy-5b-cholanoic acid)