NP-MRD: Showing NP-Card for 1beta-Hydroxycholic acid (NP0086542)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:23:54 UTC

Updated at

2022-05-11 16:23:54 UTC

NP-MRD ID

NP0086542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta-Hydroxycholic acid

Description

1B-Hydroxycholic acid, also known as 1b-hydroxycholate, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. 1B-Hydroxycholic acid is a C24 bile acid in the serum of healthy human fetuses, and an usual urinary bile acid in the neonatal and pediatric periods, also excreted in the urine of pregnant women. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. 1B-Hydroxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 1B-Hydroxycholic acid exists in all living organisms, ranging from bacteria to humans. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302112016262D          

 35 38  0  0  0  0            999 V2000
 9998.2167 9999.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.641710001.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.354710001.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3547 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.504110000.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0750 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9997.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3568 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6417 9999.7949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9291 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5034 9999.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7889 9998.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5034 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2151 9998.9668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2151 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9296 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6441 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.642310000.6257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.927810000.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9278 9999.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6423 9998.9757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.356810000.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3568 9999.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1414 9999.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6263 9999.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.141410000.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.141410001.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.857110001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.570710001.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.000010001.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410002.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.427710001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.857110000.8807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  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
 13  6  1  6  0  0  0
 11  5  1  1  0  0  0
 18  8  1  6  0  0  0
 14 16  1  0  0  0  0
 16  7  1  1  0  0  0
 11 15  1  0  0  0  0
 15  1  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19  2  1  6  0  0  0
 21 15  1  0  0  0  0
 21 10  1  6  0  0  0
 18 22  1  0  0  0  0
 22  9  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 27 35  1  6  0  0  0
 28 29  1  0  0  0  0
 28 34  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 27 23  1  0  0  0  0
 27 26  1  0  0  0  0
 22 24  1  0  0  0  0
 24  4  1  6  0  0  0
 19 23  1  0  0  0  0
 23  3  1  1  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
   -4.7267   -0.2543    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086    0.2740    0.5348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4472    0.3185   -0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7428    1.0476   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8859    0.5709   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3018    1.1614    0.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5584   -0.5813   -0.5721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -0.4470    0.6494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6068   -1.9435    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541   -2.3595    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912   -1.0961    0.3561 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9663   -1.0201   -0.1611 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4673    0.4069    0.0928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5616    1.3921   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699    1.3036   -0.0771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0420    1.7322    1.2186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3941   -0.0935   -0.2427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5615   -0.4973   -1.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.6135   -0.4056 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7669    0.9052   -1.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629   -0.6363   -0.2668 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1369   -0.4904   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7020    0.7929    0.1438 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7944    0.5216    0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    1.6144    0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.8248    0.2635 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5694    2.8877   -0.6322 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -1.3969    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -1.9807    0.6290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2274   -2.3610    1.8229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1175    0.6104    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5194   -0.8990    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -0.8868    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912    1.3484    0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    0.7258   -1.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6676   -0.7412   -1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0179    1.2175   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5156    2.1101   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6619   -1.2789    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1657   -0.3121    1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2801   -2.2735   -0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612   -2.4020    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -3.1204    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627   -2.8437   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811   -0.8529    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454   -1.2199   -1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511    0.5132    1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.1727   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    2.4110   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.9910   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400    2.2680    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    0.3703   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889   -1.1033   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -1.2058   -1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1034   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194    0.8419   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047    1.9182   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532   -1.3060   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -1.3642    0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631   -0.5873   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    1.4452   -0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6089    0.5109    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    1.2025    1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977    2.6381    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287    2.2128    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    3.7478   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601   -2.2797    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0729   -0.7652    1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850   -2.9131    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -3.2136    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 29  1  0
 29 30  1  0
 29 28  1  0
 28 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 19  1  0
 19 20  1  6
 19 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
  8  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
 17  8  1  0
 17 11  1  0
 13 12  1  0
 19 21  1  0
  8 40  1  1
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  1
 12 46  1  6
 29 69  1  6
 30 70  1  0
 28 67  1  0
 28 68  1  0
 21 58  1  6
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  1
 27 66  1  0
 20 55  1  0
 20 56  1  0
 20 57  1  0
 13 47  1  1
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
  2 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  7 39  1  0
M  END


  Mrv1652302112016262D          

 35 38  0  0  0  0            999 V2000
 9998.2167 9999.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.641710001.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.354710001.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3547 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.504110000.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0750 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9997.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3568 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6417 9999.7949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9291 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5034 9999.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7889 9998.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5034 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2151 9998.9668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2151 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9296 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6441 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.642310000.6257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.927810000.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9278 9999.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6423 9998.9757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.356810000.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3568 9999.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1414 9999.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6263 9999.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.141410000.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.141410001.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.857110001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.570710001.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.000010001.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410002.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.427710001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.857110000.8807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  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
 13  6  1  6  0  0  0
 11  5  1  1  0  0  0
 18  8  1  6  0  0  0
 14 16  1  0  0  0  0
 16  7  1  1  0  0  0
 11 15  1  0  0  0  0
 15  1  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19  2  1  6  0  0  0
 21 15  1  0  0  0  0
 21 10  1  6  0  0  0
 18 22  1  0  0  0  0
 22  9  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 27 35  1  6  0  0  0
 28 29  1  0  0  0  0
 28 34  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 27 23  1  0  0  0  0
 27 26  1  0  0  0  0
 22 24  1  0  0  0  0
 24  4  1  6  0  0  0
 19 23  1  0  0  0  0
 23  3  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
UYVVLXVBEQAATF-WAIVXGPNSA-N

> <FORMULA>
C24H40O6

> <MOLECULAR_WEIGHT>
424.5708

> <EXACT_MASS>
424.282489012

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.72250588668707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.1788893836666658

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.503883946263052

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475011783419777

> <JCHEM_PKA_STRONGEST_BASIC>
-0.18794760054227921

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
112.26119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-FEB-20         0                                  
HETATM    1  C   UNK     0    8663.3388666.284   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8665.9988669.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8667.3298668.616   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8667.3298663.979   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0    8662.0088667.061   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8659.3408662.424   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0    8663.3388661.652   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0    8667.3338662.424   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0    8665.9988666.284   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8664.6688663.979   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0    8662.0068665.508   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.6738664.738   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.6738663.198   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.0068662.428   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3358664.738   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3358663.198   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6698662.428   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0028663.198   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9998667.835   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6658667.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.6658665.524   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.9998664.755   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3338667.065   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.3338665.525   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.7978665.049   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.7028666.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.7978667.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8668.7978669.081   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.1338669.851   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8671.4658669.081   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8672.8018669.851   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8674.1338669.081   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0    8672.8018671.391   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0    8667.4658669.851   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0    8670.1338668.311   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   19                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   11                                                            
CONECT    6   13                                                            
CONECT    7   16                                                            
CONECT    8   18                                                            
CONECT    9   22                                                            
CONECT   10   21                                                            
CONECT   11   12    5   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14    6                                                  
CONECT   14   13   16                                                       
CONECT   15   16   11    1   21                                             
CONECT   16   15   17   14    7                                             
CONECT   17   16   18                                                       
CONECT   18   17    8   22                                                  
CONECT   19   20    2   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   15   10                                             
CONECT   22   21   18    9   24                                             
CONECT   23   24   27   19    3                                             
CONECT   24   23   25   22    4                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   28   35   23   26                                             
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28                                                            
CONECT   35   27                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oate	HMDB
1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid	HMDB
1b,3a,7a,12a-Tetrahydroxy-5b-cholanoate	HMDB
1b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid	HMDB
1b-Hydroxycholate	HMDB, Generator
(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB
(1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-Tetrahydroxycholan-24-oic acid	HMDB
(1β,3α,5β,7α,12α)-1,3,7,12-Tetrahydroxycholan-24-oic acid	HMDB
1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic acid	HMDB
1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid	HMDB
1beta-Hydroxycholic acid	HMDB
1β,3α,7α,12α-Tetrahydroxy-5β-cholan-24-oic acid	HMDB
1β,3α,7α,12α-Tetrahydroxy-5β-cholanoic acid	HMDB
1β-Hydroxycholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₆

Average Mass

424.5708 Da

Monoisotopic Mass

424.28249 Da

IUPAC Name

(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1

InChI Key

UYVVLXVBEQAATF-WAIVXGPNSA-N

Experimental Spectra

Not Available

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	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, 252 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, 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	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, 300 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	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, 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	¹³C NMR Spectrum (1D, 176 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, 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 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 tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four 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

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Tetrahydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
1-hydroxysteroid
12-hydroxysteroid
7-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

C24 bile acids, alcohols, and derivatives (LMST04010114 )

Physical Properties

State

Not Available

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
logP	1.34	ALOGPS
logP	1.18	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.26 m³·mol⁻¹	ChemAxon
Polarizability	47.72 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

HMDB0000307

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021934

KNApSAcK ID

Not Available

Chemspider ID

4446981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5296

PubChem Compound

5283893

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1beta-Hydroxycholic acid (NP0086542)

MOL for NP0086542 (1beta-Hydroxycholic acid)

3D MOL for NP0086542 (1beta-Hydroxycholic acid)

3D SDF for NP0086542 (1beta-Hydroxycholic acid)

3D-SDF for NP0086542 (1beta-Hydroxycholic acid)

PDB for NP0086542 (1beta-Hydroxycholic acid)

3D PDB for NP0086542 (1beta-Hydroxycholic acid)

SMILES for NP0086542 (1beta-Hydroxycholic acid)

INCHI for NP0086542 (1beta-Hydroxycholic acid)

Structure for NP0086542 (1beta-Hydroxycholic acid)

3D Structure for NP0086542 (1beta-Hydroxycholic acid)