NP-MRD: Showing NP-Card for Bisnorcholic acid (NP0086865)

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Record Information

Version

2.0

Created at

2022-05-11 16:33:10 UTC

Updated at

2022-05-11 16:33:10 UTC

NP-MRD ID

NP0086865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bisnorcholic acid

Description

Bisnorcholic acid, also known as dinorcholate, 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. Bisnorcholic acid was first documented in 1990 (PMID: 2079611). Bisnorcholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219212D          

 32 35  0  0  1  0            999 V2000
    6.8811   -6.9286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8811   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1665   -6.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -8.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -6.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3101   -6.9286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5955   -6.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5955   -8.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -5.6911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0246   -6.5161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3101   -5.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5956   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8092   -5.4362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2942   -6.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8093   -6.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -8.1661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -8.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3200   -4.5865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797   -8.5297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797   -6.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8374   -7.3411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2848   -7.1733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0962   -5.9708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0052   -5.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9140   -4.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6412   -4.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3124   -5.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8789   -4.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4806   -4.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4874   -5.3975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  6 18  1  6  0  0  0
  8 19  1  6  0  0  0
 13 20  1  6  0  0  0
  2 21  1  1  0  0  0
  1 22  1  1  0  0  0
  7 23  1  1  0  0  0
 12 24  1  6  0  0  0
  9 25  1  6  0  0  0
 11 26  1  1  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  6  0  0  0
 15 32  1  6  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    4.0741   -2.1170    1.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365   -1.0395    0.5630 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6408   -0.4164    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3131   -0.8313    1.8257 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1362    0.6167    0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    0.0023    0.6431 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5483    1.1237   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048    1.6319   -0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465    0.9607    0.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1597    0.9333   -0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9675   -0.1032    0.3507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2761   -1.4469    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046   -1.2845    1.0521 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8797   -0.7619    2.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -0.4259    0.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9480   -1.0505   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -0.2448   -0.2002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8105   -1.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115   -1.1001    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910   -1.2515    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2010    0.0626   -0.3353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4965    0.0965    0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724    1.1555    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    1.1339   -0.2619 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1658    2.1521    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723    2.2925    0.0017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0076    2.8891    1.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235   -3.0733    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -2.4085    2.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -1.8093    2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124   -1.5258   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6694    0.4719   -0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720    0.4979    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1016    1.9461    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.7425   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.7370   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369    1.2872   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    1.4395    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756    0.8685   -1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.2238    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -2.1277    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068   -1.8151   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -2.3158    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575   -1.5307    2.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9028   -0.7763   -1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.6871   -1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073   -2.1577   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078   -0.7981   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6440   -1.8881   -1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0642   -0.2896   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457   -2.1400    0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107   -0.6866    1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5434   -1.9322   -0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2067   -1.7908    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2775    0.1889   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6019    0.6646    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8295    2.1185    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4053    1.0096    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0384    1.5125   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    3.1265    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    1.9041    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331    2.9892   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078    3.8574    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 26  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  6
 17 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
  6  2  1  0
  2  1  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
 15  6  1  0
 15  9  1  0
 11 10  1  0
 17 24  1  0
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  1
 10 39  1  6
 26 62  1  6
 27 63  1  0
 25 60  1  0
 25 61  1  0
 24 59  1  6
 23 57  1  0
 23 58  1  0
 21 55  1  6
 22 56  1  0
 20 53  1  0
 20 54  1  0
 19 51  1  0
 19 52  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 11 40  1  1
 12 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
  2 31  1  6
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 32  1  0
M  END


  Mrv0541 02231219212D          

 32 35  0  0  1  0            999 V2000
    6.8811   -6.9286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8811   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1665   -6.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -8.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -6.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3101   -6.9286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.7536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5955   -6.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5955   -8.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -5.6911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0246   -6.5161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3101   -5.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5956   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8092   -5.4362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2942   -6.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8093   -6.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -8.1661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -8.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3200   -4.5865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797   -8.5297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797   -6.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8374   -7.3411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2848   -7.1733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0962   -5.9708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0052   -5.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9140   -4.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6412   -4.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3124   -5.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8789   -4.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4806   -4.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4874   -5.3975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  6 18  1  6  0  0  0
  8 19  1  6  0  0  0
 13 20  1  6  0  0  0
  2 21  1  1  0  0  0
  1 22  1  1  0  0  0
  7 23  1  1  0  0  0
 12 24  1  6  0  0  0
  9 25  1  6  0  0  0
 11 26  1  1  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  6  0  0  0
 15 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086865

> <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)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h11-19,23-25H,4-10H2,1-3H3,(H,26,27)/t11-,12-,13+,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1

> <INCHI_KEY>
BBSJMECOWBMUCF-XPCRKILGSA-N

> <FORMULA>
C22H36O5

> <MOLECULAR_WEIGHT>
380.5182

> <EXACT_MASS>
380.256274262

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.74746665010955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(1S,2S,5R,7S,9R,10R,11S,14R,15S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]propanoic acid

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.8493243086666666

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.512628757527443

> <JCHEM_PKA_STRONGEST_BASIC>
-0.14473213767375726

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
101.61319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisnorcholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      12.845 -12.933   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.845 -14.473   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.511 -12.163   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.511 -15.243   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.177 -12.933   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.177 -14.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.512 -12.933   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.512 -14.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.178 -12.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.178 -15.243   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.846 -10.623   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.846 -12.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.512  -9.853   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.178 -10.623   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.311 -10.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.216 -11.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.311 -12.639   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.844 -15.243   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.653 -15.165   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      15.531  -8.561   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      12.842 -15.922   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      12.842 -11.798   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      16.496 -13.703   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      17.332 -13.390   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      15.113 -11.145   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      16.810  -9.527   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.506  -8.901   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.864  -8.535   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      21.116  -9.345   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      20.307  -7.543   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.697  -8.196   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      19.576 -10.075   0.000  0.00  0.00           H+0
CONECT    1    3    9    2   22                                             
CONECT    2    4   10    1   21                                             
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   18                                                  
CONECT    7    8   12    9   23                                             
CONECT    8    7   10   19                                                  
CONECT    9    1    7   14   25                                             
CONECT   10    8    2                                                       
CONECT   11   13   15   12   26                                             
CONECT   12    7   11   17   24                                             
CONECT   13   11   14   20                                                  
CONECT   14   13    9                                                       
CONECT   15   11   16   27   32                                             
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18    6                                                            
CONECT   19    8                                                            
CONECT   20   13                                                            
CONECT   21    2                                                            
CONECT   22    1                                                            
CONECT   23    7                                                            
CONECT   24   12                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   15   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27                                                            
CONECT   32   15                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
24-Dinor-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-22-Oic acid	ChEBI
Dinorcholic acid	ChEBI
24-Dinor-3a,7a,12a-trihydroxy-5b-cholan-22-Oate	Generator
24-Dinor-3a,7a,12a-trihydroxy-5b-cholan-22-Oic acid	Generator
24-Dinor-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-22-Oate	Generator
24-Dinor-3α,7α,12α-trihydroxy-5β-cholan-22-Oate	Generator
24-Dinor-3α,7α,12α-trihydroxy-5β-cholan-22-Oic acid	Generator
Dinorcholate	Generator
Bisnorcholate	Generator

Chemical Formula

C₂₂H₃₆O₅

Average Mass

380.5182 Da

Monoisotopic Mass

380.25627 Da

IUPAC Name

(2S)-2-[(1S,2S,5R,7S,9R,10R,11S,14R,15S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]propanoic acid

Traditional Name

bisnorcholic 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)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)C(O)=O

InChI Identifier

InChI=1S/C22H36O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h11-19,23-25H,4-10H2,1-3H3,(H,26,27)/t11-,12-,13+,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1

InChI Key

BBSJMECOWBMUCF-XPCRKILGSA-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 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
Steroid acid
3-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

C22 bile acids, alcohols, and derivatives (LMST04050005 )

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	1.71	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-0.14	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	2	ChemAxon
Refractivity	101.61 m³·mol⁻¹	ChemAxon
Polarizability	42.75 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

HMDB0002082

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022836

KNApSAcK ID

Not Available

Chemspider ID

7826644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547705

PDB ID

Not Available

ChEBI ID

145219

Good Scents ID

Not Available

References

General References

Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]

Showing NP-Card for Bisnorcholic acid (NP0086865)

MOL for NP0086865 (Bisnorcholic acid)

3D MOL for NP0086865 (Bisnorcholic acid)

3D SDF for NP0086865 (Bisnorcholic acid)

3D-SDF for NP0086865 (Bisnorcholic acid)

PDB for NP0086865 (Bisnorcholic acid)

3D PDB for NP0086865 (Bisnorcholic acid)

SMILES for NP0086865 (Bisnorcholic acid)

INCHI for NP0086865 (Bisnorcholic acid)

Structure for NP0086865 (Bisnorcholic acid)

3D Structure for NP0086865 (Bisnorcholic acid)