NP-MRD: Showing NP-Card for N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine (NP0086999)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-05-11 16:36:56 UTC

Updated at

2022-05-11 16:36:56 UTC

NP-MRD ID

NP0086999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine

Description

N-[(3a,5b,7a,12a)-3,7-dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-Glycine, also known as cholane glycine derivative, belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. N-[(3a,5b,7a,12a)-3,7-dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-Glycine is an extremely weak basic (essentially neutral) compound (based on its pKa). It was first documented in 1987 (PMID: 3584362). In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895).

Structure

MOL 3D MOL SDF PDB SMILES InChI

19-norepiandrosterone.mol
  Mrv0541 02231219342D          

 38 41  0  0  0  0            999 V2000
    3.9215    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110    2.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    3.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    3.1209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219   -2.8080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0219   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3074   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3074   -3.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -2.8080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8785   -3.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -2.8080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1640   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -1.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -0.4906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5900    0.2941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4049    0.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005    1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -0.7455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3633    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -0.3330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8785   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8785   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -1.9830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5929   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640    0.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8785    0.9045    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4660    1.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910    0.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    1.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0346    0.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -3.6330    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  2  0  0  0  0
 31 34  1  0  0  0  0
 30 31  1  0  0  0  0
 25 30  1  6  0  0  0
 21 35  2  0  0  0  0
 12 36  1  6  0  0  0
  6 37  1  6  0  0  0
 10 38  1  1  0  0  0
  2 21  1  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
    2.5642   -2.9157   -1.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176   -1.4944   -1.5671 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9004   -0.8643   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529   -0.6322   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7274   -0.0105   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768    0.2161   -1.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3863    0.3108    1.1561 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6983    0.9029    1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2464    1.1778    2.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6410    0.9267    3.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4996    1.7450    2.5487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621   -0.5827   -0.9215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6852    0.7553   -1.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    1.4308   -1.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4069    0.5732   -0.6851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8436    0.7407   -0.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5102    1.4812   -1.7289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1818    2.8371   -1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9757    1.2337   -1.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5853    0.9898   -0.3745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8163    2.2634    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5724    1.9219    1.6415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7369    3.0130    2.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9807    0.8049    2.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6820    0.2568    1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9070   -0.0941    0.4184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7514   -1.3849    0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6626   -0.4827   -0.3584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9463   -1.6257    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661   -1.6932    0.0542 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0389   -1.1703    1.2609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -2.4027    2.0794 S   0  0  1  0  0  6  0  0  0  0  0  0
    2.2800   -2.0926    2.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -2.6029    3.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -3.8769    1.2702 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.8369   -1.0350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2400   -1.2247   -2.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497   -3.3792   -1.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8958   -3.1726   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674   -3.5062   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3058   -1.4477   -2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9342    0.1254   -1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6753   -1.4804   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328   -1.5264    0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7207    0.0910    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8822    0.1011    2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932    0.2799    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6408    1.8829    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2996    1.4140    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749   -0.3743    0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4409    1.4025   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    0.5372   -2.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    1.6271   -2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492    2.4504   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    0.7321    0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0493    1.4294    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1198    1.1628   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815    3.3919   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656    2.1731   -2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002    0.4420   -2.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6299    0.6078   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5209    2.8727   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346    2.8769    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6042    1.6107    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8187    2.7037    3.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -0.0557    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    1.1030    3.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099    0.9818    2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5372   -0.6963    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7668   -1.0616    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7593   -1.8597   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -2.0269    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253   -0.8193   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611   -2.5777   -0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446   -1.7346    1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1290   -2.7238   -0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -4.2353    1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065   -0.3443   -3.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -1.4894   -2.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3791   -2.0462   -2.8328 H   0  0  0  0  0  0  0  0  0  0  0  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  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 32 31  1  6
 32 35  1  0
 32 33  2  0
 32 34  2  0
 30 36  1  0
 36 37  1  6
 36 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 12  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
 26 20  1  0
 16 28  1  0
 19 20  1  0
 15 36  1  0
 20 61  1  6
 21 62  1  0
 21 63  1  0
 22 64  1  6
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  6
 29 74  1  0
 29 75  1  0
 30 76  1  6
 35 77  1  0
 37 78  1  0
 37 79  1  0
 37 80  1  0
 12 50  1  1
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  1
 16 56  1  1
 17 57  1  6
 18 58  1  0
 19 59  1  0
 19 60  1  0
  2 41  1  6
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
 11 49  1  0
M  END

19-norepiandrosterone.mol
  Mrv0541 02231219342D          

 38 41  0  0  0  0            999 V2000
    3.9215    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110    2.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    3.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    3.1209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219   -2.8080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0219   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3074   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3074   -3.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -2.8080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8785   -3.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -2.8080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1640   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -1.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -0.4906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5900    0.2941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4049    0.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7005    1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -0.7455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3633    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640   -0.3330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8785   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8785   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -1.9830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5929   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640    0.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8785    0.9045    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4660    1.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910    0.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    1.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0346    0.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -3.6330    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  2  0  0  0  0
 31 34  1  0  0  0  0
 30 31  1  0  0  0  0
 25 30  1  6  0  0  0
 21 35  2  0  0  0  0
 12 36  1  6  0  0  0
  6 37  1  6  0  0  0
 10 38  1  1  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](OS(O)(=O)=O)[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO9S/c1-14(4-7-22(30)27-13-23(31)32)17-5-6-18-24-19(12-21(26(17,18)3)36-37(33,34)35)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-29H,4-13H2,1-3H3,(H,27,30)(H,31,32)(H,33,34,35)/t14-,15+,16-,17-,18?,19?,20-,21+,24?,25+,26-/m1/s1

> <INCHI_KEY>
JZLKXIMBAHDSBJ-NLKBZSSJSA-N

> <FORMULA>
C26H43NO9S

> <MOLECULAR_WEIGHT>
545.686

> <EXACT_MASS>
545.265852669

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
57.21147989679887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
0.030601251154580792

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.7733120728410596

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1861693787888745

> <JCHEM_PKA_STRONGEST_BASIC>
-0.24240961317578857

> <JCHEM_POLAR_SURFACE_AREA>
170.45999999999998

> <JCHEM_REFRACTIVITY>
133.5846

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 19-norepiandrosterone.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       7.320   5.585   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.247   3.906   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.768   4.147   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.351   6.782   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.841   5.826   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -7.508  -5.242   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.508  -3.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.174  -2.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.174  -6.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.840  -5.242   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.507  -6.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.173  -5.242   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.173  -3.702   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.839  -2.932   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.626  -3.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.531  -2.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.626  -0.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.101   0.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.622   0.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.174   2.227   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.695   2.468   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.071   1.693   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.839  -1.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.678   0.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.173  -0.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.507  -1.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.507  -2.932   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.840  -3.702   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.840  -2.162   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.173   0.918   0.000  0.00  0.00           O+0
HETATM   31  S   UNK     0      -3.507   1.688   0.000  0.00  0.00           S+0
HETATM   32  O   UNK     0      -2.737   3.022   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.277   0.355   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.840   2.458   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.665   1.272   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.839  -6.012   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -8.841  -6.012   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0      -4.840  -6.782   0.000  0.00  0.00           H+0
CONECT    1    3    4    5                                                  
CONECT    2    3   21                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    9   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7   28                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   28   38                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   35    2                                                  
CONECT   22   18                                                            
CONECT   23   17   14   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   13   28                                                  
CONECT   28   27    8   10   29                                             
CONECT   29   28                                                            
CONECT   30   31   25                                                       
CONECT   31   32   33   34   30                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   21                                                            
CONECT   36   12                                                            
CONECT   37    6                                                            
CONECT   38   10                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulphooxy)cholan-24-yl]-glycine	Generator
Cholane glycine derivative	HMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetic acid	HMDB

Chemical Formula

C₂₆H₄₃NO₉S

Average Mass

545.6860 Da

Monoisotopic Mass

545.26585 Da

IUPAC Name

2-[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](OS(O)(=O)=O)[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO9S/c1-14(4-7-22(30)27-13-23(31)32)17-5-6-18-24-19(12-21(26(17,18)3)36-37(33,34)35)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-29H,4-13H2,1-3H3,(H,27,30)(H,31,32)(H,33,34,35)/t14-,15+,16-,17-,18?,19?,20-,21+,24?,25+,26-/m1/s1

InChI Key

JZLKXIMBAHDSBJ-NLKBZSSJSA-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 glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Fatty acyl
Sulfate-ester
Sulfuric acid monoester
Sulfuric acid ester
Alkyl sulfate
N-acyl-amine
Fatty amide
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	-0.22	ALOGPS
logP	0.031	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-0.24	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.58 m³·mol⁻¹	ChemAxon
Polarizability	57.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0002644

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023038

KNApSAcK ID

Not Available

Chemspider ID

13628380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6730

PubChem Compound

21252319

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
Goto J, Chikai T, Nambara T: Studies on steroids. CCXXVII. Separation and determination of bile acid 7- and 12-sulphates in urine by high-performance liquid chromatography with fluorescence labelling. J Chromatogr. 1987 Mar 20;415(1):45-52. [PubMed:3584362 ]

Showing NP-Card for N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine (NP0086999)

MOL for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

3D MOL for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

3D SDF for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

3D-SDF for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

PDB for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

3D PDB for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

SMILES for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

INCHI for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

Structure for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)

3D Structure for NP0086999 (N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine)