NP-MRD: Showing NP-Card for Taurolithocholic acid 3-sulfate (NP0086991)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:36:42 UTC

Updated at

2022-05-11 16:36:42 UTC

NP-MRD ID

NP0086991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taurolithocholic acid 3-sulfate

Description

Taurolithocholic acid 3-sulfate, also known as 3alpha-sulfatolithocholyltaurine or SLCT-3-sulfate, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurolithocholic acid 3-sulfate was first documented in 1993 (PMID: 8437507). Taurolithocholic acid 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16332456) (PMID: 10103175) (PMID: 12523936) (PMID: 24177139).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310181922572D          

 42 45  0  0  0  0            999 V2000
 9999.649410001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3695 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6549 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2432 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0686 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9382 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2240 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6494 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7975 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7975 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5097 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5097 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2242 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9387 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.937110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2226 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9371 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.651610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6516 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4362 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9211 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.436210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.436210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.149910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.008510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.439910001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.852410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.027410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.155510001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.721210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14  3  1  6  0  0  0
 15 17  1  0  0  0  0
 17  8  1  1  0  0  0
 12 16  1  0  0  0  0
 16  2  1  1  0  0  0
 22 16  1  0  0  0  0
 22  9  1  6  0  0  0
 19 23  1  0  0  0  0
 23 10  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 28 42  1  6  0  0  0
 29 30  1  0  0  0  0
 29 41  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 40  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  2  0  0  0  0
 36 39  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 23 25  1  0  0  0  0
 25 11  1  6  0  0  0
 20 24  1  0  0  0  0
 24  1  1  1  0  0  0
M  END

     RDKit          3D

 82 85  0  0  0  0  0  0  0  0999 V2000
   -2.9971   -0.9437   -2.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170   -2.0110   -1.7951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9421   -2.7201   -1.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9035   -2.1292   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6705   -0.9415   -0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515   -0.3353   -1.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5524   -0.3421    0.2242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3351    0.8347   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4824    2.0400   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3701    2.4286    0.9792 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.4870    1.2633    1.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1948    2.8357    2.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693    3.7691    0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148   -1.5836   -0.6952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5362   -2.7388    0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -2.3394    0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450   -1.0333    0.4228 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6138   -0.8565    0.2516 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431   -1.1062    1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -0.1151    1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0609    0.0556    0.5131 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4266    0.6235    0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    1.8979    1.4801 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2106    1.5258    2.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6008    1.8515    3.6991 S   0  0  1  0  0  6  0  0  0  0  0  0
    7.3710    2.9635    3.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2316    2.2354    5.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5928    0.5006    3.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705    2.8261    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4422    2.4198   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.9747   -0.3580 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6482    0.6312   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028    0.5839   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0082    0.8819   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    0.3749   -1.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -1.0710   -0.9938 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3228   -1.9791   -1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755    0.0520   -2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798   -1.2162   -3.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485   -0.9087   -3.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1600   -2.8265   -2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -3.7721   -1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039   -2.9566   -2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535   -2.9211   -0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.9287    0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6110   -0.8001    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9434    1.0915    0.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9713    0.6268   -0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1798    2.8971   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9292    1.9524   -1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3581    3.8795   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -0.8118   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070   -2.8963    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -3.6651   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4559   -2.1943    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327   -3.0988    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357   -0.1604    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0100   -1.5152   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7122   -2.1126    1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5030   -1.0366    2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    0.8151    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007   -0.5148    2.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1788   -0.9090   -0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -0.1001    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    0.7300   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556    2.3599    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5214    0.7652    3.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343    3.0691    1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7546    3.8196    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4240    2.8993    0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    2.8850   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158    1.4312   -2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.6436   -1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -0.3792   -2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914    1.2069    0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    2.0106   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063    0.5226   -2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533    0.4695   -2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    0.9333   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370   -2.4299   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6906   -2.8525   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010   -1.4860   -2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  6
 23 24  1  0
 25 24  1  6
 25 28  1  0
 25 26  2  0
 25 27  2  0
 14  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 10  1  0
 10 13  1  6
 10 11  2  0
 10 12  2  0
 36 14  1  0
 36 17  1  0
 33 18  1  0
 31 21  1  0
 14 52  1  1
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  6
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  6
 22 64  1  0
 22 65  1  0
 23 66  1  1
 29 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 32 72  1  0
 32 73  1  0
 32 74  1  0
 33 75  1  1
 34 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
 28 67  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
  9 49  1  0
  9 50  1  0
 13 51  1  0
M  END


  Mrv1652310181922572D          

 42 45  0  0  0  0            999 V2000
 9999.649410001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3695 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6549 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2432 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0686 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9382 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2240 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6494 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7975 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7975 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5097 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5097 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2242 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9387 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.937110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2226 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9371 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.651610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6516 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4362 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9211 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.436210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.436210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.149910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.008510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.439910001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.852410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.027410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.155510001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.721210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14  3  1  6  0  0  0
 15 17  1  0  0  0  0
 17  8  1  1  0  0  0
 12 16  1  0  0  0  0
 16  2  1  1  0  0  0
 22 16  1  0  0  0  0
 22  9  1  6  0  0  0
 19 23  1  0  0  0  0
 23 10  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 28 42  1  6  0  0  0
 29 30  1  0  0  0  0
 29 41  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 40  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  2  0  0  0  0
 36 39  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 23 25  1  0  0  0  0
 25 11  1  6  0  0  0
 20 24  1  0  0  0  0
 24  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086991

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

> <INCHI_KEY>
HSNPMXROZIQAQD-GBURMNQMSA-N

> <FORMULA>
C26H45NO8S2

> <MOLECULAR_WEIGHT>
563.767

> <EXACT_MASS>
563.258658801

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
61.46919818999537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
1.2383031872909969

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-0.6226732220547602

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.613557186637399

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1053721686589895

> <JCHEM_POLAR_SURFACE_AREA>
147.07

> <JCHEM_REFRACTIVITY>
139.07829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-19         0                                  
HETATM    1  C   UNK     0    8666.0128668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.0218666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0238662.405   0.000  0.00  0.00           O+0
HETATM    4  S   UNK     0    8656.6898663.173   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0    8655.9218664.507   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8657.4618664.507   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8655.3518662.401   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8662.0218661.633   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8663.3518663.961   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8664.6828666.266   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0    8666.0128663.961   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8660.6898665.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3558664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.3558663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.6898662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.0188664.719   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0188663.179   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3528662.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6868663.179   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6838667.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.3498667.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.3498665.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.6838664.736   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.0168667.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.0168665.506   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.4818665.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.3868666.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.4818667.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8667.4818669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8668.8138669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8670.1498669.062   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8671.4818669.832   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0    8672.8178669.062   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0    8674.1498669.832   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8675.4858669.062   0.000  0.00  0.00           C+0
HETATM   36  S   UNK     0    8676.8218669.832   0.000  0.00  0.00           S+0
HETATM   37  O   UNK     0    8677.5918671.168   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0    8676.0518671.168   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0    8678.1578669.062   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0    8671.4818671.372   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0    8666.1468669.832   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0    8668.8138668.292   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2   16                                                            
CONECT    3    4   14                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8   17                                                            
CONECT    9   22                                                            
CONECT   10   23                                                            
CONECT   11   25                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    3                                                  
CONECT   15   14   17                                                       
CONECT   16   17   12    2   22                                             
CONECT   17   16   18   15    8                                             
CONECT   18   17   19                                                       
CONECT   19   18   23                                                       
CONECT   20   21   24                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   16    9                                             
CONECT   23   22   19   10   25                                             
CONECT   24   25   28   20    1                                             
CONECT   25   24   26   23   11                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   29   42   24   27                                             
CONECT   29   28   30   41                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
CONECT   40   32                                                            
CONECT   41   29                                                            
CONECT   42   28                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonate	ChEBI
3alpha-Sulfatolithocholyltaurine	ChEBI
SLCT-3-Sulfate	ChEBI
Taurolithocholate 3-sulfate	ChEBI
Taurolithocholate sulfate	ChEBI
TLC-S	ChEBI
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonate	Generator
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonate	Generator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
3a-Sulfatolithocholyltaurine	Generator
3a-Sulphatolithocholyltaurine	Generator
3alpha-Sulphatolithocholyltaurine	Generator
3Α-sulfatolithocholyltaurine	Generator
3Α-sulphatolithocholyltaurine	Generator
SLCT-3-Sulfuric acid	Generator
SLCT-3-Sulphate	Generator
SLCT-3-Sulphuric acid	Generator
Taurolithocholate 3-sulphate	Generator
Taurolithocholic acid 3-sulfuric acid	Generator
Taurolithocholic acid 3-sulphuric acid	Generator
Taurolithocholate sulphate	Generator
Taurolithocholic acid sulfuric acid	Generator
Taurolithocholic acid sulphuric acid	Generator
Taurolithocholic acid 3-sulphate	HMDB
Taurolithocholic acid sulfate	HMDB
Taurolithocholic acid sulphate	HMDB
Taurolithocholic acid 3-sulfate	ChEBI

Chemical Formula

C₂₆H₄₅NO₈S₂

Average Mass

563.7670 Da

Monoisotopic Mass

563.25866 Da

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

Traditional Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

InChI Key

HSNPMXROZIQAQD-GBURMNQMSA-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 taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

Substituents

Taurinated bile acid
Sulfated steroid skeleton
Fatty amide
N-acyl-amine
Sulfuric acid monoester
Sulfate-ester
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:17864 )
sulfates (C03642 )
C26 bile acids, alcohols, and derivatives (C03642 )
Taurine conjugates (C03642 )
Sulfates (LMST05020003 )

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	-0.12	ALOGPS
logP	1.24	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.08 m³·mol⁻¹	ChemAxon
Polarizability	61.47 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

HMDB0002580

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023028

KNApSAcK ID

Not Available

Chemspider ID

389078

KEGG Compound ID

C03642

BioCyc ID

TAUROLITHOCHOLATE-SULFATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6716

PubChem Compound

440071

PDB ID

Not Available

ChEBI ID

17864

Good Scents ID

Not Available

References

General References

Hayashi H, Takada T, Suzuki H, Onuki R, Hofmann AF, Sugiyama Y: Transport by vesicles of glycine- and taurine-conjugated bile salts and taurolithocholate 3-sulfate: a comparison of human BSEP with rat Bsep. Biochim Biophys Acta. 2005 Dec 30;1738(1-3):54-62. doi: 10.1016/j.bbalip.2005.10.006. Epub 2005 Nov 15. [PubMed:16332456 ]
Herold BC, Kirkpatrick R, Marcellino D, Travelstead A, Pilipenko V, Krasa H, Bremer J, Dong LJ, Cooper MD: Bile salts: natural detergents for the prevention of sexually transmitted diseases. Antimicrob Agents Chemother. 1999 Apr;43(4):745-51. doi: 10.1128/AAC.43.4.745. [PubMed:10103175 ]
Zelcer N, Reid G, Wielinga P, Kuil A, van der Heijden I, Schuetz JD, Borst P: Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4). Biochem J. 2003 Apr 15;371(Pt 2):361-7. doi: 10.1042/BJ20021886. [PubMed:12523936 ]
Carvalho AC, Sousa RB, Franco AX, Costa JV, Neves LM, Ribeiro RA, Sutton R, Criddle DN, Soares PM, de Souza MH: Protective effects of fucoidan, a P- and L-selectin inhibitor, in murine acute pancreatitis. Pancreas. 2014 Jan;43(1):82-7. doi: 10.1097/MPA.0b013e3182a63b9d. [PubMed:24177139 ]
Adachi Y, Kobayashi H, Shouji M, Kitano M, Okuyama Y, Yamamoto T: Functional integrity of hepatocyte canalicular membrane transport of taurocholate and bilirubin diglucuronide in Eisai hyperbilirubinuria rats. Life Sci. 1993;52(9):777-84. doi: 10.1016/0024-3205(93)90075-e. [PubMed:8437507 ]

Showing NP-Card for Taurolithocholic acid 3-sulfate (NP0086991)

MOL for NP0086991 (Taurolithocholic acid 3-sulfate)

3D MOL for NP0086991 (Taurolithocholic acid 3-sulfate)

3D SDF for NP0086991 (Taurolithocholic acid 3-sulfate)

3D-SDF for NP0086991 (Taurolithocholic acid 3-sulfate)

PDB for NP0086991 (Taurolithocholic acid 3-sulfate)

3D PDB for NP0086991 (Taurolithocholic acid 3-sulfate)

SMILES for NP0086991 (Taurolithocholic acid 3-sulfate)

INCHI for NP0086991 (Taurolithocholic acid 3-sulfate)

Structure for NP0086991 (Taurolithocholic acid 3-sulfate)

3D Structure for NP0086991 (Taurolithocholic acid 3-sulfate)