NP-MRD: Showing NP-Card for Lithocholic acid glycine conjugate (NP0086634)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...Show more...

Record Information

Version

2.0

Created at

2022-05-11 16:26:40 UTC

Updated at

2022-05-11 16:26:40 UTC

NP-MRD ID

NP0086634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lithocholic acid glycine conjugate

Description

Lithocholic acid glycine conjugate, also known as glycolithocholic acid or lithocholylglycine, 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. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. Lithocholic acid glycine conjugate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Is an acyl glycine and a bile acid-glycine conjugate. In humans, lithocholic acid glycine conjugate is involved in the metabolic disorder called familial hypercholanemia (fhca). 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 ). Lithocholic acid glycine conjugate was first documented in 1975 (PMID: 1097294). Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol (PMID: 1150035) (PMID: 1150037).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652302052018532D          

 36 39  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  4  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  6  1  1  0  0  0
 24 25  1  0  0  0  0
 24 36  1  6  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 34  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 15 21  1  0  0  0  0
 21  7  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
M  END

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
    3.9047   -1.5701    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -0.5857   -0.3200 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2405    0.8088   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5018    1.1113   -1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663    0.6524   -0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9078    0.3739    0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074    0.5015   -1.3213 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1891    0.0485   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6530    0.9963    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9854    1.9895    0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8738    0.7416    0.8227 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020   -0.9572    0.3927 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6830   -0.9730    1.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2130   -0.9017    2.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5495   -1.0261    1.0840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9557   -0.6135    1.0851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7833   -1.8168    1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479   -1.8190    0.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086   -0.4412    0.7227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0357   -0.6427    0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6427    0.6345   -0.4508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8443    0.3206   -1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7424    1.2744   -1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3919    0.5751   -1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8156    0.4189   -0.1186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6845    1.8102    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943   -0.2881   -0.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5593    0.4284   -1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238   -0.2864   -1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3634   -0.1944    0.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3330    1.1956    0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1424   -1.4766    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4627   -2.6304   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -1.5859   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132   -0.8411   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607    1.4608   -0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201    1.2259    0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    0.7664   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    2.2452   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8347    0.7227   -2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0223   -0.9398   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9069   -0.0933   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5230    1.5042    0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772   -2.0310    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367   -1.9294    2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753   -0.1641    2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -1.7314    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006    0.0877    2.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -2.0988    0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1473    0.1641    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2543   -2.7386    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799   -1.8461    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2380   -2.4171    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370   -2.3011    1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9606    0.0516    1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7363   -1.1631    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8888   -1.3703   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8943    1.2637    0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9399    0.8607   -1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5381    2.3182   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1510    1.3038   -2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -0.3627   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    1.3234   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    2.5319   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    1.9253    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920    2.1590    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -1.2707   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9665    0.3017   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774    1.5071   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4653   -1.3673   -1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319    0.0838   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1477    1.4113    1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    1.9961   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071    1.3787    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 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
 30 12  1  0
 30 15  1  0
 27 16  1  0
 25 19  1  0
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  1
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  1
 20 56  1  0
 20 57  1  0
 21 58  1  1
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  6
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
  2 35  1  6
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
M  END

  Mrv1652302052018532D          

 36 39  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  4  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  6  1  1  0  0  0
 24 25  1  0  0  0  0
 24 36  1  6  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 34  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 15 21  1  0  0  0  0
 21  7  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086634

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

> <INCHI_KEY>
XBSQTYHEGZTYJE-OETIFKLTSA-N

> <FORMULA>
C26H43NO4

> <MOLECULAR_WEIGHT>
433.6239

> <EXACT_MASS>
433.319208869

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31536464563915

> <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)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.9167870809999994

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.94682470220906

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732726092807374

> <JCHEM_PKA_STRONGEST_BASIC>
-1.114714379730807

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
120.48479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-FEB-20         0                                  
HETATM    1  C   UNK     0    8666.7068668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.7168666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.7218662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.7168661.633   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.0468663.961   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8665.3768666.266   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.7068663.961   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8662.7148664.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7148663.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0478662.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3818663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3778667.816   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0448667.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0448665.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3778664.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.3868665.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.0528664.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.0528663.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.3868662.409   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.7118667.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.7118665.506   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.1768665.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8669.0818666.276   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.1768667.522   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.1768669.062   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.5128669.832   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.8448669.062   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.1808669.832   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8673.5128669.062   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8674.8488669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8676.1808669.062   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8677.5168669.832   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0    8676.1808667.522   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8672.1808671.372   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0    8666.8428669.832   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0    8669.5128668.292   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2    8                                                            
CONECT    3   18                                                            
CONECT    4    9                                                            
CONECT    5   14                                                            
CONECT    6   15                                                            
CONECT    7   21                                                            
CONECT    8    9   16    2   14                                             
CONECT    9    8   10   19    4                                             
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13   20                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    8    5                                             
CONECT   15   14   11    6   21                                             
CONECT   16   17    8                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    3                                                  
CONECT   19   18    9                                                       
CONECT   20   21   12    1   24                                             
CONECT   21   20   22   15    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   36   20   23                                             
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28                                                            
CONECT   35   25                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Glycolithocholate	ChEBI
Lithocholylglycine	ChEBI
N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycine	ChEBI
Glycolithocholic acid	Kegg
N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycine	Generator
N-((3-Α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycine	Generator
Lithocholate glycine conjugate	Generator
Lithocholic acid glycine conjugic acid	Generator
3a-Hydroxy-5b-cholanic acid glycine ester	HMDB
3a-Hydroxy-5b-cholanoylglycine	HMDB
3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oate	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acid	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acid N-(carboxymethyl)amide	HMDB
Lithocholoyglycine	HMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-glycine	HMDB
N-(3a-Hydroxy-5b-cholanoyl)glycine	HMDB
N-(Carboxymethyl)-3a-hydroxy-5b-cholan-24-amide	HMDB
Glycolithocholic acid, monosodium salt	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate	HMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulfate	HMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulphate	HMDB
Glycolithocholic acid 3-sulfate	HMDB
Glycolithocholic acid 3-sulphate	HMDB
Glycolithocholic acid 3alpha-sulfate	HMDB
Glycolithocholic acid 3alpha-sulphate	HMDB
Glycolithocholic acid 3α-sulfate	HMDB
Glycolithocholic acid 3α-sulphate	HMDB
Glycolithocholic acid sulfate	HMDB
Glycolithocholic acid sulphate	HMDB
N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine	HMDB
N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine	HMDB
Sulfoglycolithocholic acid	HMDB
Sulfolithocholylglycine	HMDB

Chemical Formula

C₂₆H₄₃NO₄

Average Mass

433.6239 Da

Monoisotopic Mass

433.31921 Da

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

InChI Key

XBSQTYHEGZTYJE-OETIFKLTSA-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
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

N-acylglycine (CHEBI:37998 )
bile acid glycine conjugate (CHEBI:37998 )
Glycine conjugates (LMST05030009 )

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	3.71	ALOGPS
logP	3.92	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.48 m³·mol⁻¹	ChemAxon
Polarizability	51.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000698

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022187

KNApSAcK ID

Not Available

Chemspider ID

103116

KEGG Compound ID

C15557

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5666

PubChem Compound

115245

PDB ID

Not Available

ChEBI ID

37998

Good Scents ID

Not Available

References

General References

Cowen AE, Korman MG, Hofmann AF, Cass OW, Coffin SB: Metabolism of lithocholate in healthy man. II. Enterohepatic circulation. Gastroenterology. 1975 Jul;69(1):67-76. [PubMed:1097294 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW: Metabolism of lethocholate in healthy man. I. Biotransformation and biliary excretion of intravenously administered lithocholate, lithocholylglycine, and their sulfates. Gastroenterology. 1975 Jul;69(1):59-66. [PubMed:1150035 ]
Cowen AE, Korman MG, Hofmann AF, Thomas PJ: Metabolism of lithocholate in healthy man. III. Plasma disappearance of radioactivity after intravenous injection of labeled lithocholate and its derivatives. Gastroenterology. 1975 Jul;69(1):77-82. [PubMed:1150037 ]

Showing NP-Card for Lithocholic acid glycine conjugate (NP0086634)

MOL for NP0086634 (Lithocholic acid glycine conjugate)

3D MOL for NP0086634 (Lithocholic acid glycine conjugate)

3D SDF for NP0086634 (Lithocholic acid glycine conjugate)

3D-SDF for NP0086634 (Lithocholic acid glycine conjugate)

PDB for NP0086634 (Lithocholic acid glycine conjugate)

3D PDB for NP0086634 (Lithocholic acid glycine conjugate)

SMILES for NP0086634 (Lithocholic acid glycine conjugate)

INCHI for NP0086634 (Lithocholic acid glycine conjugate)

Structure for NP0086634 (Lithocholic acid glycine conjugate)

3D Structure for NP0086634 (Lithocholic acid glycine conjugate)