NP-MRD: Showing NP-Card for Chenodeoxycholic acid glycine conjugate (NP0086624)

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Record Information

Version

1.0

Created at

2022-05-11 16:26:23 UTC

Updated at

2022-05-11 16:26:23 UTC

NP-MRD ID

NP0086624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chenodeoxycholic acid glycine conjugate

Description

Chenodeoxycholic acid glycine conjugate, also known as (23R)-hydroxychenodeoxycholylglycine or 12-deoxycholylglycine, 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. Chenodeoxycholic acid glycine conjugate is an extremely weak basic (essentially neutral) compound (based on its pKa). Chenodeoxycholic acid glycine conjugate and glycocholic acid can be biosynthesized from chenodeoxycholoyl-CoA and glycine through the action of the enzyme bile acid-coa:Amino acid N-acyltransferase. It was first documented in 1974 (PMID: 4832755). In humans, chenodeoxycholic acid glycine conjugate is involved in the metabolic disorder called familial hypercholanemia (fhca) (PMID: 19212411) (PMID: 832799) (PMID: 659989) (PMID: 1261008).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Chenodeoxycholic acid glycine conjugate.mol
  Mrv1652305231918572D          

 33 36  0  0  0  0            999 V2000
    3.0902    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.3620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069    3.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    3.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1727   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.1308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0292   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3148   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4393   -0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8559    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    0.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.0683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4859   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -2.3058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7437   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.9558    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  1  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
 21 30  2  0  0  0  0
 12 31  1  6  0  0  0
  6 32  1  6  0  0  0
 10 33  1  1  0  0  0
  2 21  1  0  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
    2.4586   -2.4354    1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.6308    0.3282 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9758   -0.7439    0.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6029   -0.2878   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7699    0.5657   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0791    0.7948    0.7597 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5899    1.1621   -1.4341 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7242    1.9917   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7474    1.2506   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5163    0.0671   -0.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9145    1.8507    0.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -1.0604   -0.4076 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7773   -2.2124   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202   -2.1225   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -0.9652    0.7790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6361   -0.2092    1.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6833   -1.1409    1.6450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8916   -2.2827    0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.5184    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.7828    1.2543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7373    0.9996    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3244    0.6686   -0.1625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5694    0.0322    0.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5247   -0.2453   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0809    0.1145   -1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447    0.9644   -0.0586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8541    2.4169   -0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    0.8248    0.1560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3113    0.7217   -1.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    0.7565   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888   -0.1195    0.1541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1849    0.8221    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -3.1074    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2195    2.3329   -2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4517    2.8805   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7870    1.3443   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -0.6229   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5869   -2.1585   -2.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -3.1997   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275   -2.1736   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919   -3.0793    0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -1.3303    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    0.3847    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.5460    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8173   -2.3335    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0169    2.0641    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  1  0
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  4 40  1  0
  7 41  1  0
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  8 43  1  0
 11 44  1  0
M  END

Chenodeoxycholic acid glycine conjugate.mol
  Mrv1652305231918572D          

 33 36  0  0  0  0            999 V2000
    3.0902    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.3620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069    3.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    3.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1727   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.1308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0292   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3148   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4393   -0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8559    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8663    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8871   -3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 21 30  2  0  0  0  0
 12 31  1  6  0  0  0
  6 32  1  6  0  0  0
 10 33  1  1  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1

> <INCHI_KEY>
GHCZAUBVMUEKKP-AHBZRTSYSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.08210111744595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.608022284

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.791653018199504

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732907141500656

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48930218820632587

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
122.07729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Chenodeoxycholic acid glycine conjugate.mol       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0       5.768   6.295   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.882   4.409   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.370   4.808   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.680   7.384   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.256   6.694   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.922  -5.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.922  -4.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.589  -3.534   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.589  -6.614   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.255  -5.844   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.921  -6.614   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.588  -5.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.588  -4.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.746  -3.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.211  -4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.116  -2.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.211  -1.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.687  -0.054   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.598   1.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.996   2.523   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.484   2.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.193   0.267   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.746  -1.994   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.907  -0.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.588  -1.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.921  -1.994   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.921  -3.534   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.255  -4.304   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.255  -2.764   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.573   1.833   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.746  -6.614   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.256  -6.614   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      -3.255  -7.384   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   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7   28                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   28   33                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
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   30    2                                                  
CONECT   22   18                                                            
CONECT   23   17   14   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   13   28                                                  
CONECT   28   27    8   10   29                                             
CONECT   29   28                                                            
CONECT   30   21                                                            
CONECT   31   12                                                            
CONECT   32    6                                                            
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Chenodeoxycholate glycine conjugate	Generator
Chenodeoxycholic acid glycine conjugic acid	Generator
(23R)-Hydroxychenodeoxycholylglycine	HMDB
12-Deoxycholylglycine	HMDB
12-Desoxycholylglycine	HMDB
3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amide	HMDB
Chenodeoxycholylglycine	HMDB
Glycine chenodeoxycholate	HMDB
Glycochenodeoxycholate	HMDB
Glycochenodeoxycholic acid	HMDB
Glycylchenodeoxycholate	HMDB
Glycylchenodeoxycholic acid	HMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-glycine	HMDB
N-(Carboxymethyl)-3a,7a-dihydroxy-5b-cholan-24-amide	HMDB
Acid, glycochenodeoxycholic	HMDB
Chenodeoxycholate, glycine	HMDB
3alpha,7alpha-Dihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide	HMDB
3α,7α-Dihydroxy-N-(carboxymethyl)-5β-cholan-24-amide	HMDB
Chenodeoxycholic acid glycine conjugate	HMDB
Chenodeoxyglycocholic acid	HMDB
N-[(3alpha,5beta,7alpha)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	HMDB
N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	HMDB

Chemical Formula

C₂₆H₄₃NO₅

Average Mass

449.6233 Da

Monoisotopic Mass

449.31412 Da

IUPAC Name

2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-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@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1

InChI Key

GHCZAUBVMUEKKP-AHBZRTSYSA-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
3-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen 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	2.4	ALOGPS
logP	2.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.08 m³·mol⁻¹	ChemAxon
Polarizability	52.08 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

HMDB0000637

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022157

KNApSAcK ID

Not Available

Chemspider ID

17215984

KEGG Compound ID

C05466

BioCyc ID

Not Available

BiGG ID

45866

Wikipedia Link

Not Available

METLIN ID

5610

PubChem Compound

22833540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [PubMed:4832755 ]

Showing NP-Card for Chenodeoxycholic acid glycine conjugate (NP0086624)

MOL for NP0086624 (Chenodeoxycholic acid glycine conjugate)

3D MOL for NP0086624 (Chenodeoxycholic acid glycine conjugate)

3D SDF for NP0086624 (Chenodeoxycholic acid glycine conjugate)

3D-SDF for NP0086624 (Chenodeoxycholic acid glycine conjugate)

PDB for NP0086624 (Chenodeoxycholic acid glycine conjugate)

3D PDB for NP0086624 (Chenodeoxycholic acid glycine conjugate)

SMILES for NP0086624 (Chenodeoxycholic acid glycine conjugate)

INCHI for NP0086624 (Chenodeoxycholic acid glycine conjugate)

Structure for NP0086624 (Chenodeoxycholic acid glycine conjugate)

3D Structure for NP0086624 (Chenodeoxycholic acid glycine conjugate)