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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:25:02 UTC

Update Date

2022-09-22 18:34:48 UTC

HMDB ID

HMDB0341323

Secondary Accession Numbers

None

Metabolite Identification

Common Name

glyco-beta-muricholic acid

Description

2-{[(4R)-1-hydroxy-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentylidene]amino}acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311042017412D          

 33 36  0  0  1  0            999 V2000
   -3.5635   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8490   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -1.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378   -1.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -2.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780   -1.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3642   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1712   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5837   -0.9280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0316   -1.5411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2866   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0935   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6456   -1.8841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3906   -1.0995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9427   -0.4864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7496   -0.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0046   -1.4426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4525   -2.0556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7075   -2.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5145   -3.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0665   -2.3987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8115   -1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8735   -2.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005   -2.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3017   -0.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6877    0.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4185   -2.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  2  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 15  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  1  0  0  0
 27 29  1  1  0  0  0
 24 30  1  6  0  0  0
 22 31  1  6  0  0  0
 21 32  1  6  0  0  0
 16 33  1  6  0  0  0
M  END


  Mrv1652311042017412D          

 33 36  0  0  1  0            999 V2000
   -3.5635   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8490   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -1.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378   -1.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7233   -2.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780   -1.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3642   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1712   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5837   -0.9280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0316   -1.5411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2866   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0935   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6456   -1.8841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3906   -1.0995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9427   -0.4864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7496   -0.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0046   -1.4426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4525   -2.0556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7075   -2.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5145   -3.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0665   -2.3987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8115   -1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8735   -2.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005   -2.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3017   -0.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6877    0.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4185   -2.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  2  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 15  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  1  0  0  0
 27 29  1  1  0  0  0
 24 30  1  6  0  0  0
 22 31  1  6  0  0  0
 21 32  1  6  0  0  0
 16 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0341323

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO6/c1-14(4-7-20(29)27-13-21(30)31)16-5-6-17-22-18(9-11-25(16,17)2)26(3)10-8-15(28)12-19(26)23(32)24(22)33/h14-19,22-24,28,32-33H,4-13H2,1-3H3,(H,27,29)(H,30,31)/t14-,15-,16-,17+,18+,19+,22+,23+,24-,25-,26-/m1/s1

> <INCHI_KEY>
ZQYUKJFJPJDMMR-IIWZPVADSA-N

> <FORMULA>
C26H43NO6

> <MOLECULAR_WEIGHT>
465.631

> <EXACT_MASS>
465.309038109

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.833855682522156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.6110724069999995

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.620411472878

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732693913013486

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4837474864590656

> <JCHEM_POLAR_SURFACE_AREA>
127.09000000000002

> <JCHEM_REFRACTIVITY>
123.36179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-NOV-20         0                                  
HETATM    1  C   UNK     0      -6.652  -4.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.652  -3.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.318  -2.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.984  -3.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.651  -2.250   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.651  -0.710   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -1.317  -3.020   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.017  -2.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.350  -3.020   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.684  -2.250   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.350  -4.560   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -7.986  -2.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.146  -0.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.653  -0.399   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.423  -1.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.392  -2.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.868  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -11.375  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.405  -3.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.929  -2.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.960  -0.908   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.466  -1.228   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.942  -2.693   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.911  -3.837   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.387  -5.302   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -15.894  -5.622   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.924  -4.478   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -16.448  -3.013   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -18.430  -4.798   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -12.881  -4.982   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -15.496  -0.084   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -12.484   0.557   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -8.248  -3.907   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   12   17   33                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   19   25   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   22                                                            
CONECT   32   21                                                            
CONECT   33   16                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{[(4R)-1-hydroxy-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentylidene]amino}acetate	Generator

Chemical Formula

C₂₆H₄₃NO₆

Average Molecular Weight

465.631

Monoisotopic Molecular Weight

465.309038109

IUPAC Name

2-[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H43NO6/c1-14(4-7-20(29)27-13-21(30)31)16-5-6-17-22-18(9-11-25(16,17)2)26(3)10-8-15(28)12-19(26)23(32)24(22)33/h14-19,22-24,28,32-33H,4-13H2,1-3H3,(H,27,29)(H,30,31)/t14-,15-,16-,17+,18+,19+,22+,23+,24-,25-,26-/m1/s1

InChI Key

ZQYUKJFJPJDMMR-IIWZPVADSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.46	ALOGPS
logP	1.61	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.36 m³·mol⁻¹	ChemAxon
Polarizability	52.83 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68004087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137333454

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for glyco-beta-muricholic acid (HMDB0341323)

MOL for HMDB0341323 (glyco-beta-muricholic acid)

3D MOL for HMDB0341323 (glyco-beta-muricholic acid)

3D SDF for HMDB0341323 (glyco-beta-muricholic acid)

3D-SDF for HMDB0341323 (glyco-beta-muricholic acid)

PDB for HMDB0341323 (glyco-beta-muricholic acid)

3D PDB for HMDB0341323 (glyco-beta-muricholic acid)

SMILES for HMDB0341323 (glyco-beta-muricholic acid)

INCHI for HMDB0341323 (glyco-beta-muricholic acid)

Structure for HMDB0341323 (glyco-beta-muricholic acid)

3D Structure for HMDB0341323 (glyco-beta-muricholic acid)

Predicted Kovats Retention Indices