NP-MRD: Showing NP-Card for Glycoursodeoxycholic acid (NP0086635)

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Record Information

Version

1.0

Created at

2022-05-11 16:26:42 UTC

Updated at

2022-05-11 16:26:42 UTC

NP-MRD ID

NP0086635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycoursodeoxycholic acid

Description

Glycoursodeoxycholic acid, also known as GUDCA or ursodeoxycholylglycine, 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. Glycoursodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. It was first documented in 2015 (PMID: 24848512). Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol (PMID: 26009005) (PMID: 26382575) (PMID: 26639449) (PMID: 27322559).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302052016282D          

 37 40  0  0  0  0            999 V2000
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 9997.3557 9998.5732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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 13 21  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652302052016282D          

 37 40  0  0  0  0            999 V2000
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 20  3  1  1  0  0  0
 12 18  1  0  0  0  0
 18  5  1  1  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 36  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 35  2  0  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 34  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[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/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-XROMFQGDSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.19389243425874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,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-[(1S,2S,5R,7S,9S,10R,11S,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                                 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    8663.0618666.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.0718664.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8663.0658660.143   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8655.0778660.143   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8659.0718659.371   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8660.4018661.699   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8661.7318664.003   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8663.0618661.699   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8657.7418663.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8656.4078662.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8656.4078660.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8657.7418660.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.7328665.554   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.3988664.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.3988663.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.7328662.474   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.0688662.457   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8659.0688660.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8660.4028660.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.7358660.917   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.0658664.784   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.0658663.244   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.5308662.768   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.4358664.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8664.5308665.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8664.5308666.800   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8665.8648667.570   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.2008666.800   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8668.5328667.570   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8669.8688666.800   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0    8671.2008667.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8672.5368666.800   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0    8673.8688667.570   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8672.5368665.260   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8668.5328669.110   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0    8663.1968667.570   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0    8665.8648666.030   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   17                                                            
CONECT    3   20                                                            
CONECT    4   11                                                            
CONECT    5   18                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   22                                                            
CONECT    9   10   17                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   18                                                       
CONECT   13   14   21                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17    6                                             
CONECT   16   15   20    7   22                                             
CONECT   17   18    9    2   15                                             
CONECT   18   17   19   12    5                                             
CONECT   19   18   20                                                       
CONECT   20   19    3   16                                                  
CONECT   21   22   25   13    1                                             
CONECT   22   21   23   16    8                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   37   21   24                                             
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29                                                            
CONECT   36   26                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
3alpha,7beta-Dihydroxy-5beta-cholanoylglycine	ChEBI
Glycine ursodeoxycholic acid	ChEBI
Glycylursodeoxycholic acid	ChEBI
GUDCA	ChEBI
N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)glycine	ChEBI
N-[(3alpha,5beta,7beta)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	ChEBI
Ursodeoxycholylglycine	ChEBI
3a,7b-Dihydroxy-5b-cholanoylglycine	Generator
3Α,7β-dihydroxy-5β-cholanoylglycine	Generator
Glycine ursodeoxycholate	Generator
Glycylursodeoxycholate	Generator
N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycine	Generator
N-(3Α,7β-dihydroxy-5β-cholan-24-oyl)glycine	Generator
N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	Generator
N-[(3Α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl]glycine	Generator
Glycoursodeoxycholate	Generator
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-oic acid	HMDB
(3β,5β,7β)-3,7-Dihydroxycholan-24-oic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholan-24-oic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholanic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholanoic acid	HMDB
3beta-Ursodeoxycholic acid	HMDB
3β,7β-Dihydroxy-5β-cholan-24-oic acid	HMDB
3β,7β-Dihydroxy-5β-cholanic acid	HMDB
3β,7β-Dihydroxy-5β-cholanoic acid	HMDB
3β-Ursodeoxycholic acid	HMDB
Isoursodeoxycholic acid	HMDB

Chemical Formula

C₂₆H₄₃NO₅

Average Mass

449.6233 Da

Monoisotopic Mass

449.31412 Da

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,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-[(1S,2S,5R,7S,9S,10R,11S,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@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[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/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-XROMFQGDSA-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
7-alpha-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

C24 bile acids, alcohols, and derivatives (LMST04010445 )

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	52.19 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

HMDB0000708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022194

KNApSAcK ID

Not Available

Chemspider ID

19973534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5676

PubChem Compound

12310288

PDB ID

Not Available

ChEBI ID

89929

Good Scents ID

Not Available

References

General References

Vaz AR, Cunha C, Gomes C, Schmucki N, Barbosa M, Brites D: Glycoursodeoxycholic acid reduces matrix metalloproteinase-9 and caspase-9 activation in a cellular model of superoxide dismutase-1 neurodegeneration. Mol Neurobiol. 2015;51(3):864-77. doi: 10.1007/s12035-014-8731-8. Epub 2014 May 22. [PubMed:24848512 ]
Mayengbam S, House JD, Aliani M: Investigation of vitamin B(6) inadequacy, induced by exposure to the anti-B(6) factor 1-amino D-proline, on plasma lipophilic metabolites of rats: a metabolomics approach. Eur J Nutr. 2016 Apr;55(3):1213-23. doi: 10.1007/s00394-015-0934-x. Epub 2015 May 26. [PubMed:26009005 ]
Hu M, Fok BS, Wo SK, Lee VH, Zuo Z, Tomlinson B: Effect of common polymorphisms of the farnesoid X receptor and bile acid transporters on the pharmacokinetics of ursodeoxycholic acid. Clin Exp Pharmacol Physiol. 2016 Jan;43(1):34-40. doi: 10.1111/1440-1681.12490. [PubMed:26382575 ]
Singh N, Bhattacharyya D: Identification of the anti-oxidant components in a two-step solvent extract of bovine bile lipid: Application of reverse phase HPLC, mass spectrometry and fluorimetric assays. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Apr 15;1019:83-94. doi: 10.1016/j.jchromb.2015.11.020. Epub 2015 Nov 30. [PubMed:26639449 ]
Semba RD, Gonzalez-Freire M, Moaddel R, Trehan I, Maleta KM, Khadeer M, Ordiz MI, Ferrucci L, Manary MJ: Environmental Enteric Dysfunction Is Associated With Altered Bile Acid Metabolism. J Pediatr Gastroenterol Nutr. 2017 Apr;64(4):536-540. doi: 10.1097/MPG.0000000000001313. [PubMed:27322559 ]

Showing NP-Card for Glycoursodeoxycholic acid (NP0086635)

MOL for NP0086635 (Glycoursodeoxycholic acid)

3D MOL for NP0086635 (Glycoursodeoxycholic acid)

3D SDF for NP0086635 (Glycoursodeoxycholic acid)

3D-SDF for NP0086635 (Glycoursodeoxycholic acid)

PDB for NP0086635 (Glycoursodeoxycholic acid)

3D PDB for NP0086635 (Glycoursodeoxycholic acid)

SMILES for NP0086635 (Glycoursodeoxycholic acid)

INCHI for NP0086635 (Glycoursodeoxycholic acid)

Structure for NP0086635 (Glycoursodeoxycholic acid)

3D Structure for NP0086635 (Glycoursodeoxycholic acid)