NP-MRD: Showing NP-Card for {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid (NP0289951)

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Record Information

Version

2.0

Created at

2022-09-09 20:23:17 UTC

Updated at

2022-09-09 20:23:17 UTC

NP-MRD ID

NP0289951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid

Description

Sulfolithocholylglycine, also known as glycolithocholate 3-sulfate or sulfoglycolithocholate, 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. Thus, sulfolithocholylglycine is considered to be a steroid conjugate lipid molecule. Sulfolithocholylglycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid is found in Apis cerana. {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid was first documented in 1975 (PMID: 1097294). The 3-O-sulfo derivative of glycolithocholic acid (PMID: 832799) (PMID: 1150035) (PMID: 12231118).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303062020152D          

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M  END

     RDKit          3D

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M  END


  Mrv1652303062020152D          

 40 43  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22  3  1  6  0  0  0
 23 13  1  0  0  0  0
 13  8  1  1  0  0  0
 20 12  1  0  0  0  0
 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
 18  9  1  6  0  0  0
 15 19  1  0  0  0  0
 19 10  1  1  0  0  0
 28 29  1  0  0  0  0
 28 40  1  6  0  0  0
 29 30  1  0  0  0  0
 29 39  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 38  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 19 25  1  0  0  0  0
 25 11  1  6  0  0  0
 16 24  1  0  0  0  0
 24  1  1  1  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289951

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

> <INCHI_KEY>
FHXBAFXQVZOILS-OETIFKLTSA-N

> <FORMULA>
C26H43NO7S

> <MOLECULAR_WEIGHT>
513.69

> <EXACT_MASS>
513.276023903

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.914850737132326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
2.6445759787310394

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.773272809670727

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.0995010181869347

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7149687684002468

> <JCHEM_POLAR_SURFACE_AREA>
130.0

> <JCHEM_REFRACTIVITY>
130.47659999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-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  S   UNK     0    8657.3878663.173   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0    8656.6158664.507   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.1568664.507   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8656.0468662.401   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8662.7168661.633   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8664.0468663.961   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8665.3768666.266   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0    8666.7068663.961   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8662.7148664.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7148663.179   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0478662.409   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3818663.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3778667.816   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.0448667.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.0448665.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.3778664.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.3868665.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.0528664.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8660.0528663.179   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.3868662.409   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.7118667.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.7118665.506   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.1768665.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.0818666.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8668.1768667.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8668.1768669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8669.5128669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8670.8448669.062   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8672.1808669.832   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0    8673.5128669.062   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0    8674.8488669.832   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8676.1808669.062   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0    8677.5168669.832   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0    8676.1808667.522   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0    8672.1808671.372   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0    8666.8428669.832   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0    8669.5128668.292   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2   12                                                            
CONECT    3    4   22                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8   13                                                            
CONECT    9   18                                                            
CONECT   10   19                                                            
CONECT   11   25                                                            
CONECT   12   13   20    2   18                                             
CONECT   13   12   14   23    8                                             
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   17   24                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12    9                                             
CONECT   19   18   15   10   25                                             
CONECT   20   21   12                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23    3                                                  
CONECT   23   22   13                                                       
CONECT   24   25   16    1   28                                             
CONECT   25   24   26   19   11                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   29   40   24   27                                             
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   32                                                            
CONECT   39   29                                                            
CONECT   40   28                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
Glycolithocholate 3-sulfate	ChEBI
Glycolithocholate sulfate	ChEBI
Glycolithocholic acid 3-sulfate	ChEBI
Glycolithocholic acid sulfate	ChEBI
Sulfoglycolithocholate	ChEBI
Glycolithocholate 3-sulphate	Generator
Glycolithocholic acid 3-sulfuric acid	Generator
Glycolithocholic acid 3-sulphuric acid	Generator
Glycolithocholate sulphate	Generator
Glycolithocholic acid sulfuric acid	Generator
Glycolithocholic acid sulphuric acid	Generator
Sulfoglycolithocholic acid	Generator
Sulphoglycolithocholate	Generator
Sulphoglycolithocholic acid	Generator
Sulpholithocholylglycine	Generator
Sulfolithoglycocholine	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-sulphate	HMDB
Glycolithocholic acid 3alpha-sulfate	HMDB
Glycolithocholic acid 3alpha-sulphate	HMDB
Glycolithocholic acid 3α-sulfate	HMDB
Glycolithocholic acid 3α-sulphate	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
Sulfolithocholylglycine	ChEBI

Chemical Formula

C₂₆H₄₃NO₇S

Average Mass

513.6900 Da

Monoisotopic Mass

513.27602 Da

IUPAC Name

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

Traditional Name

[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]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](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

InChI Key

FHXBAFXQVZOILS-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

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
Sulfated steroid skeleton
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Sulfuric acid monoester
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Organic sulfuric acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:9347 )
bile acid glycine conjugate (CHEBI:9347 )

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	1.1	ALOGPS
logP	2.64	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.48 m³·mol⁻¹	ChemAxon
Polarizability	56.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0002639

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023034

KNApSAcK ID

Not Available

Chemspider ID

65188

KEGG Compound ID

C11301

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72222

PDB ID

Not Available

ChEBI ID

9347

Good Scents ID

Not Available

References

General References

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 ]
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 ]
Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. doi: 10.1016/s0039-128x(02)00036-3. [PubMed:12231118 ]
LOTUS database [Link]

Showing NP-Card for {[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid (NP0289951)

MOL for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

3D MOL for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

3D SDF for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

3D-SDF for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

PDB for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

3D PDB for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

SMILES for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

INCHI for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

Structure for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)

3D Structure for NP0289951 ({[(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-1-hydroxypentylidene]amino}acetic acid)