NP-MRD: Showing NP-Card for (4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid (NP0153605)

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Record Information

Version

2.0

Created at

2022-09-02 10:17:37 UTC

Updated at

2022-09-02 10:17:37 UTC

NP-MRD ID

NP0153605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid

Description

Taurochenodesoxycholic acid, also known as chenodeoxycholoyltaurine or taurine chenodeoxycholate, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurochenodesoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Taurochenodesoxycholic acid exists in all living organisms, ranging from bacteria to humans. Taurochenodesoxycholic acid can be biosynthesized from chenodeoxycholoyl-CoA and taurine through its interaction with the enzyme bile acid-coa:Amino acid N-acyltransferase. A bile acid taurine conjugate of chenodeoxycholic acid. (4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid is found in Trypanosoma brucei. (4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid was first documented in 1974 (PMID: 4832755). In humans, taurochenodesoxycholic acid is involved in cerebrotendinous xanthomatosis (ctx) (PMID: 16382575) (PMID: 580732).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309201916022D          

 39 42  0  0  0  0            999 V2000
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 21  1  1  1  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652309201916022D          

 39 42  0  0  0  0            999 V2000
 9998.933710001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7957 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10000.2043 9999.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.719610001.2909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.434010001.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.150010001.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910001.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579810001.2909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.293710001.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.009710001.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.725710001.7035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.138310002.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.313010002.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.441710001.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910002.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.004710001.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.434010000.8782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.719410000.4603    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 11  3  1  6  0  0  0
 20  9  1  0  0  0  0
  9  6  1  6  0  0  0
 12  7  1  1  0  0  0
 15  4  1  6  0  0  0
  9 18  1  0  0  0  0
 18  2  1  1  0  0  0
 17 10  1  0  0  0  0
 17  5  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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  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
 32 33  2  0  0  0  0
 32 34  2  0  0  0  0
 32 35  1  0  0  0  0
 39 25  1  0  0  0  0
 39 38  1  6  0  0  0
 39 21  1  0  0  0  0
 39 24  1  0  0  0  0
 22  8  1  6  0  0  0
 12 22  1  0  0  0  0
 19 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0153605

> <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)NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1

> <INCHI_KEY>
BHTRKEVKTKCXOH-BJLOMENOSA-N

> <FORMULA>
C26H45NO6S

> <MOLECULAR_WEIGHT>
499.704

> <EXACT_MASS>
499.296758867

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.655747046215936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.0968020386753499

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.47697536728532

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.8004715356003853

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3160397423134701

> <JCHEM_POLAR_SURFACE_AREA>
123.92999999999999

> <JCHEM_REFRACTIVITY>
130.67899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.48e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-SEP-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-SEP-19         0                                  
HETATM    1  C   UNK     0    8664.6768668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.6858666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8664.6808662.405   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8656.6878662.405   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8660.6858661.633   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8662.0158663.961   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8663.3468666.266   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8664.6768663.961   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8662.0158665.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0158662.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3488663.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3488664.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3518665.491   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8658.0178664.721   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.0178663.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.3518662.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.6858663.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.6858664.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.3458667.820   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.0118667.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.6788667.050   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8664.6788665.510   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8666.1438665.034   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.0488666.280   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.1438669.076   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.4778669.847   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.8138669.076   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.1468669.847   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8671.4828669.076   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8672.8158669.847   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8674.1518669.076   0.000  0.00  0.00           C+0
HETATM   32  S   UNK     0    8675.4888669.847   0.000  0.00  0.00           S+0
HETATM   33  O   UNK     0    8676.2588671.183   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8674.7188671.183   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8676.8258669.076   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0    8670.1468671.387   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0    8664.8098669.847   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0    8667.4778668.306   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0    8666.1438667.526   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   18                                                            
CONECT    3   11                                                            
CONECT    4   15                                                            
CONECT    5   17                                                            
CONECT    6    9                                                            
CONECT    7   12                                                            
CONECT    8   22                                                            
CONECT    9   12   20    6   18                                             
CONECT   10   11   17                                                       
CONECT   11   10   12    3                                                  
CONECT   12    9   11    7   22                                             
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   10    5                                             
CONECT   18   13   17    9    2                                             
CONECT   19   20   21                                                       
CONECT   20   19    9                                                       
CONECT   21   22   39   19    1                                             
CONECT   22   21   23    8   12                                             
CONECT   23   22   24                                                       
CONECT   24   23   39                                                       
CONECT   25   26   37   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   28                                                            
CONECT   37   25                                                            
CONECT   38   39                                                            
CONECT   39   25   38   21   24                                             
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
Chenodeoxycholoyltaurine	ChEBI
Taurine chenodeoxycholate	ChEBI
Taurochenodeoxycholate	ChEBI
Taurochenodeoxycholic acid	Kegg
Taurine chenodeoxycholic acid	Generator
Taurochenodesoxycholate	Generator
12-Deoxycholyltaurine	HMDB
12-Desoxycholyltaurine	HMDB
3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide	HMDB
Chenodeoxycholyltaurine	HMDB
Chenyltaurine	HMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurine	HMDB
Acid, taurochenodeoxycholic	HMDB
Chenodeoxycholate, taurine	HMDB

Chemical Formula

C₂₆H₄₅NO₆S

Average Mass

499.7040 Da

Monoisotopic Mass

499.29676 Da

IUPAC Name

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

Traditional Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic 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)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1

InChI Key

BHTRKEVKTKCXOH-BJLOMENOSA-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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

Substituents

Taurinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Fatty acyl
Fatty amide
N-acyl-amine
Alkanesulfonic acid
Cyclic alcohol
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid taurine conjugate (CHEBI:16525 )
C26 bile acids, alcohols, and derivatives (C05465 )
Taurine conjugates (C05465 )
Taurine conjugates (LMST05040005 )

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	1.38	ALOGPS
logP	1.1	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-0.8	ChemAxon
pKa (Strongest Basic)	-0.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.68 m³·mol⁻¹	ChemAxon
Polarizability	56.66 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

HMDB0000951

DrugBank ID

DB08833

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022335

KNApSAcK ID

Not Available

Chemspider ID

343282

KEGG Compound ID

C05465

BioCyc ID

CHENODEOXYCHOLOYLTAURINE

BiGG ID

45864

Wikipedia Link

Not Available

METLIN ID

5897

PubChem Compound

387316

PDB ID

Not Available

ChEBI ID

16525

Good Scents ID

Not Available

References

General References

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 ]
Ijare OB, Somashekar BS, Jadegoud Y, Nagana Gowda GA: 1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media. Lipids. 2005 Oct;40(10):1031-41. doi: 10.1007/s11745-005-1466-1. [PubMed:16382575 ]
Schwenk M, Hofmann AF, Carlson GL, Carter JA, Coulston F, Greim H: Bile acid conjugation in the chimpanzee: effective sulfation of lithocholic acid. Arch Toxicol. 1978 Apr 27;40(2):109-18. doi: 10.1007/BF01891965. [PubMed:580732 ]
LOTUS database [Link]

Showing NP-Card for (4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid (NP0153605)

MOL for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

3D MOL for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

3D SDF for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

3D-SDF for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

PDB for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

3D PDB for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

SMILES for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

INCHI for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

Structure for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)

3D Structure for NP0153605 ((4r)-4-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-n-(2-sulfoethyl)pentanimidic acid)