NP-MRD: Showing NP-Card for Lithocholyltaurine (NP0086638)

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Record Information

Version

2.0

Created at

2022-05-11 16:26:47 UTC

Updated at

2022-05-11 16:26:47 UTC

NP-MRD ID

NP0086638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lithocholyltaurine

Description

Lithocholyltaurine, also known as taurolithocholate, 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. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Lithocholyltaurine is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, lithocholyltaurine is involved in the metabolic disorder called familial hypercholanemia (fhca). Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine was first documented in 2005 (PMID: 15763547). One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1) (PMID: 16981261) (PMID: 16332456).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305231919422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305231919422D          

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 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 14 15  1  0  0  0  0
 15 33  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  1  0  0  0  0
 18 25  1  0  0  0  0
 19 28  1  6  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 26  1  0  0  0  0
 22 26  1  0  0  0  0
 23 25  1  0  0  0  0
 24 29  2  0  0  0  0
 24 27  1  0  0  0  0
 30 33  1  0  0  0  0
 31 33  2  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18?,19-,20?,21?,22?,23?,25+,26-/m1/s1

> <INCHI_KEY>
QBYUNVOYXHFVKC-LVMSMGIASA-N

> <FORMULA>
C26H45NO5S

> <MOLECULAR_WEIGHT>
483.704

> <EXACT_MASS>
483.301844245

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.72793921602326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.4811742052517807

> <ALOGPS_LOGS>
-6.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.60199909179077

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.6276888737017137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1127164403915377

> <JCHEM_POLAR_SURFACE_AREA>
103.69999999999999

> <JCHEM_REFRACTIVITY>
129.08649999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      11.413 -10.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.766 -15.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.234 -11.921   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.079 -10.323   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.117 -18.631   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.184 -17.521   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.886 -13.534   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.363 -14.982   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.387 -11.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.632 -17.524   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.833 -14.193   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.699 -16.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.901 -13.083   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.411 -10.497   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.719 -11.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.555 -19.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.721 -11.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.622 -18.262   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.060 -19.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.756 -16.042   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.671 -12.588   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.824 -14.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.261 -15.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.745 -10.410   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.194 -16.783   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.396 -13.452   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      18.053 -11.223   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       4.992 -20.114   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.795  -8.871   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      21.351  -9.226   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      22.803 -11.942   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      23.435  -9.858   0.000  0.00  0.00           O+0
HETATM   33  S   UNK     0      22.077 -10.584   0.000  0.00  0.00           S+0
CONECT    1   17                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   17    9                                                       
CONECT    5    6   18                                                       
CONECT    6    5   20                                                       
CONECT    7   21    8                                                       
CONECT    8    7   22                                                       
CONECT    9    4   24                                                       
CONECT   10   19   12                                                       
CONECT   11   23   13                                                       
CONECT   12   10   25                                                       
CONECT   13   11   26                                                       
CONECT   14   27   15                                                       
CONECT   15   14   33                                                       
CONECT   16   18   19                                                       
CONECT   17    1    4   21                                                  
CONECT   18    5   16   25                                                  
CONECT   19   10   16   28                                                  
CONECT   20    6   22   23                                                  
CONECT   21    7   17   26                                                  
CONECT   22    8   20   26                                                  
CONECT   23   11   20   25                                                  
CONECT   24    9   29   27                                                  
CONECT   25    2   12   18   23                                             
CONECT   26    3   13   21   22                                             
CONECT   27   14   24                                                       
CONECT   28   19                                                            
CONECT   29   24                                                            
CONECT   30   33                                                            
CONECT   31   33                                                            
CONECT   32   33                                                            
CONECT   33   15   30   31   32                                             
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-[(3alpha-Hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid	HMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonate	HMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic acid	HMDB
3a-Hydroxy-5b-cholanoyltaurine	HMDB
3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide	HMDB
Cholane ethanesulfonic acid deriv.	HMDB
Lithocholic acid taurine conjugate	HMDB
Lithocholic acid taurine conjugic acid	HMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-taurine	HMDB
Taurolithocholate	HMDB
Taurolithocholic acid	HMDB
Lithocholate, taurine	HMDB
Taurine lithocholate	HMDB
Taurolithocholic acid, monosodium salt	HMDB
Acid, taurolithocholic	HMDB

Chemical Formula

C₂₆H₄₅NO₅S

Average Mass

483.7040 Da

Monoisotopic Mass

483.30184 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18?,19-,20?,21?,22?,23?,25+,26-/m1/s1

InChI Key

QBYUNVOYXHFVKC-LVMSMGIASA-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 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
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Fatty amide
N-acyl-amine
Fatty acyl
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Alkanesulfonic acid
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organosulfur compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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	2.1	ALOGPS
logP	2.48	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	-0.63	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.09 m³·mol⁻¹	ChemAxon
Polarizability	55.73 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

HMDB0000722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022203

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02592

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taurolithocholic acid

METLIN ID

5690

PubChem Compound

53477716

PDB ID

Not Available

ChEBI ID

36259

Good Scents ID

Not Available

References

General References

Watanabe N, Kagawa T, Kojima S, Takashimizu S, Nagata N, Nishizaki Y, Mine T: Taurolithocholate impairs bile canalicular motility and canalicular bile secretion in isolated rat hepatocyte couplets. World J Gastroenterol. 2006 Sep 7;12(33):5320-5. doi: 10.3748/wjg.v12.i33.5320. [PubMed:16981261 ]
Crocenzi FA, Basiglio CL, Perez LM, Portesio MS, Pozzi EJ, Roma MG: Silibinin prevents cholestasis-associated retrieval of the bile salt export pump, Bsep, in isolated rat hepatocyte couplets: possible involvement of cAMP. Biochem Pharmacol. 2005 Apr 1;69(7):1113-20. doi: 10.1016/j.bcp.2005.01.009. [PubMed:15763547 ]
Hayashi H, Takada T, Suzuki H, Onuki R, Hofmann AF, Sugiyama Y: Transport by vesicles of glycine- and taurine-conjugated bile salts and taurolithocholate 3-sulfate: a comparison of human BSEP with rat Bsep. Biochim Biophys Acta. 2005 Dec 30;1738(1-3):54-62. doi: 10.1016/j.bbalip.2005.10.006. Epub 2005 Nov 15. [PubMed:16332456 ]

Showing NP-Card for Lithocholyltaurine (NP0086638)

MOL for NP0086638 (Lithocholyltaurine)

3D MOL for NP0086638 (Lithocholyltaurine)

3D SDF for NP0086638 (Lithocholyltaurine)

3D-SDF for NP0086638 (Lithocholyltaurine)

PDB for NP0086638 (Lithocholyltaurine)

3D PDB for NP0086638 (Lithocholyltaurine)

SMILES for NP0086638 (Lithocholyltaurine)

INCHI for NP0086638 (Lithocholyltaurine)

Structure for NP0086638 (Lithocholyltaurine)

3D Structure for NP0086638 (Lithocholyltaurine)