NP-MRD: Showing NP-Card for Chenodeoxycholic acid 3-sulfate (NP0086993)

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Record Information

Version

2.0

Created at

2022-05-11 16:36:45 UTC

Updated at

2022-05-11 16:36:45 UTC

NP-MRD ID

NP0086993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chenodeoxycholic acid 3-sulfate

Description

Chenodeoxycholic acid 3-sulfate, also known as 3-sulfochenodeoxycholate or CDCS, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Chenodeoxycholic acid 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

7-Sulfocholyltaurine.mol
  Mrv0541 02231219332D          

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7-Sulfocholyltaurine.mol
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 16 26  1  0  0  0  0
  7 27  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 28 29  1  0  0  0  0
  1 28  1  6  0  0  0
  5 33  1  1  0  0  0
 22 34  1  6  0  0  0
  8 35  1  1  0  0  0
  9 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086993

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

> <INCHI_KEY>
WHMOBEGYTDWMIG-BSWAIDMHSA-N

> <FORMULA>
C24H40O7S

> <MOLECULAR_WEIGHT>
472.635

> <EXACT_MASS>
472.249474324

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
51.88292797876075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
2.321619271901573

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.595945681139674

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4705842836832614

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5428097932948205

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
119.26559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7-Sulfocholyltaurine.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.247  -4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.247  -2.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.913  -2.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.913  -5.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.580  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.754  -5.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.088  -4.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.088  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.421  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.886  -2.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.791  -1.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.886  -0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.362   1.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.273   2.523   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.672   4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.159   4.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.868   1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.421  -0.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.421   1.033   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.088   0.263   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.754  -0.507   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.754  -2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.580  -2.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.580  -1.277   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.558   5.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.248   3.320   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.421  -5.127   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.581  -5.127   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0      -5.914  -4.357   0.000  0.00  0.00           S+0
HETATM   30  O   UNK     0      -5.144  -3.023   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.684  -5.690   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.248  -3.587   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      -0.580  -5.897   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.754  -3.587   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.088  -1.277   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.421  -3.587   0.000  0.00  0.00           H+0
CONECT    1    2    4   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   22   35                                             
CONECT    9    8   10   18   36                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   34                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    7                                                            
CONECT   28   29    1                                                       
CONECT   29   30   31   32   28                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33    5                                                            
CONECT   34   22                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Chenodeoxycholate 3-sulfate	Generator
Chenodeoxycholate 3-sulphate	Generator
Chenodeoxycholic acid 3-sulfuric acid	Generator
Chenodeoxycholic acid 3-sulphuric acid	Generator
3-Sulfochenodeoxycholate	HMDB
3-Sulfochenodeoxycholic acid	HMDB
Chenodeoxycholic acid 3-sulphate	HMDB
Chenodeoxycholic acid 3a-sulfate	HMDB
Chenodeoxycholic acid 3a-sulphate	HMDB
CDCS	HMDB
Chenodeoxycholate sulfate conjugate	HMDB
Chenodeoxycholic acid sulfate conjugate	HMDB

Chemical Formula

C₂₄H₄₀O₇S

Average Mass

472.6350 Da

Monoisotopic Mass

472.24947 Da

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

WHMOBEGYTDWMIG-BSWAIDMHSA-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 monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
Hydroxysteroid
7-hydroxysteroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Cyclic alcohol
Organic sulfuric acid or derivatives
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Sulfates (LMST05020024 )

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	0.49	ALOGPS
logP	2.32	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.27 m³·mol⁻¹	ChemAxon
Polarizability	51.88 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

HMDB0002586

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023031

KNApSAcK ID

Not Available

Chemspider ID

13628372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6719

PubChem Compound

21252312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Chenodeoxycholic acid 3-sulfate (NP0086993)

MOL for NP0086993 (Chenodeoxycholic acid 3-sulfate)

3D MOL for NP0086993 (Chenodeoxycholic acid 3-sulfate)

3D SDF for NP0086993 (Chenodeoxycholic acid 3-sulfate)

3D-SDF for NP0086993 (Chenodeoxycholic acid 3-sulfate)

PDB for NP0086993 (Chenodeoxycholic acid 3-sulfate)

3D PDB for NP0086993 (Chenodeoxycholic acid 3-sulfate)

SMILES for NP0086993 (Chenodeoxycholic acid 3-sulfate)

INCHI for NP0086993 (Chenodeoxycholic acid 3-sulfate)

Structure for NP0086993 (Chenodeoxycholic acid 3-sulfate)

3D Structure for NP0086993 (Chenodeoxycholic acid 3-sulfate)