NP-MRD: Showing NP-Card for 5b-Cyprinol sulfate (NP0087665)

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Record Information

Version

2.0

Created at

2022-05-11 16:56:18 UTC

Updated at

2022-05-11 16:56:18 UTC

NP-MRD ID

NP0087665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5b-Cyprinol sulfate

Description

5B-Cyprinol sulfate belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 5B-Cyprinol sulfate is an intermediate in bile acid biosynthesis. 5B-Cyprinol sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 5b-cyprinol sulfate is involved in cerebrotendinous xanthomatosis (ctx). They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220542D          

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M  END

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M  END


  Mrv0541 02231220542D          

 36 39  0  0  1  0            999 V2000
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   11.3721  -12.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6589  -12.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9444   -9.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8683   -3.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6420   -4.9956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7031   -3.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072   -5.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2551   -4.4435    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
 26  2  1  1  0  0  0
 27  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7 20  1  0  0  0  0
  7  8  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  1  0  0  0  0
  9 19  1  0  0  0  0
 10 26  1  0  0  0  0
 11 19  1  0  0  0  0
 11 18  1  0  0  0  0
 12 18  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  1  0  0  0  0
 13 24  1  0  0  0  0
 14 17  1  0  0  0  0
 14 28  1  0  0  0  0
 15 17  1  0  0  0  0
 15 35  1  0  0  0  0
 16 20  1  0  0  0  0
 18 26  1  0  0  0  0
 19 29  1  6  0  0  0
 20 27  1  0  0  0  0
 21 25  1  0  0  0  0
 21 27  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 25  1  0  0  0  0
 23 30  1  6  0  0  0
 24 31  1  1  0  0  0
 24 27  1  0  0  0  0
 32 36  1  0  0  0  0
 33 36  2  0  0  0  0
 34 36  2  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O8S/c1-16(5-4-6-17(14-28)15-35-36(32,33)34)20-7-8-21-25-22(13-24(31)27(20,21)3)26(2)10-9-19(29)11-18(26)12-23(25)30/h16-25,28-31H,4-15H2,1-3H3,(H,32,33,34)/t16?,17?,18?,19-,20?,21?,22?,23-,24-,25?,26+,27-/m1/s1

> <INCHI_KEY>
KAOLEMQCYWHOJQ-UQACNIHJSA-N

> <FORMULA>
C27H48O8S

> <MOLECULAR_WEIGHT>
532.73

> <EXACT_MASS>
532.306989202

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
59.39218434185373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxy)sulfonic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.6316805351820279

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.397308745750092

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7771056690233298

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13939311435437662

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
136.54789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      32.677 -16.946   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.932 -19.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.500 -17.691   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.616 -14.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.140 -16.122   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.585 -13.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.600 -19.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.695 -21.223   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.561 -21.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.895 -20.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.895 -23.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.563 -23.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.563 -19.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.568 -11.728   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.031 -10.904   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.171 -17.266   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.061 -12.048   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.229 -23.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.561 -23.057   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.695 -18.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.230 -20.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.563 -20.747   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.896 -23.057   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.896 -18.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.896 -21.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.229 -21.517   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.230 -19.207   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      32.044 -10.263   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      21.228 -23.827   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      29.230 -23.827   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      27.896 -16.897   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      29.621  -7.264   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      27.332  -9.325   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      27.446  -7.150   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      29.507  -9.439   0.000  0.00  0.00           O+0
HETATM   36  S   UNK     0      28.476  -8.295   0.000  0.00  0.00           S+0
CONECT    1   16                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    5    6                                                       
CONECT    5    4   16                                                       
CONECT    6    4   17                                                       
CONECT    7   20    8                                                       
CONECT    8    7   21                                                       
CONECT    9   10   19                                                       
CONECT   10    9   26                                                       
CONECT   11   19   18                                                       
CONECT   12   18   23                                                       
CONECT   13   22   24                                                       
CONECT   14   17   28                                                       
CONECT   15   17   35                                                       
CONECT   16    1    5   20                                                  
CONECT   17    6   14   15                                                  
CONECT   18   11   12   26                                                  
CONECT   19    9   11   29                                                  
CONECT   20    7   16   27                                                  
CONECT   21    8   25   27                                                  
CONECT   22   13   25   26                                                  
CONECT   23   12   25   30                                                  
CONECT   24   13   31   27                                                  
CONECT   25   21   22   23                                                  
CONECT   26    2   10   18   22                                             
CONECT   27    3   20   21   24                                             
CONECT   28   14                                                            
CONECT   29   19                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   36                                                            
CONECT   33   36                                                            
CONECT   34   36                                                            
CONECT   35   15   36                                                       
CONECT   36   32   33   34   35                                             
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
5b-Cyprinol sulfuric acid	Generator
5b-Cyprinol sulphate	Generator
5b-Cyprinol sulphuric acid	Generator
5b-Cyprinosulfate	HMDB
5b-Cyprinosulphate	HMDB
5beta-Cyprinol sulfate	HMDB
5beta-Cyprinol sulphate	HMDB
5beta-Cyprinolsulfate	HMDB
5beta-Cyprinolsulphate	HMDB

Chemical Formula

C₂₇H₄₈O₈S

Average Mass

532.7300 Da

Monoisotopic Mass

532.30699 Da

IUPAC Name

(3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxy)sulfonic acid

Traditional Name

3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxysulfonic acid

CAS Registry Number

Not Available

SMILES

CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C

InChI Identifier

InChI=1S/C27H48O8S/c1-16(5-4-6-17(14-28)15-35-36(32,33)34)20-7-8-21-25-22(13-24(31)27(20,21)3)26(2)10-9-19(29)11-18(26)12-23(25)30/h16-25,28-31H,4-15H2,1-3H3,(H,32,33,34)/t16?,17?,18?,19-,20?,21?,22?,23-,24-,25?,26+,27-/m1/s1

InChI Key

KAOLEMQCYWHOJQ-UQACNIHJSA-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 tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Tetrahydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Sulfate-ester
Sulfuric acid monoester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Primary alcohol
Organooxygen compound
Organic oxygen compound
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	0.77	ALOGPS
logP	0.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-0.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.55 m³·mol⁻¹	ChemAxon
Polarizability	59.39 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

HMDB0006888

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024135

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05468

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477904

PDB ID

Not Available

ChEBI ID

2149

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5b-Cyprinol sulfate (NP0087665)

MOL for NP0087665 (5b-Cyprinol sulfate)

3D MOL for NP0087665 (5b-Cyprinol sulfate)

3D SDF for NP0087665 (5b-Cyprinol sulfate)

3D-SDF for NP0087665 (5b-Cyprinol sulfate)

PDB for NP0087665 (5b-Cyprinol sulfate)

3D PDB for NP0087665 (5b-Cyprinol sulfate)

SMILES for NP0087665 (5b-Cyprinol sulfate)

INCHI for NP0087665 (5b-Cyprinol sulfate)

Structure for NP0087665 (5b-Cyprinol sulfate)

3D Structure for NP0087665 (5b-Cyprinol sulfate)