NP-MRD: Showing NP-Card for [(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid (NP0248565)

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Record Information

Version

2.0

Created at

2022-09-07 10:51:57 UTC

Updated at

2022-09-07 10:51:57 UTC

NP-MRD ID

NP0248565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid

Description

Cholestanol sulfate belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. [(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid is found in Eupentacta fraudatrix. Based on a literature review a small amount of articles have been published on cholestanol sulfate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072212512D          

 32 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072212512D          

 32 35  0  0  1  0            999 V2000
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 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  1  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)COS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O4S/c1-19(18-31-32(28,29)30)8-7-9-20(2)23-13-14-24-22-12-11-21-10-5-6-16-26(21,3)25(22)15-17-27(23,24)4/h19-25H,5-18H2,1-4H3,(H,28,29,30)/t19?,20-,21?,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
WEPXUGVQGGWSIU-GIAGXXIISA-N

> <FORMULA>
C27H48O4S

> <MOLECULAR_WEIGHT>
468.74

> <EXACT_MASS>
468.3273312

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.72351990785177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl]oxy}sulfonic acid

> <JCHEM_LOGP>
7.601447920333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3921511952841392

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
129.94049999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      13.284   2.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.284   0.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.617  -0.221   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.951   0.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.285  -0.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.618   0.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.618   2.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.952  -0.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.359   0.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.389  -0.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.619  -2.072   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.095  -3.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.602  -3.857   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.077  -5.322   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.047  -6.466   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.523  -7.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.492  -9.075   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.986  -8.755   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.510  -7.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.541  -6.146   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.034  -5.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.065  -4.681   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.558  -4.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.083  -2.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.113  -1.752   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.648  -1.276   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.950  -0.221   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.616   0.549   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0       9.283  -0.221   0.000  0.00  0.00           S+0
HETATM   30  O   UNK     0       7.949  -0.991   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.513   1.113   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.053  -1.554   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   12   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   11    8   26                                             
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Cholestanol sulfuric acid	Generator
Cholestanol sulphate	Generator
Cholestanol sulphuric acid	Generator

Chemical Formula

C₂₇H₄₈O₄S

Average Mass

468.7400 Da

Monoisotopic Mass

468.32733 Da

IUPAC Name

{[(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl]oxy}sulfonic acid

Traditional Name

[(6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptyl]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)COS(O)(=O)=O

InChI Identifier

InChI=1S/C27H48O4S/c1-19(18-31-32(28,29)30)8-7-9-20(2)23-13-14-24-22-12-11-21-10-5-6-16-26(21,3)25(22)15-17-27(23,24)4/h19-25H,5-18H2,1-4H3,(H,28,29,30)/t19?,20-,21?,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

WEPXUGVQGGWSIU-GIAGXXIISA-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
Eupentacta fraudatrix	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Bile acids, alcohols and derivatives

Alternative Parents

Substituents

Bile acid, alcohol, or derivatives
Sulfated steroid skeleton
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	7.6	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.94 m³·mol⁻¹	ChemAxon
Polarizability	56.72 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129671354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid (NP0248565)

MOL for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

3D MOL for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

3D SDF for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

3D-SDF for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

PDB for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

3D PDB for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

SMILES for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

INCHI for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

Structure for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)

3D Structure for NP0248565 ([(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptyl]oxysulfonic acid)