NP-MRD: Showing NP-Card for eurysterol a sulfonic acid (NP0263175)

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Record Information

Version

2.0

Created at

2022-09-08 06:16:16 UTC

Updated at

2022-09-08 06:16:17 UTC

NP-MRD ID

NP0263175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eurysterol a sulfonic acid

Description

Eurysterol A sulfonic acid, also known as eurysterol a hydrogen sulfate or eurysterol a sulphonate, belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. Based on a literature review very few articles have been published on eurysterol A sulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082208162D          

 35 39  0  0  1  0            999 V2000
    9.2112    3.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4025    3.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8569    4.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  1  0  0  0
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 18 35  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082208162D          

 35 39  0  0  1  0            999 V2000
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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 17 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 18 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0263175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@]34CO[C@]21C[C@@H](O)[C@@]3(O)C[C@H](CC4)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O7S/c1-17(2)6-5-7-18(3)20-8-9-21-24(20,4)12-11-22-25-13-10-19(34-35(30,31)32)14-27(25,29)23(28)15-26(21,22)33-16-25/h17-23,28-29H,5-16H2,1-4H3,(H,30,31,32)/t18-,19+,20-,21-,22-,23-,24-,25+,26-,27+/m1/s1

> <INCHI_KEY>
MWTQCWZOXMULHF-QZSJCTLHSA-N

> <FORMULA>
C27H46O7S

> <MOLECULAR_WEIGHT>
514.72

> <EXACT_MASS>
514.296424995

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.4789179183975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,5R,6R,9R,10R,12R,13R,15S)-12,13-dihydroxy-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[8.7.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-15-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
2.3604877493189225

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.203363137550202

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.612236850799726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2875161881141493

> <JCHEM_POLAR_SURFACE_AREA>
113.28999999999999

> <JCHEM_REFRACTIVITY>
132.35339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,5R,6R,9R,10R,12R,13R,15S)-12,13-dihydroxy-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[8.7.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-15-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      17.194   7.004   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.685   6.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.666   7.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.193   5.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.684   4.936   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.193   3.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.683   3.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.665   4.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.192   1.712   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.084   0.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.166  -0.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.706  -0.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.722   1.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.899   2.781   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.397   2.035   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.843   1.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.039  -0.261   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.365  -1.045   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.387  -2.348   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.791  -2.326   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.957  -3.621   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.100  -0.858   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.293  -2.170   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.543  -0.902   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.735   0.416   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.196   0.367   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0       0.468  -0.990   0.000  0.00  0.00           S+0
HETATM   28  O   UNK     0      -0.259  -2.347   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.889  -0.262   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.826  -1.718   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.460   1.784   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.016   1.834   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.956   0.548   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.335   1.504   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.684   0.586   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12    9   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   12   19   35                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   33                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   25   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   17   22   34                                             
CONECT   34   33   35                                                       
CONECT   35   34   18                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(3beta,5alpha,6beta)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulfonic acid	ChEBI
Eurysterol a hydrogen sulfate	ChEBI
(3b,5a,6b)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulfonate	Generator
(3b,5a,6b)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulfonic acid	Generator
(3b,5a,6b)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulphonate	Generator
(3b,5a,6b)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulphonic acid	Generator
(3beta,5alpha,6beta)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulfonate	Generator
(3beta,5alpha,6beta)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulphonate	Generator
(3beta,5alpha,6beta)-5,6-Dihydroxy-8,19-epoxycholestan-3-yl sulphonic acid	Generator
(3Β,5α,6β)-5,6-dihydroxy-8,19-epoxycholestan-3-yl sulfonate	Generator
(3Β,5α,6β)-5,6-dihydroxy-8,19-epoxycholestan-3-yl sulfonic acid	Generator
(3Β,5α,6β)-5,6-dihydroxy-8,19-epoxycholestan-3-yl sulphonate	Generator
(3Β,5α,6β)-5,6-dihydroxy-8,19-epoxycholestan-3-yl sulphonic acid	Generator
Eurysterol a hydrogen sulfuric acid	Generator
Eurysterol a hydrogen sulphate	Generator
Eurysterol a hydrogen sulphuric acid	Generator
Eurysterol a sulfonate	Generator
Eurysterol a sulphonate	Generator
Eurysterol a sulphonic acid	Generator

Chemical Formula

C₂₇H₄₆O₇S

Average Mass

514.7200 Da

Monoisotopic Mass

514.29642 Da

IUPAC Name

[(1R,2R,5R,6R,9R,10R,12R,13R,15S)-12,13-dihydroxy-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[8.7.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-15-yl]oxidanesulfonic acid

Traditional Name

[(1R,2R,5R,6R,9R,10R,12R,13R,15S)-12,13-dihydroxy-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[8.7.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-15-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@]34CO[C@]21C[C@@H](O)[C@@]3(O)C[C@H](CC4)OS(O)(=O)=O

InChI Identifier

InChI=1S/C27H46O7S/c1-17(2)6-5-7-18(3)20-8-9-21-24(20,4)12-11-22-25-13-10-19(34-35(30,31)32)14-27(25,29)23(28)15-26(21,22)33-16-25/h17-23,28-29H,5-16H2,1-4H3,(H,30,31,32)/t18-,19+,20-,21-,22-,23-,24-,25+,26-,27+/m1/s1

InChI Key

MWTQCWZOXMULHF-QZSJCTLHSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Cholane-skeleton
Oxepane
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Cyclic alcohol
Organic sulfuric acid or derivatives
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:68591 )
organic heteropentacyclic compound (CHEBI:68591 )
diol (CHEBI:68591 )
bridged compound (CHEBI:68591 )
cyclic ether (CHEBI:68591 )
5alpha-hydroxy steroid (CHEBI:68591 )
6beta-hydroxy steroid (CHEBI:68591 )

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	2.36	ChemAxon
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.35 m³·mol⁻¹	ChemAxon
Polarizability	58.48 Å³	ChemAxon
Number of Rings	5	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

17614087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16681436

PDB ID

Not Available

ChEBI ID

68591

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for eurysterol a sulfonic acid (NP0263175)

MOL for NP0263175 (eurysterol a sulfonic acid)

3D MOL for NP0263175 (eurysterol a sulfonic acid)

3D SDF for NP0263175 (eurysterol a sulfonic acid)

3D-SDF for NP0263175 (eurysterol a sulfonic acid)

PDB for NP0263175 (eurysterol a sulfonic acid)

3D PDB for NP0263175 (eurysterol a sulfonic acid)

SMILES for NP0263175 (eurysterol a sulfonic acid)

INCHI for NP0263175 (eurysterol a sulfonic acid)

Structure for NP0263175 (eurysterol a sulfonic acid)

3D Structure for NP0263175 (eurysterol a sulfonic acid)