NP-MRD: Showing NP-Card for [(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid (NP0178301)

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Record Information

Version

2.0

Created at

2022-09-03 16:16:16 UTC

Updated at

2022-09-03 16:16:16 UTC

NP-MRD ID

NP0178301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid

Description

Acanthosterol sulfate C belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Based on a literature review very few articles have been published on Acanthosterol sulfate C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218162D          

 35 39  0  0  1  0            999 V2000
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   -0.3431   -3.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0933   -2.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032218162D          

 35 39  0  0  1  0            999 V2000
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    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  6  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 14  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0178301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1O[C@H]1[C@@H](C)[C@H]1CC[C@H]2C3=CCC4[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O7S/c1-14(2)12-22-24(33-22)15(3)17-8-9-18-16-6-7-20-25(34-35(30,31)32)23(29)21(28)13-27(20,5)19(16)10-11-26(17,18)4/h6,14-15,17-25,28-29H,7-13H2,1-5H3,(H,30,31,32)/t15-,17+,18-,19-,20?,21+,22-,23-,24-,25-,26+,27+/m0/s1

> <INCHI_KEY>
XRRWYIVUOJEZDH-FTAPDTLJSA-N

> <FORMULA>
C27H44O7S

> <MOLECULAR_WEIGHT>
512.7

> <EXACT_MASS>
512.280774931

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.42642095964584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,4R,5S,6S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-14-[(1S)-1-[(2S,3S)-3-(2-methylpropyl)oxiran-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-6-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
2.4159316230658456

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.135292041329084

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4977143040771024

> <JCHEM_PKA_STRONGEST_BASIC>
-3.190778102376435

> <JCHEM_POLAR_SURFACE_AREA>
116.59

> <JCHEM_REFRACTIVITY>
132.6982

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,4R,5S,6S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-14-[(1S)-1-[(2S,3S)-3-(2-methylpropyl)oxiran-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-6-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.586  -8.454   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.640  -7.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.221  -5.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.885  -7.448   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -6.233   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.041  -4.707   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0      13.384   0.461   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0      12.391   1.639   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.561   1.454   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.207  -0.531   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   17   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   14   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   13   10   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Acanthosterol sulfuric acid C	Generator
Acanthosterol sulphate C	Generator
Acanthosterol sulphuric acid C	Generator

Chemical Formula

C₂₇H₄₄O₇S

Average Mass

512.7000 Da

Monoisotopic Mass

512.28077 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1O[C@H]1[C@@H](C)[C@H]1CC[C@H]2C3=CCC4[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O7S/c1-14(2)12-22-24(33-22)15(3)17-8-9-18-16-6-7-20-25(34-35(30,31)32)23(29)21(28)13-27(20,5)19(16)10-11-26(17,18)4/h6,14-15,17-25,28-29H,7-13H2,1-5H3,(H,30,31,32)/t15-,17+,18-,19-,20?,21+,22-,23-,24-,25-,26+,27+/m0/s1

InChI Key

XRRWYIVUOJEZDH-FTAPDTLJSA-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 cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Sulfated steroid skeleton
12-beta-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
2-hydroxysteroid
12-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Cyclitol or derivatives
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

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

8849230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10673880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid (NP0178301)

MOL for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D MOL for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D SDF for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D-SDF for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

PDB for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D PDB for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

SMILES for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

INCHI for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

Structure for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D Structure for NP0178301 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-9a,11a-dimethyl-1-[(1s)-1-[(2s,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)