NP-MRD: Showing NP-Card for [(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid (NP0288299)

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Record Information

Version

2.0

Created at

2022-09-09 17:57:02 UTC

Updated at

2022-09-09 17:57:02 UTC

NP-MRD ID

NP0288299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Acanthosterol sulfate A belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Based on a literature review very few articles have been published on Acanthosterol sulfate A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219572D          

 34 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092219572D          

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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 13  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0288299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(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/C26H42O7S/c1-13(2)22-23(32-22)14(3)16-8-9-17-15-6-7-19-24(33-34(29,30)31)21(28)20(27)12-26(19,5)18(15)10-11-25(16,17)4/h6,13-14,16-24,27-28H,7-12H2,1-5H3,(H,29,30,31)/t14-,16+,17-,18-,19?,20+,21-,22-,23-,24-,25+,26+/m0/s1

> <INCHI_KEY>
QVIGQAGJGQDQPQ-KFWMQUQESA-N

> <FORMULA>
C26H42O7S

> <MOLECULAR_WEIGHT>
498.68

> <EXACT_MASS>
498.265124866

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.25075285993178

> <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-(propan-2-yl)oxiran-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-6-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
2.0493170285361497

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.135292041329084

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.497717854181852

> <JCHEM_PKA_STRONGEST_BASIC>
-3.190778102376435

> <JCHEM_POLAR_SURFACE_AREA>
116.59

> <JCHEM_REFRACTIVITY>
128.0202

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.640  -7.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.885  -7.448   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465  -8.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -6.233   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.041  -4.707   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0      13.384   0.461   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0      12.391   1.639   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.561   1.454   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.207  -0.531   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   34  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    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   16   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   13   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   12    9   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₆H₄₂O₇S

Average Mass

498.6800 Da

Monoisotopic Mass

498.26512 Da

IUPAC Name

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

Traditional Name

[(1R,2R,4R,5S,6S,11R,14R,15R)-4,5-dihydroxy-14-[(1S)-1-[(2S,3S)-3-isopropyloxiran-2-yl]ethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-6-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC(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/C26H42O7S/c1-13(2)22-23(32-22)14(3)16-8-9-17-15-6-7-19-24(33-34(29,30)31)21(28)20(27)12-26(19,5)18(15)10-11-25(16,17)4/h6,13-14,16-24,27-28H,7-12H2,1-5H3,(H,29,30,31)/t14-,16+,17-,18-,19?,20+,21-,22-,23-,24-,25+,26+/m0/s1

InChI Key

QVIGQAGJGQDQPQ-KFWMQUQESA-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 sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Androgen-skeleton
Androstane-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
logP	2.05	ChemAxon
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.02 m³·mol⁻¹	ChemAxon
Polarizability	55.25 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

8896107

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10720769

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-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid (NP0288299)

MOL for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D MOL for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D SDF for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D-SDF for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

PDB for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D PDB for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

SMILES for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

INCHI for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

Structure for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)

3D Structure for NP0288299 ([(1r,3ar,6s,7s,8r,9ar,9br,11ar)-7,8-dihydroxy-1-[(1s)-1-[(2s,3s)-3-isopropyloxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl]oxidanesulfonic acid)