NP-MRD: Showing NP-Card for {[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium (NP0153325)

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Record Information

Version

2.0

Created at

2022-09-02 09:57:33 UTC

Updated at

2022-09-02 09:57:33 UTC

NP-MRD ID

NP0153325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium

Description

Epimuscarine belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. {[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium is found in Inocybe geophylla. Based on a literature review very few articles have been published on Epimuscarine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    2.5115   -1.2636    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0321   -0.7819   -0.5972 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6655   -0.6928   -0.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.6124   -0.3956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7880    0.7375    0.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -0.0288    0.2123 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3004    0.2099   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0516    0.3388    1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -1.4532    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5313    1.4088   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    0.6280   -0.8775 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8346    0.8177   -0.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870   -1.8193    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740   -1.9605    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8223   -0.4487    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -1.4387   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    1.0281   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203    1.7679    0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875    0.2340    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    1.2485   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054    0.0187   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8377   -0.5338   -1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5921   -0.5403    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660    1.0045    0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7196    0.9335    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -1.8506   -0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998   -1.9203    0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018   -1.6891    1.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    1.3228    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748    2.4616   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3502    0.8540   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    0.7950   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  6
  4 17  1  6
  5 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
M  CHG  1   6   1
M  END


  Mrv1652309022211572D          

 12 12  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -1.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1994    0.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  CHG  1   6   1
M  END
> <DATABASE_ID>
NP0153325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](C[N+](C)(C)C)C[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9-/m1/s1

> <INCHI_KEY>
UQOFGTXDASPNLL-IWSPIJDZSA-N

> <FORMULA>
C9H20NO2

> <MOLECULAR_WEIGHT>
174.263

> <EXACT_MASS>
174.148855308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.286273519927903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,4R,5R)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium

> <ALOGPS_LOGP>
-2.98

> <JCHEM_LOGP>
-4.284700710805079

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.11178387341359

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1873057337688957

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
59.893100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,4R,5R)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.267  -1.375   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0       5.798  -1.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.428  -2.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.106   0.157   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
(+)-Epimuscarine	MeSH

Chemical Formula

C₉H₂₀NO₂

Average Mass

174.2630 Da

Monoisotopic Mass

174.14886 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](C[N+](C)(C)C)C[C@H]1O

InChI Identifier

InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9-/m1/s1

InChI Key

UQOFGTXDASPNLL-IWSPIJDZSA-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
Inocybe geophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Quaternary ammonium salt
Tetraalkylammonium salt
Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organic salt
Alcohol
Organic cation
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

78443818

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14337615

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium (NP0153325)

MOL for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

3D MOL for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

3D SDF for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

3D-SDF for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

PDB for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

3D PDB for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

SMILES for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

INCHI for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

Structure for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)

3D Structure for NP0153325 ({[(2r,4r,5r)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium)