NP-MRD: Showing NP-Card for Muscarine (NP0045032)

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Record Information

Version

1.0

Created at

2022-03-10 18:53:03 UTC

Updated at

2022-03-10 22:21:48 UTC

NP-MRD ID

NP0045032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Muscarine

Description

Muscarine or (2S,4R,5S)-Muscarine, L-(+)-muscarine, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Muscarine is also a quaternary ammonium salt that is soluble in water. Muscarine is also a proto alkaloid, a class of nitrogenous organic compounds of plant origin¬¨‚Ä†with pronounced effects on humans. It is a natural product of some mushroom species, particularly in the genera Inocybe and Clitocybe (PMID: 27714029 ). Muscarine is also found in cannabis plants (PMID: 6991645 ). Muscarine can cause profound activation of the¬¨‚Ä†peripheral¬¨‚Ä†parasympathetic nervous system¬¨‚Ä†that may end in circulatory collapse and death. Muscarine is a nonselective agonist of the muscarinic acetylcholine receptors. Muscarine and muscarine agonists are used for the treatment of glaucoma, urinary retention, postoperative ileus, xerostomia and congenital megacolon. However, muscarine and its agonists are contraindicated for those who are sensitive to parasympathetic stimulation such as people with asthma, Chronic Obstructive Pulmonary disease (COPD), peptic ulcer disease or those with obstructions to the gastrointestinal tract or urinary tract. Muscarine is not metabolized by the body and is removed by renal clearance.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    2.8542    0.8469   -1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401   -0.2942   -0.9044 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7993   -0.0241   -0.8125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -0.4085    0.4520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8812    0.3098    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    0.0830   -0.0044 N   0  0  1  0  0  4  0  0  0  0  0  0
   -2.2625   -1.3022   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1787    0.6399    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    0.7925   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041    0.1142    1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940   -0.3756    0.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0352   -1.6882    0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7195    1.7560   -0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382    0.6157   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4437    0.9665   -2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111   -1.2310   -1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -1.4919    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1563   -0.0705    1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952    1.3828    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8861   -1.5590   -1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691   -1.9741    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -1.4743   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397    0.4850    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    0.0944    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    1.7125    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3678    1.7641   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2188    0.2494   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8506    0.9636   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927    1.2138    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838   -0.2753    2.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346    0.3008    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133   -2.1223   -0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  1
  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
  2 16  1  6
  1 13  1  0
  1 14  1  0
  1 15  1  0
  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


  Mrv1652303202019012D          

 15 15  0  0  1  0            999 V2000
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658    3.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  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
    0.9803   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596   -0.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -0.8903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  6  0  0  0
  8  5  1  0  0  0  0
  8  6  1  6  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
  9 11  1  1  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  1  0  0  0
  9 15  1  6  0  0  0
M  CHG  1  10   1
M  END
> <DATABASE_ID>
NP0045032

> <DATABASE_NAME>
NP-MRD

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

> <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+/m0/s1

> <INCHI_KEY>
UQOFGTXDASPNLL-XHNCKOQMSA-N

> <FORMULA>
C9H20NO2

> <MOLECULAR_WEIGHT>
174.2601

> <EXACT_MASS>
174.148855309

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.10146678640744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,4R,5S)-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>
(+)-muscarine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.608   5.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.496   5.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.044   3.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.274   4.390   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      -1.231  -0.049   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.312   2.779   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.131  -1.662   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1    9   12   13                                             
CONECT    8    5    6   12   14                                             
CONECT    9    5    7   11   15                                             
CONECT   10    2    3    4    6                                             
CONECT   11    9                                                            
CONECT   12    7    8                                                       
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Muscarin	ChEMBL
L-(+)-Muscarine	ChEMBL

Chemical Formula

C₉H₂₀NO₂

Average Mass

174.2601 Da

Monoisotopic Mass

174.14886 Da

IUPAC Name

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

Traditional Name

(+)-muscarine

CAS Registry Number

300-54-9

SMILES

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

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+/m0/s1

InChI Key

UQOFGTXDASPNLL-XHNCKOQMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Amanita cothurnata	Fungi	KNApSAcK
Amanita gemmata	Fungi	KNApSAcK
Amanita muscaria	Fungi	KNApSAcK
Amanita pantherina	Fungi	KNApSAcK
Amanita smithiana	Fungi	KNApSAcK
Amanita strobiliformis	Fungi	KNApSAcK
Cannabis sativa	NULL	Not Available
Clitocybe spp.	Fungi	KNApSAcK
Entoloma rhodopolium	LOTUS Database	35616633
Inocybe imbrina	Fungi	KNApSAcK
Inocybe napipes	Fungi	KNApSAcK
Inocybe obscuroides	Fungi	KNApSAcK

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

monosaccharide (CHEBI:7034 )
Alkaloids (C07473 )

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	-3	ALOGPS
logP	-4.3	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.11	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.89 m³·mol⁻¹	ChemAxon
Polarizability	20.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00001422

Chemspider ID

Not Available

KEGG Compound ID

C07473

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9308

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Jin Z: Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep. 2016 Oct 26;33(11):1268-1317. doi: 10.1039/c6np00067c. [PubMed:27714029 ]

Showing NP-Card for Muscarine (NP0045032)

MOL for NP0045032 (Muscarine)

3D MOL for NP0045032 (Muscarine)

3D SDF for NP0045032 (Muscarine)

3D-SDF for NP0045032 (Muscarine)

PDB for NP0045032 (Muscarine)

3D PDB for NP0045032 (Muscarine)

SMILES for NP0045032 (Muscarine)

INCHI for NP0045032 (Muscarine)

Structure for NP0045032 (Muscarine)

3D Structure for NP0045032 (Muscarine)