NP-MRD: Showing NP-Card for Muscimol (NP0021691)

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Record Information

Version

1.0

Created at

2021-01-06 06:57:58 UTC

Updated at

2021-07-15 17:37:01 UTC

NP-MRD ID

NP0021691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Muscimol

Provided By

NPAtlas

Description

Muscimol, also known as agarin or pantherine, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Muscimol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Muscimol is found in Amanita muscaria. It was first documented in 1967 (PMID: 5629522). Based on a literature review a significant number of articles have been published on Muscimol (PMID: 18599311) (PMID: 21427702) (PMID: 21751026) (PMID: 2181052).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105173D          

 14 14  0  0  0  0            999 V2000
    2.2255   -0.5258    0.4221 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.4833    0.2705   -0.5567 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0258   -0.0003   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.6991    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840    0.1444    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537    0.4891    0.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -0.8622   -0.5422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.9131   -0.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1571   -0.0876    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -0.6430    1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8306   -0.0018   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    1.3606   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6011    1.5444    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575   -1.4743   -0.8282 H   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  3  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  4 13  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C([H])([H])C1=C([H])C(=O)N([H])O1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)

> <INCHI_KEY>
ZJQHPWUVQPJPQT-UHFFFAOYSA-N

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.1026

> <EXACT_MASS>
114.042927446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.486868510779635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(aminomethyl)-2,3-dihydro-1,2-oxazol-3-one

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-2.212104713046448

> <ALOGPS_LOGS>
0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.860723678152463

> <JCHEM_PKA_STRONGEST_BASIC>
8.965556056467365

> <JCHEM_POLAR_SURFACE_AREA>
64.35000000000001

> <JCHEM_REFRACTIVITY>
28.0972

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
muscimol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0       2.225  -0.526   0.422  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.483   0.271  -0.557  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.026  -0.000  -0.371  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.825   0.699   0.465  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.084   0.144   0.354  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.154   0.489   0.951  0.00  0.00           O+0
HETATM    7  N   UNK     0      -1.938  -0.862  -0.542  0.00  0.00           N+0
HETATM    8  O   UNK     0      -0.716  -0.913  -0.934  0.00  0.00           O+0
HETATM    9  H   UNK     0       3.157  -0.088   0.601  0.00  0.00           H+0
HETATM   10  H   UNK     0       1.649  -0.643   1.281  0.00  0.00           H+0
HETATM   11  H   UNK     0       1.831  -0.002  -1.575  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.705   1.361  -0.386  0.00  0.00           H+0
HETATM   13  H   UNK     0      -0.601   1.544   1.119  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.757  -1.474  -0.828  0.00  0.00           H+0
CONECT    1    2    9   10                                                  
CONECT    2    1    3   11   12                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    3                                                       
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    2                                                            
CONECT   12    2                                                            
CONECT   13    4                                                            
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-(Aminomethyl)-3(2H)-isoxazolone	ChEBI
Agarin	HMDB
Pantherine	HMDB

Chemical Formula

C₄H₆N₂O₂

Average Mass

114.1026 Da

Monoisotopic Mass

114.04293 Da

IUPAC Name

5-(aminomethyl)-2,3-dihydro-1,2-oxazol-3-one

Traditional Name

muscimol

CAS Registry Number

Not Available

SMILES

NCC1=CC(=O)NO1

InChI Identifier

InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)

InChI Key

ZJQHPWUVQPJPQT-UHFFFAOYSA-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 muscaria	NPAtlas	5629522

Species Where Detected

Species Name	Source	Reference
Amanita cothurnata	KNApSAcK Database	22123792
Amanita gemmata	KNApSAcK Database	22123792
Amanita pantherina	KNApSAcK Database	22123792
Amanita smithiana	KNApSAcK Database	22123792
Amanita strobiliformis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic 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
logP	-1.6	ALOGPS
logP	-2.2	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	5.86	ChemAxon
pKa (Strongest Basic)	8.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.1 m³·mol⁻¹	ChemAxon
Polarizability	10.49 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA024780

HMDB ID

HMDB0254955

DrugBank ID

DB12458

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001423

Chemspider ID

4116

KEGG Compound ID

C08311

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Muscimol

METLIN ID

Not Available

PubChem Compound

4266

PDB ID

Not Available

ChEBI ID

7035

Good Scents ID

Not Available

References

General References

Eugster CH: Isolation, structure, and syntheses of central-active compounds from Amanita muscaria (L. ex Fr.) hooker. Psychopharmacol Bull. 1967 Dec;4(3):18-9. [PubMed:5629522 ]
Doi M, Iwasaki K: Na+/K+ ATPase regulates the expression and localization of acetylcholine receptors in a pump activity-independent manner. Mol Cell Neurosci. 2008 Aug;38(4):548-58. doi: 10.1016/j.mcn.2008.05.003. Epub 2008 May 16. [PubMed:18599311 ]
Bellemer A, Hirata T, Romero MF, Koelle MR: Two types of chloride transporters are required for GABA(A) receptor-mediated inhibition in C. elegans. EMBO J. 2011 May 4;30(9):1852-63. doi: 10.1038/emboj.2011.83. Epub 2011 Mar 22. [PubMed:21427702 ]
Stribrny J, Sokol M, Merova B, Ondra P: GC/MS determination of ibotenic acid and muscimol in the urine of patients intoxicated with Amanita pantherina. Int J Legal Med. 2012 Jul;126(4):519-24. doi: 10.1007/s00414-011-0599-9. Epub 2011 Jul 13. [PubMed:21751026 ]
Avery L, Horvitz HR: Effects of starvation and neuroactive drugs on feeding in Caenorhabditis elegans. J Exp Zool. 1990 Mar;253(3):263-70. doi: 10.1002/jez.1402530305. [PubMed:2181052 ]

Showing NP-Card for Muscimol (NP0021691)

MOL for NP0021691 (Muscimol)

3D MOL for NP0021691 (Muscimol)

3D SDF for NP0021691 (Muscimol)

3D-SDF for NP0021691 (Muscimol)

PDB for NP0021691 (Muscimol)

3D PDB for NP0021691 (Muscimol)

SMILES for NP0021691 (Muscimol)

INCHI for NP0021691 (Muscimol)

Structure for NP0021691 (Muscimol)

3D Structure for NP0021691 (Muscimol)