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Showing metabocard for Acetylcholine (HMDB0000895)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:27 UTC
HMDB IDHMDB0000895
Secondary Accession Numbers
  • HMDB00895
Metabolite Identification
Common NameAcetylcholine
DescriptionAcetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID:17284361 , 17011181 , 15556286 ). Acetylcholine has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID:24621061 ).
Structure
Data?1582752163
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000895 (Acetylcholine)


  Mrv1652305271900012D          

 10  9  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  CHG  1   7   1
M  END
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3D MOL for HMDB0000895 (Acetylcholine)

HMDB0000895
     RDKit          3D
Acetylcholine
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.2649    0.5271    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    0.4869   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    1.5873   -0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -0.6709   -0.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6928   -0.7608   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.0285    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -0.0720    0.2498 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1271    0.5974    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -1.4324    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    0.5588   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707    0.6942    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312    1.3328   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820   -0.4400   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5316   -0.2471   -1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3598   -1.8130   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.4677    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892    1.0452    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325    1.6740    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2116    0.3549    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.2003    2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -1.7734   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757   -2.0943    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055   -1.3680    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.2197   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9287    1.0062   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    1.3226   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  CHG  1   7   1
M  END
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3D SDF for HMDB0000895 (Acetylcholine)


  Mrv1652305271900012D          

 10  9  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
HMDB0000895

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1

> <INCHI_KEY>
OIPILFWXSMYKGL-UHFFFAOYSA-N

> <FORMULA>
C7H16NO2

> <MOLECULAR_WEIGHT>
146.2074

> <EXACT_MASS>
146.118103761

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.691995989128777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(acetyloxy)ethyl]trimethylazanium

> <ALOGPS_LOGP>
-2.91

> <JCHEM_LOGP>
-4.221143752471746

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0082411552327235

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
51.3455

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylcholine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0000895 (Acetylcholine)

HMDB0000895
     RDKit          3D
Acetylcholine
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.2649    0.5271    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    0.4869   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    1.5873   -0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -0.6709   -0.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6928   -0.7608   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.0285    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -0.0720    0.2498 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1271    0.5974    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -1.4324    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    0.5588   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707    0.6942    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312    1.3328   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820   -0.4400   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5316   -0.2471   -1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3598   -1.8130   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.4677    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892    1.0452    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325    1.6740    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2116    0.3549    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.2003    2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682   -1.7734   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757   -2.0943    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055   -1.3680    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.2197   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9287    1.0062   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    1.3226   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  CHG  1   7   1
M  END
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PDB for HMDB0000895 (Acetylcholine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620  -1.127   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.954  -3.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       9.955  -2.667   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      11.288  -1.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.725  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.185  -1.334   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0000895 (Acetylcholine)

COMPND    HMDB0000895
HETATM    1  C1  UNL     1       4.265   0.527   0.040  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.808   0.487  -0.252  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.236   1.587  -0.450  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.075  -0.671  -0.314  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.693  -0.761  -0.585  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.080  -0.029   0.453  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.511  -0.072   0.250  1.00  0.00           N1+
HETATM    8  C5  UNL     1      -2.127   0.597   1.384  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.020  -1.432   0.235  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.921   0.559  -0.973  1.00  0.00           C  
HETATM   11  H1  UNL     1       4.471   0.694   1.119  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.731   1.333  -0.566  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.682  -0.440  -0.313  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.532  -0.247  -1.557  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.360  -1.813  -0.600  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.106  -0.468   1.472  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.189   1.045   0.477  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.933   1.674   1.324  1.00  0.00           H  
HETATM   19  H9  UNL     1      -3.212   0.355   1.364  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.638   0.200   2.297  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.968  -1.773  -0.819  1.00  0.00           H  
HETATM   22  H12 UNL     1      -1.476  -2.094   0.931  1.00  0.00           H  
HETATM   23  H13 UNL     1      -3.105  -1.368   0.488  1.00  0.00           H  
HETATM   24  H14 UNL     1      -1.999  -0.220  -1.783  1.00  0.00           H  
HETATM   25  H15 UNL     1      -2.929   1.006  -0.826  1.00  0.00           H  
HETATM   26  H16 UNL     1      -1.227   1.323  -1.342  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   14   15
CONECT    6    7   16   17
CONECT    7    8    9   10
CONECT    8   18   19   20
CONECT    9   21   22   23
CONECT   10   24   25   26
END
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SMILES for HMDB0000895 (Acetylcholine)

CC(=O)OCC[N+](C)(C)C
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INCHI for HMDB0000895 (Acetylcholine)

InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
AChChEBI
AzetylcholinChEBI
Choline acetateChEBI
O-AcetylcholineChEBI
Choline acetic acidGenerator
Acetylcholine iodideHMDB
Acetylcholine perchlorateHMDB
Acetylcholine sulfate (1:1)HMDB
BromoacetylcholineHMDB
Cusi, acetilcolinaHMDB
Iodide, acetylcholineHMDB
2-(Acetyloxy)-N,N,N-trimethylethanaminiumHMDB
Acetilcolina cusiHMDB
Acetylcholine fluorideHMDB
Acetylcholine L tartrateHMDB
Acetylcholine picrateHMDB
ChloroacetylcholineHMDB
MiocholHMDB
Perchlorate, acetylcholineHMDB
Acetylcholine L-tartrateHMDB
Acetylcholine picrate (1:1)HMDB
Hydroxide, acetylcholineHMDB
Acetylcholine bromideHMDB
Acetylcholine chlorideHMDB
Acetylcholine hydroxideHMDB
Bromide, acetylcholineHMDB
Fluoride, acetylcholineHMDB
L-Tartrate, acetylcholineHMDB
Acetyl choline ionHMDB
Acetylcholine cationHMDB
Acetylcholinium: acetyl-cholineHMDB
Choline acetate (ester)HMDB
Bournonville brand OF acetylcholine chlorideHMDB
Iolab brand OF acetylcholine chlorideHMDB
Alcon brand OF acetylcholine chlorideHMDB
Ciba vision brand OF acetylcholine chlorideHMDB
AcetylcholineMeSH, HMDB
Chemical FormulaC7H16NO2
Average Molecular Weight146.2074
Monoisotopic Molecular Weight146.118103761
IUPAC Name[2-(acetyloxy)ethyl]trimethylazanium
Traditional Nameacetylcholine
CAS Registry Number51-84-3
SMILES
CC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChI KeyOIPILFWXSMYKGL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos129.67730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-2.9ALOGPS
logP-4.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.35 m³·mol⁻¹ChemAxon
Polarizability16.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+131.78232859911
AllCCS[M-H]-143.71532859911
DeepCCS[M+H]+128.36230932474
DeepCCS[M-H]-125.69530932474
DeepCCS[M-2H]-161.94330932474
DeepCCS[M+Na]+136.54430932474
AllCCS[M+H]+131.832859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+135.332859911
AllCCS[M+Na]+136.332859911
AllCCS[M-H]-143.732859911
AllCCS[M+Na-2H]-145.932859911
AllCCS[M+HCOO]-148.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetylcholineCC(=O)OCC[N+](C)(C)C1349.2Standard polar33892256
AcetylcholineCC(=O)OCC[N+](C)(C)C840.7Standard non polar33892256
AcetylcholineCC(=O)OCC[N+](C)(C)C998.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetylcholine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9100000000-bf8d3f373f038db1a3102017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000j-9600000000-ec60451904fda7dde5562012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000l-9000000000-2ea4c086c3ab458a1d7c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-98d5a70eed75a0945da42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0002-1900000000-2da10e016ac539b6e9812012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-000i-9000000000-7efaaa08a6c43d8163582012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-000i-9000000000-eb7d66198d7674cbbd2a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-000l-9000000000-41b87d773c58129802e92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0006-9000000000-9e8e66250f2cf34a20462012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-0900000000-f7fe18f2371596dc73332012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-000j-9800000000-b0f987ebcb0179a2c5ab2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QTOF , positive-QTOFsplash10-000i-9000000000-1be58612df9c1eef12822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ , positive-QTOFsplash10-0002-1900000000-2da10e016ac539b6e9812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ , positive-QTOFsplash10-000i-9000000000-7efaaa08a6c43d8163582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ , positive-QTOFsplash10-000i-9000000000-eb7d66198d7674cbbd2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ , positive-QTOFsplash10-000l-9000000000-41b87d773c58129802e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-9ac44e29bdfbddf1b90d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-f7fe18f2371596dc73332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine LC-ESI-QTOF , positive-QTOFsplash10-000j-9800000000-b0f987ebcb0179a2c5ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetylcholine , positive-QTOFsplash10-000j-9400000000-8a3a0b77e93715b85ed42017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.034 +/- 0.009 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified8.56 +/- 5.19 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.016 +/- 0.007 uMAdult (>18 years old)Not SpecifiedVascular dementia details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. [PubMed:15361288 ]
Multi-infarct dementia
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. [PubMed:15361288 ]
Associated OMIM IDs
DrugBank IDDB03128
Phenol Explorer Compound IDNot Available
FooDB IDFDB012191
KNApSAcK IDC00054040
Chemspider ID182
KEGG Compound IDC01996
BioCyc IDACETYLCHOLINE
BiGG ID38868
Wikipedia LinkAcetylcholine
METLIN ID57
PubChem Compound187
PDB IDNot Available
ChEBI ID15355
Food Biomarker OntologyNot Available
VMH IDACH
MarkerDB IDMDB00000277
Good Scents IDNot Available
References
Synthesis ReferenceSzutowicz, Andrzej. Acetylcholine synthesis in synaptosomes. Postepy Biochemii (1979), 25(1), 59-84.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nguyen VT, Ndoye A, Hall LL, Zia S, Arredondo J, Chernyavsky AI, Kist DA, Zelickson BD, Lawry MA, Grando SA: Programmed cell death of keratinocytes culminates in apoptotic secretion of a humectant upon secretagogue action of acetylcholine. J Cell Sci. 2001 Mar;114(Pt 6):1189-204. [PubMed:11228162 ]
  2. Chia S, Megson IL, Ludlam CA, Fox KA, Newby DE: Preserved endothelial vasomotion and fibrinolytic function in patients with acute stent thrombosis or in-stent restenosis. Thromb Res. 2003;111(6):343-9. [PubMed:14698651 ]
  3. Grando SA, Kist DA, Qi M, Dahl MV: Human keratinocytes synthesize, secrete, and degrade acetylcholine. J Invest Dermatol. 1993 Jul;101(1):32-6. [PubMed:8331294 ]
  4. Beilin B, Bessler H, Papismedov L, Weinstock M, Shavit Y: Continuous physostigmine combined with morphine-based patient-controlled analgesia in the postoperative period. Acta Anaesthesiol Scand. 2005 Jan;49(1):78-84. [PubMed:15675987 ]
  5. Tao J, Jin YF, Yang Z, Wang LC, Gao XR, Lui L, Ma H: Reduced arterial elasticity is associated with endothelial dysfunction in persons of advancing age: comparative study of noninvasive pulse wave analysis and laser Doppler blood flow measurement. Am J Hypertens. 2004 Aug;17(8):654-9. [PubMed:15288882 ]
  6. Jiang JL, Jiang DJ, Tang YH, Li NS, Deng HW, Li YJ: Effect of simvastatin on endothelium-dependent vaso-relaxation and endogenous nitric oxide synthase inhibitor. Acta Pharmacol Sin. 2004 Jul;25(7):893-901. [PubMed:15210062 ]
  7. Haug KH, Bogen IL, Osmundsen H, Walaas I, Fonnum F: Effects on cholinergic markers in rat brain and blood after short and prolonged administration of donepezil. Neurochem Res. 2005 Dec;30(12):1511-20. [PubMed:16362770 ]
  8. Katoh H, Shimada T, Inoue S, Takahashi N, Shimizu H, Ohta Y, Nakamura K, Murakami Y, Ishibashi Y, Matsumori A: Reduced high serum hepatocyte growth factor levels after successful cardioversion in patients with atrial fibrillation. Clin Exp Pharmacol Physiol. 2004 Mar;31(3):145-51. [PubMed:15008956 ]
  9. Main C, Blennerhassett P, Collins SM: Human recombinant interleukin 1 beta suppresses acetylcholine release from rat myenteric plexus. Gastroenterology. 1993 Jun;104(6):1648-54. [PubMed:8500722 ]
  10. Ikarashi Y, Harigaya Y, Tomidokoro Y, Kanai M, Ikeda M, Matsubara E, Kawarabayashi T, Kuribara H, Younkin SG, Maruyama Y, Shoji M: Decreased level of brain acetylcholine and memory disturbance in APPsw mice. Neurobiol Aging. 2004 Apr;25(4):483-90. [PubMed:15013569 ]
  11. Katz SD, Krum H: Acetylcholine-mediated vasodilation in the forearm circulation of patients with heart failure: indirect evidence for the role of endothelium-derived hyperpolarizing factor. Am J Cardiol. 2001 May 1;87(9):1089-92. [PubMed:11348607 ]
  12. Hanna ST, Cao K, Wang R: Interaction of acetylcholine with Kir6.1 channels heterologously expressed in human embryonic kidney cells. Eur J Pharmacol. 2005 May 16;515(1-3):34-42. [PubMed:15894309 ]
  13. Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK: Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. Epub 2005 Nov 7. [PubMed:16275899 ]
  14. Shirahata M, Balbir A, Otsubo T, Fitzgerald RS: Role of acetylcholine in neurotransmission of the carotid body. Respir Physiol Neurobiol. 2007 Jul 1;157(1):93-105. Epub 2007 Jan 11. [PubMed:17284361 ]
  15. Hasselmo ME: The role of acetylcholine in learning and memory. Curr Opin Neurobiol. 2006 Dec;16(6):710-5. Epub 2006 Sep 29. [PubMed:17011181 ]
  16. Beane M, Marrocco RT: Norepinephrine and acetylcholine mediation of the components of reflexive attention: implications for attention deficit disorders. Prog Neurobiol. 2004 Oct;74(3):167-81. [PubMed:15556286 ]
  17. Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. [PubMed:24621061 ]
  18. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Choline O-acetyltransferase
General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name:
CHAT
Uniprot ID:
P28329
Molecular weight:
70425.285
Reactions
Acetyl-CoA + Choline → Coenzyme A + Acetylcholinedetails
Enzyme Details
2. Acetylcholinesterase
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
Reactions
Acetylcholine + Water → Choline + Acetic aciddetails
Enzyme Details
3. Cholinesterase
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575