MiMeDB: Showing metabocard for atropine (MMDBc0055739)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:03:50 UTC

Update Date

2022-12-15 22:52:22 UTC

Metabolite ID

MMDBc0055739

Metabolite Identification

Common Name

atropine

Description

atropinium, also known as atropinium cation, belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. atropinium 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. Based on a literature review a significant number of articles have been published on atropinium.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222032D          

 25 27  0  0  0  0            999 V2000
    7.3590    3.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7962    3.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087    3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756    3.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1189    2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804    4.1192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9073    2.5138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4373    2.7354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2939    2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6445    3.4324    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.5794    1.0854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083    3.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228    2.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7372    4.9075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4684    1.9090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064    1.9109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    1.9104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 20 17  2  0  0  0  0
 15 21  1  6  0  0  0
 21 17  1  0  0  0  0
 13 22  1  1  0  0  0
 14 23  1  1  0  0  0
 15 24  1  1  0  0  0
 25 16  1  0  0  0  0
M  CHG  1  18   1
M  END


  Mrv1652306172222032D          

 25 27  0  0  0  0            999 V2000
    7.3590    3.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7962    3.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087    3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756    3.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1189    2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804    4.1192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9073    2.5138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4373    2.7354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2939    2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083    2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6445    3.4324    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.5794    1.0854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083    3.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228    2.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7372    4.9075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4684    1.9090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064    1.9109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    1.9104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 20 17  2  0  0  0  0
 15 21  1  6  0  0  0
 21 17  1  0  0  0  0
 13 22  1  1  0  0  0
 14 23  1  1  0  0  0
 15 24  1  1  0  0  0
 25 16  1  0  0  0  0
M  CHG  1  18   1
M  END
> <DATABASE_ID>
MMDBc0055739

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CO)(C(=O)O[C@]1([H])C[C@]2([H])CC[C@]([H])(C1)[NH+]2C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/p+1/t13-,14+,15+,16?

> <INCHI_KEY>
RKUNBYITZUJHSG-SPUOUPEWSA-O

> <FORMULA>
C17H24NO3

> <MOLECULAR_WEIGHT>
290.382

> <EXACT_MASS>
290.175070057

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.16345347523645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

> <JCHEM_LOGP>
1.571241016666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145740617562414

> <JCHEM_PKA_STRONGEST_BASIC>
9.385561870758496

> <JCHEM_POLAR_SURFACE_AREA>
50.97

> <JCHEM_REFRACTIVITY>
91.83330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      13.737   7.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.148   6.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.148   5.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.481   7.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.481   4.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.815   6.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.686   7.460   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.456   6.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.035   6.642   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.422   4.238   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.149   2.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.815   5.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.163   7.689   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.894   4.692   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.150   5.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.149   4.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.482   5.106   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      12.403   6.407   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0       4.815   2.026   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.482   6.646   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.816   4.336   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      10.709   9.161   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      13.941   3.564   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      10.092   3.567   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.815   3.566   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   13   15                                                       
CONECT   10   14   15                                                       
CONECT   11   16   19                                                       
CONECT   12    5    6   16                                                  
CONECT   13    7    9   18   22                                             
CONECT   14    8   10   18   23                                             
CONECT   15    9   10   21   24                                             
CONECT   16   11   12   17   25                                             
CONECT   17   16   20   21                                                  
CONECT   18    1   13   14                                                  
CONECT   19   11                                                            
CONECT   20   17                                                            
CONECT   21   15   17                                                       
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Synonyms

Value	Source
Atropine	ChEBI
Atropinium cation	ChEBI
Atropinium(1+)	ChEBI

Molecular Formula

C₁₇H₂₄NO₃

Average Mass

290.382

Monoisotopic Mass

290.175070057

IUPAC Name

(1R,3S,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

Traditional Name

(1R,3S,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octan-8-ium

CAS Registry Number

Not Available

SMILES

[H]C(CO)(C(=O)O[C@]1([H])C[C@]2([H])CC[C@]([H])(C1)[NH+]2C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/p+1/t13-,14+,15+,16?

InChI Key

RKUNBYITZUJHSG-SPUOUPEWSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ammonium ion (CHEBI:57858 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.57	ChemAxon
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.83 m³·mol⁻¹	ChemAxon
Polarizability	32.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10246419

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

57858

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for atropine (MMDBc0055739)

MOL for #<Metabolite:0x0000556b69119c50>

3D MOL for #<Metabolite:0x0000556b69119c50>

3D SDF for #<Metabolite:0x0000556b69119c50>

3D-SDF for #<Metabolite:0x0000556b69119c50>

PDB for #<Metabolite:0x0000556b69119c50>

3D PDB for #<Metabolite:0x0000556b69119c50>

SMILES for #<Metabolite:0x0000556b69119c50>

INCHI for #<Metabolite:0x0000556b69119c50>

Structure for #<Metabolite:0x0000556b69119c50>

3D Structure for #<Metabolite:0x0000556b69119c50>