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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:41:39 UTC

Update Date

2022-09-22 18:34:39 UTC

HMDB ID

HMDB0341206

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+/-)-Anatoxin A

Description

Anatoxin a belongs to the class of organic compounds known as anatoxins. These are organic compounds containing or derived from anatoxin, homoanatoxin or other analogues. Anatoxins constitute a class of potent neurotoxic alkaloids. Based on a literature review very few articles have been published on Anatoxin a.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       3.393   6.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.831   1.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.742   0.024   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.831   2.653   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.113   1.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.113   2.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.331   5.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.202   0.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.742   3.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.202   3.742   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.666   1.883   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.858   5.365   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    1    9   12                                                  
CONECT    8    3    5   11                                                  
CONECT    9    4    7   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11    8   10                                                       
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0248385
HETATM    1  C1  UNL     1       3.428   0.446   0.522  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.352  -0.486   0.129  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.609  -1.710   0.083  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.010  -0.056  -0.207  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.775   1.240  -0.148  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.519   1.986  -0.356  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.621   1.170   0.223  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.982  -0.056  -0.541  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.116  -1.193   0.465  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.701  -1.657   0.612  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.046  -1.114  -0.581  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.983  -0.535  -1.442  1.00  0.00           N  
HETATM   13  H1  UNL     1       4.404  -0.012   0.629  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.519   1.191  -0.320  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.098   1.035   1.397  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.634   1.853   0.084  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.642   2.238  -1.413  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.429   2.917   0.221  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.532   1.827   0.278  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.356   0.958   1.291  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.947   0.045  -1.093  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.812  -1.968   0.147  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.427  -0.771   1.453  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.731  -2.785   0.601  1.00  0.00           H  
HETATM   25  H13 UNL     1      -0.227  -1.376   1.565  1.00  0.00           H  
HETATM   26  H14 UNL     1       0.541  -1.976  -1.080  1.00  0.00           H  
HETATM   27  H15 UNL     1      -1.390  -1.210  -2.098  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5    5   11
CONECT    5    6   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   12   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   12   26
CONECT   12   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Anatoxin	ChEMBL
Anatoxin I	MeSH
Anatoxin-a	MeSH
ANTX-a	MeSH

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

1-{9-azabicyclo[4.2.1]non-2-en-2-yl}ethan-1-one

Traditional Name

anatoxin-a

CAS Registry Number

Not Available

SMILES

CC(=O)C1=CCCC2CCC1N2

InChI Identifier

InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3

InChI Key

SGNXVBOIDPPRJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anatoxins. These are organic compounds containing or derived from anatoxin, homoanatoxin or other analogues. Anatoxins constitute a class of potent neurotoxic alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Anatoxins

Sub Class

Not Available

Direct Parent

Anatoxins

Alternative Parents

Substituents

Anatoxin skeleton
Azepine
Beta-aminoketone
Pyrrolidine
Ketone
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tropane alkaloid (CHEBI:2706 )
Tropane alkaloids (C10841 )
Anatoxins (C10841 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.25	ALOGPS
logP	1.19	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.83 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	142.05	30932474
DeepCCS	[M-H]-	139.585	30932474
DeepCCS	[M-2H]-	175.185	30932474
DeepCCS	[M+Na]+	150.221	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1132.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	263.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	276.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	365.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	712.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	265.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	767.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	617.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	350.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	152.5 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethanone, 1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-, (1R)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-5900000000-ba20b4a810e4d42d829b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethanone, 1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-, (1R)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 10V, Positive-QTOF	splash10-014i-0900000000-102ee8cf61f9a3fca40f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 20V, Positive-QTOF	splash10-014i-1900000000-62ceaf7d188b3e837a0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 40V, Positive-QTOF	splash10-0frx-9100000000-86534e8472925e41161d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 10V, Negative-QTOF	splash10-03di-0900000000-61d9204215a77bd1ba8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 20V, Negative-QTOF	splash10-03k9-0900000000-0441fd550dfe2b4045ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 40V, Negative-QTOF	splash10-00dl-7900000000-d66fc910a434d2965dae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 10V, Positive-QTOF	splash10-014i-0900000000-a8baa4b5218fe504eb78	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 20V, Positive-QTOF	splash10-014i-1900000000-1056846b3b1bb9f81930	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 40V, Positive-QTOF	splash10-00di-4900000000-3a6f2ccf799ae8ef3163	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 10V, Negative-QTOF	splash10-03di-0900000000-5a67776f4d9f6897ce74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 20V, Negative-QTOF	splash10-03di-0900000000-86ab77a5296b6cbb848b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Anatoxin A 40V, Negative-QTOF	splash10-03kd-4900000000-29dfc9ff3d3d7c9d9b9e	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002273

Chemspider ID

381822

KEGG Compound ID

C10841

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

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for (+/-)-Anatoxin A (HMDB0341206)

MOL for HMDB0341206 ((+/-)-Anatoxin A)

3D MOL for HMDB0341206 ((+/-)-Anatoxin A)

3D SDF for HMDB0341206 ((+/-)-Anatoxin A)

3D-SDF for HMDB0341206 ((+/-)-Anatoxin A)

PDB for HMDB0341206 ((+/-)-Anatoxin A)

3D PDB for HMDB0341206 ((+/-)-Anatoxin A)

SMILES for HMDB0341206 ((+/-)-Anatoxin A)

INCHI for HMDB0341206 ((+/-)-Anatoxin A)

Structure for HMDB0341206 ((+/-)-Anatoxin A)

3D Structure for HMDB0341206 ((+/-)-Anatoxin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra