MiMeDB: Showing metabocard for Anhydrotetrodotoxin (MMDBc0024656)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 14:28:01 UTC

Update Date

2022-08-31 06:49:51 UTC

Metabolite ID

MMDBc0024656

Metabolite Identification

Common Name

Anhydrotetrodotoxin

Description

Anhydrotetrodotoxin, also known as 4,9-anhydro-TTX, belongs to the class of organic compounds known as tetrodotoxins. Tetrodotoxins are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety. Based on a literature review a significant number of articles have been published on Anhydrotetrodotoxin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152116282D          

 27 31  0  0  1  0            999 V2000
    2.4384    1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0755    0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    0.3716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3621   -1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -1.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4427   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8298    0.9404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1674   -0.5767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2172   -0.9551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1369    0.2498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -1.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674    0.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603    2.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412   -0.8090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -1.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -1.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    0.0644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -0.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -0.3940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    0.6077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    1.2524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1411    0.8797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504   -1.9069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972   -2.1084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  9  1  1  1  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10 14  1  6  0  0  0
 15  1  1  0  0  0  0
 16  3  1  0  0  0  0
  9 17  1  6  0  0  0
 11 18  1  1  0  0  0
 19  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20  4  1  0  0  0  0
 20 11  1  0  0  0  0
 21  5  1  0  0  0  0
 21 11  1  0  0  0  0
 22  2  1  0  0  0  0
  3 23  1  6  0  0  0
 24  4  1  0  0  0  0
  5 25  1  6  0  0  0
 26  6  1  0  0  0  0
  7 27  1  6  0  0  0
M  END


  Mrv1652305152116282D          

 27 31  0  0  1  0            999 V2000
    2.4384    1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0755    0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    0.3716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3621   -1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -1.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4427   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8298    0.9404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1674   -0.5767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2172   -0.9551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1369    0.2498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -1.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674    0.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603    2.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412   -0.8090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -1.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -1.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    0.0644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -0.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -0.3940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    0.6077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    1.2524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1411    0.8797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504   -1.9069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972   -2.1084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  9  1  1  1  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 10 14  1  6  0  0  0
 15  1  1  0  0  0  0
 16  3  1  0  0  0  0
  9 17  1  6  0  0  0
 11 18  1  1  0  0  0
 19  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20  4  1  0  0  0  0
 20 11  1  0  0  0  0
 21  5  1  0  0  0  0
 21 11  1  0  0  0  0
 22  2  1  0  0  0  0
  3 23  1  6  0  0  0
 24  4  1  0  0  0  0
  5 25  1  6  0  0  0
 26  6  1  0  0  0  0
  7 27  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0024656

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C12NC(=N)N[C@]34[C@]([H])(O1)[C@]1(O)OC([H])(C23[H])[C@@](O)(CO)[C@@]([H])(O1)[C@@]4([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N3O7/c12-8-13-6-2-4-9(17,1-15)5-3(16)10(2,14-8)7(19-6)11(18,20-4)21-5/h2-7,15-18H,1H2,(H3,12,13,14)/t2?,3-,4?,5+,6?,7+,9+,10-,11+/m1/s1

> <INCHI_KEY>
STNXQECXKDMLJK-NLWUVLGBSA-N

> <FORMULA>
C11H15N3O7

> <MOLECULAR_WEIGHT>
301.255

> <EXACT_MASS>
301.090999835

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.490141580442515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,11S,12S)-2-(hydroxymethyl)-7-imino-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1^{3,12}.0^{5,11}.0^{5,14}]pentadecane-2,4,12-triol

> <ALOGPS_LOGP>
-2.31

> <JCHEM_LOGP>
-4.147769365037784

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.060321168892726

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.162273377688646

> <JCHEM_PKA_STRONGEST_BASIC>
10.82934295688339

> <JCHEM_POLAR_SURFACE_AREA>
156.51999999999998

> <JCHEM_REFRACTIVITY>
71.7532

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,11S,12S)-2-(hydroxymethyl)-7-imino-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1^{3,12}.0^{5,11}.0^{5,14}]pentadecane-2,4,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       4.552   2.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.377  -0.441   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.098  -0.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.008   0.981   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.650   0.694   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.676  -2.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.903  -2.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.826  -0.366   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.416   1.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.179  -1.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.139  -1.783   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.122   0.466   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -0.793  -1.919   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.686   0.287   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.219   4.299   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.117  -1.510   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.518   3.007   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.731  -3.268   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.689  -3.359   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.362   0.120   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.412  -0.820   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -0.135  -0.735   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.708   1.134   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.279   2.338   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.863   1.642   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.094  -3.560   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.795  -3.936   0.000  0.00  0.00           H+0
CONECT    1    9   15                                                       
CONECT    2    4    6   10   22                                             
CONECT    3    5   10   16   23                                             
CONECT    4    2    9   20   24                                             
CONECT    5    3    9   21   25                                             
CONECT    6    2   13   19   26                                             
CONECT    7   10   11   19   27                                             
CONECT    8   12   13   14                                                  
CONECT    9    1    4    5   17                                             
CONECT   10    2    3    7   14                                             
CONECT   11    7   18   20   21                                             
CONECT   12    8                                                            
CONECT   13    6    8                                                       
CONECT   14    8   10                                                       
CONECT   15    1                                                            
CONECT   16    3                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19    6    7                                                       
CONECT   20    4   11                                                       
CONECT   21    5   11                                                       
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

Synonyms

Value	Source
4,9-Anhydro-TTX	MeSH
4,9-Anhydrotetrodotoxin	MeSH

Molecular Formula

C₁₁H₁₅N₃O₇

Average Mass

301.255

Monoisotopic Mass

301.090999835

IUPAC Name

(2S,3S,4S,5R,11S,12S)-2-(hydroxymethyl)-7-imino-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1^{3,12}.0^{5,11}.0^{5,14}]pentadecane-2,4,12-triol

Traditional Name

(2S,3S,4S,5R,11S,12S)-2-(hydroxymethyl)-7-imino-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1^{3,12}.0^{5,11}.0^{5,14}]pentadecane-2,4,12-triol

CAS Registry Number

Not Available

SMILES

[H]C12NC(=N)N[C@]34[C@]([H])(O1)[C@]1(O)OC([H])(C23[H])[C@@](O)(CO)[C@@]([H])(O1)[C@@]4([H])O

InChI Identifier

InChI=1S/C11H15N3O7/c12-8-13-6-2-4-9(17,1-15)5-3(16)10(2,14-8)7(19-6)11(18,20-4)21-5/h2-7,15-18H,1H2,(H3,12,13,14)/t2?,3-,4?,5+,6?,7+,9+,10-,11+/m1/s1

InChI Key

STNXQECXKDMLJK-NLWUVLGBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrodotoxins. Tetrodotoxins are compounds structurally characterized by the presence of the tetrodotoxin skeleton, which is based on 5,7-(epoxymethanooxy)quinazolin-10-olate moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Tetrodotoxins

Alternative Parents

Substituents

Tetrodotoxin-skeleton
Furopyran
Dioxepane
1,4-dioxepane
Pyran
Oxane
Monosaccharide
1,3-diazinane
Meta-dioxane
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Orthocarboxylic acid derivative
Guanidine
Oxacycle
Azacycle
Carboximidamide
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Imine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	107 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-4.1	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	10.16	ChemAxon
pKa (Strongest Basic)	10.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	156.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.75 m³·mol⁻¹	ChemAxon
Polarizability	26.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

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

Not Available

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 feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

21256822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107878

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Anhydrotetrodotoxin (MMDBc0024656)

MOL for #<Metabolite:0x00007fece2ffbde8>

3D MOL for #<Metabolite:0x00007fece2ffbde8>

3D SDF for #<Metabolite:0x00007fece2ffbde8>

3D-SDF for #<Metabolite:0x00007fece2ffbde8>

PDB for #<Metabolite:0x00007fece2ffbde8>

3D PDB for #<Metabolite:0x00007fece2ffbde8>

SMILES for #<Metabolite:0x00007fece2ffbde8>

INCHI for #<Metabolite:0x00007fece2ffbde8>

Structure for #<Metabolite:0x00007fece2ffbde8>

3D Structure for #<Metabolite:0x00007fece2ffbde8>