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Showing NP-Card for Arsenobetaine (NP0073375)

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Record Information
Version2.0
Created at2022-04-28 18:38:17 UTC
Updated at2022-04-28 18:38:17 UTC
NP-MRD IDNP0073375
Secondary Accession NumbersNone
Natural Product Identification
Common NameArsenobetaine
DescriptionArsenobetaine belongs to the class of organic compounds known as tetraorganoarsonium salts. These are organoarsenic compounds, where the arsenic atom is tetrasubstituted by organic groups. They have the general structure R4[As+]X-, X=any atom but H. Arsenobetaine is a moderately acidic compound (based on its pKa). Outside of the human body, Arsenobetaine has been detected, but not quantified in, crustaceans. This could make arsenobetaine a potential biomarker for the consumption of these foods. The; Besides several other arsenic compounds, such as dimethylarsine and trimethylarsine, arsenobetaine is a common substance in the marine biological systems for arsenic detoxification. Arsenobetaine is a potentially toxic compound. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Arsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenobetaine is found in Abudefduf vaigiensis, Buccinum striatissimum, Panulirus cygnus, Sergia lucens, Sparassis crispa and Thunnus alalunga. Found in algae, lobsters, sharks, etc.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0073375 (Arsenobetaine)


  Mrv0541 09051416572D          

  8  7  0  0  0  0            999 V2000
    0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 As  0  3  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
Download

3D MOL for NP0073375 (Arsenobetaine)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.4721   -1.1531   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    0.0763   -0.0586 As  0  0  0  0  0  4  0  0  0  0  0  0
   -1.1553    1.8649   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.5712    1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204    0.1402   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.4401   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0757   -1.4577   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8301    0.2176    1.0681 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8215   -0.7183   -2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8689   -2.0901   -1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.4092   -0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.5649   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247    2.3064    1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.8016   -0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.6649    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.1912    2.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -1.5589    1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6804    1.2121   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930   -0.3118   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
M  CHG  2   2   1   8  -1
M  END
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3D SDF for NP0073375 (Arsenobetaine)


  Mrv0541 09051416572D          

  8  7  0  0  0  0            999 V2000
    0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 As  0  3  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
> <DATABASE_ID>
NP0073375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[As+](C)(C)CC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3

> <INCHI_KEY>
SPTHHTGLGVZZRH-UHFFFAOYSA-N

> <FORMULA>
C5H11AsO2

> <MOLECULAR_WEIGHT>
178.0612

> <EXACT_MASS>
177.997501013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.904754534374948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(trimethylarsaniumyl)acetate

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
0.9413000000000002

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8996134720700346

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
39.2657

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arsenobetaine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0073375 (Arsenobetaine)

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PDB for NP0073375 (Arsenobetaine)
HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       0.770   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206   1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6 As   UNK     0       1.540   2.667   0.000  0.00  0.00          As+1
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7    8                                                  
CONECT    6    1    2    3    4                                             
CONECT    7    5                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0073375 (Arsenobetaine)
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SMILES for NP0073375 (Arsenobetaine)
C[As+](C)(C)CC([O-])=O
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INCHI for NP0073375 (Arsenobetaine)
InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
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View in JSmol
Synonyms
ValueSource
(Carboxymethyl)trimethylarsonium hydroxide inner saltHMDB
(Carboxymethyl)trimethylarsonium hydroxide inner salt, 9ciHMDB
2-(Trimethylarsonio)acetateHMDB
Arsenobetaine monohydrateHMDB
Arsonium, (carboxymethyl)trimethyl-, hydroxide, inner saltHMDB
Chemical FormulaC5H11AsO2
Average Mass178.0612 Da
Monoisotopic Mass177.99750 Da
IUPAC Name2-(trimethylarsaniumyl)acetate
Traditional Namearsenobetaine
CAS Registry NumberNot Available
SMILES
C[As+](C)(C)CC([O-])=O
InChI Identifier
InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChI KeySPTHHTGLGVZZRH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abudefduf vaigiensisLOTUS Database
Buccinum striatissimumLOTUS Database
Panulirus cygnusLOTUS Database
Sergia lucensLOTUS Database
Sparassis crispaFungi
Thunnus alalungaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetraorganoarsonium salts. These are organoarsenic compounds, where the arsenic atom is tetrasubstituted by organic groups. They have the general structure R4[As+]X-, X=any atom but H.
KingdomOrganic compounds  
Super ClassOrganometallic compounds  
ClassOrganometalloid compounds  
Sub ClassOrganoarsenic compounds  
Direct ParentTetraorganoarsonium salts  
Alternative Parents
Substituents
  • Tetraorganoarsonium salt
    • 

  • Carboxylic acid salt
    • 

  • Oxygen-containing organoarsenic compound
    • 

  • Organic metalloid salt
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.84ALOGPS
logP0.94ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.27 m³·mol⁻¹ChemAxon
Polarizability13.9 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033206  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011219  
KNApSAcK IDC00033652  
Chemspider ID43109  
KEGG Compound IDC19331  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArsenobetaine  
METLIN IDNot Available
PubChem Compound47364  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available