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Showing NP-Card for cacodylic acid (NP0002919)

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Record Information
Version1.0
Created at2020-11-23 19:43:37 UTC
Updated at2021-08-12 19:52:31 UTC
NP-MRD IDNP0002919
Secondary Accession NumbersNone
Natural Product Identification
Common Namecacodylic acid
Provided ByBMRBBMRB logo
DescriptionDimethylarsinic acid, also known as dimethylarsinate or [as(CH3)2O(OH)], belongs to the class of organic compounds known as pentaorganoarsanes. These are organoarsenic compounds containing an arsenic compound that is pentasubstituted by only organic groups. In humans, dimethylarsinic acid is involved in the arsenate detoxification pathway. Dimethylarsinic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Dimethylarsinic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. It was first documented in 2001 (PMID: 11379771). Based on a literature review a small amount of articles have been published on Dimethylarsinic acid (PMID: 17984079) (PMID: 21342701) (PMID: 11549254) (PMID: 21457993).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002919 (cacodylic acid)


     RDKit          2D

 12 11  0  0  0  0  0  0  0  0999 V2000
    1.3239   -0.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501   -0.1745    0.0000 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.6240    0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -1.6484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283    1.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.9761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455   -1.9268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -0.7313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9024   -1.3700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    1.5778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979    0.3823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    1.9642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  1
  1  6  1  6
  1  7  1  0
  1  8  1  0
  3  9  1  1
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
Download

3D MOL for NP0002919 (cacodylic acid)

NP0002919
     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6570   -0.3419   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150    0.4888    0.3227 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.4574   -0.7982   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    0.6639    1.9597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3662    2.0639   -0.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077   -1.0497   -1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.0005    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236    0.3727   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.4900    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.7640    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663   -0.8818   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    2.7368    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
Download

3D SDF for NP0002919 (cacodylic acid)


     RDKit          2D

 12 11  0  0  0  0  0  0  0  0999 V2000
    1.3239   -0.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501   -0.1745    0.0000 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.6240    0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -1.6484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283    1.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.9761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455   -1.9268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -0.7313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9024   -1.3700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    1.5778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979    0.3823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    1.9642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  1
  1  6  1  6
  1  7  1  0
  1  8  1  0
  3  9  1  1
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
> <DATABASE_ID>
NP0002919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[As](C)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

> <INCHI_KEY>
OGGXGZAMXPVRFZ-UHFFFAOYSA-N

> <FORMULA>
C2H7AsO2

> <MOLECULAR_WEIGHT>
137.9974

> <EXACT_MASS>
137.966200885

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.178944868338649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethylarsinic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-0.32920000000000016

> <ALOGPS_LOGS>
0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.222333786503422

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
15.898900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ansar

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002919 (cacodylic acid)

NP0002919
     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6570   -0.3419   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150    0.4888    0.3227 As  0  0  0  0  0  5  0  0  0  0  0  0
   -1.4574   -0.7982   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    0.6639    1.9597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3662    2.0639   -0.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077   -1.0497   -1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.0005    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236    0.3727   -0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.4900    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.7640    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663   -0.8818   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    2.7368    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
M  END
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PDB for NP0002919 (cacodylic acid)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2 As   UNK     0       1.540   0.000   0.000  0.00  0.00          As+0
HETATM    3  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for NP0002919 (cacodylic acid)

COMPND    NP0002919
HETATM    1  C1  UNL     1       1.657  -0.342  -0.262  1.00  0.00           C  
HETATM    2 AS1  UNL     1      -0.015   0.489   0.323  1.00  0.00          AS  
HETATM    3  C2  UNL     1      -1.457  -0.798  -0.118  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.022   0.664   1.960  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.366   2.064  -0.490  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.508  -1.050  -1.120  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.003  -1.001   0.581  1.00  0.00           H  
HETATM    8  H3  UNL     1       2.424   0.373  -0.572  1.00  0.00           H  
HETATM    9  H4  UNL     1      -2.362  -0.490   0.418  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.129  -1.764   0.314  1.00  0.00           H  
HETATM   11  H6  UNL     1      -1.566  -0.882  -1.206  1.00  0.00           H  
HETATM   12  H7  UNL     1      -0.674   2.737   0.173  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    4    5
CONECT    3    9   10   11
CONECT    5   12
END
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SMILES for NP0002919 (cacodylic acid)

C[As](C)(O)=O
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INCHI for NP0002919 (cacodylic acid)

InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
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Synonyms
ValueSource
[As(CH3)2O(OH)]ChEBI
CACODYLIC ACIDChEBI
DimethylarsinateChEBI
KakodylsaeureChEBI
Me2as(=o)OHChEBI
CACODYLateGenerator
Dimethylarsinic acidGenerator
Acid, dimethylarsinicMeSH, HMDB
Acid, cacodylicMeSH, HMDB
As,As-Dimethylarsinic acidHMDB
Dimethylarsenic acidHMDB
Hydroxydimethylarsine oxideHMDB
Chemical FormulaC2H7AsO2
Average Mass137.9974 Da
Monoisotopic Mass137.96620 Da
IUPAC Namedimethylarsinic acid
Traditional Nameansar
CAS Registry NumberNot Available
SMILES
C[As](C)(O)=O
InChI Identifier
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
InChI KeyOGGXGZAMXPVRFZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Species Where Detected
Species NameSourceReference
Laccaria laccataKNApSAcK Database
Leucocoprinus badhamiiKNApSAcK Database
Volvariella volvaceaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentaorganoarsanes. These are organoarsenic compounds containing an arsenic compound that is pentasubstituted by only organic groups.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentPentaorganoarsanes
Alternative Parents
Substituents
  • Pentaorganoarsane
  • Alkylarsine oxide
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • 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
logP-0.48ALOGPS
logP-0.33ChemAxon
logS0.27ALOGPS
pKa (Strongest Acidic)6.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.9 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011625
DrugBank IDDB02994
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028327
KNApSAcK IDC00033777
Chemspider ID2418
KEGG Compound IDC07308
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCacodylic_acid
METLIN IDNot Available
PubChem Compound2513
PDB IDNot Available
ChEBI ID48765
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Yamanaka K, Mizol M, Kato K, Hasegawa A, Nakano M, Okada S: Oral administration of dimethylarsinic acid, a main metabolite of inorganic arsenic, in mice promotes skin tumorigenesis initiated by dimethylbenz(a)anthracene with or without ultraviolet B as a promoter. Biol Pharm Bull. 2001 May;24(5):510-4. doi: 10.1248/bpb.24.510. [PubMed:11379771 ]
  3. Maki T, Hirota W, Motojima H, Hasegawa H, Rahman MA: Influence of aggregated particles on biodegradation activities for dimethylarsinic acid (DMA) in Lake Kahokugata. Chemosphere. 2011 Jun;83(11):1486-92. doi: 10.1016/j.chemosphere.2011.01.059. Epub 2011 Feb 20. [PubMed:21342701 ]
  4. Yamanaka K, Takabayashi F, Mizoi M, An Y, Hasegawa A, Okada S: Oral exposure of dimethylarsinic acid, a main metabolite of inorganic arsenics, in mice leads to an increase in 8-Oxo-2'-deoxyguanosine level, specifically in the target organs for arsenic carcinogenesis. Biochem Biophys Res Commun. 2001 Sep 14;287(1):66-70. doi: 10.1006/bbrc.2001.5551. [PubMed:11549254 ]
  5. Mitchell W, Goldberg S, Al-Abadleh HA: In situ ATR-FTIR and surface complexation modeling studies on the adsorption of dimethylarsinic acid and p-arsanilic acid on iron-(oxyhydr)oxides. J Colloid Interface Sci. 2011 Jun 15;358(2):534-40. doi: 10.1016/j.jcis.2011.02.040. Epub 2011 Feb 24. [PubMed:21457993 ]