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Showing NP-Card for Nabam (NP0337983)

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Record Information
Version2.0
Created at2024-09-11 13:19:27 UTC
Updated at2024-09-11 13:19:28 UTC
NP-MRD IDNP0337983
Secondary Accession NumbersNone
Natural Product Identification
Common NameNabam
DescriptionNabam, also known as dithane a-40 or nabame, belongs to the class of organic compounds known as organic alkali metal salts. These are organic salts of an alkali metal. The alkali metal atom is usually in its ionic form. Nabam is a moderately acidic compound (based on its pKa). A fungicide, algicide and bactericide used on various crops including on cotton, capsicums, onions and rice crops, it is considered to be a carcinogen, so is not licensed for use within the European Union. A dithiocarbamate salt that is the disodium salt of ethylenebis(dithiocarbamic acid). It was first documented in 1958 (PMID: 17797593). Mixing nabam with zinc sulfate affords the fungicide zineb (PMID: 1161698) (PMID: 18966479) (PMID: 1904852) (PMID: 1929852).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337983 (Nabam)


  Mrv0541 02241219182D          

 12  9  0  0  0  0            999 V2000
   -0.2062    0.2472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    1.4847    0.0000 S   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9483    1.4847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505   -0.1653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0937   -1.4028    0.0000 S   0  5  0  0  0  0  0  0  0  0  0  0
   -2.3505   -0.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -1.4028    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -1.4847    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    3.0937    0.2472    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  CHG  4   3  -1   8  -1  11   1  12   1
M  END
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3D MOL for NP0337983 (Nabam)

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3D SDF for NP0337983 (Nabam)

  Mrv0541 02241219182D          

 12  9  0  0  0  0            999 V2000
   -0.2062    0.2472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    1.4847    0.0000 S   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9483    1.4847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505   -0.1653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0937   -1.4028    0.0000 S   0  5  0  0  0  0  0  0  0  0  0  0
   -2.3505   -0.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -1.4028    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -1.4847    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    3.0937    0.2472    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  CHG  4   3  -1   8  -1  11   1  12   1
M  END
> <DATABASE_ID>
NP0337983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Na+].[Na+].[S-]C(=S)NCCNC([S-])=S

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N2S4.2Na/c7-3(8)5-1-2-6-4(9)10;;/h1-2H2,(H2,5,7,8)(H2,6,9,10);;/q;2*+1/p-2

> <INCHI_KEY>
UQJQVUOTMVCFHX-UHFFFAOYSA-L

> <FORMULA>
C4H6N2Na2S4

> <MOLECULAR_WEIGHT>
256.343

> <EXACT_MASS>
255.920920312

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
20.938206291861682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
disodium ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
1.9688125666666665

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.3376019688627485

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7354489553978434

> <JCHEM_POLAR_SURFACE_AREA>
24.06

> <JCHEM_REFRACTIVITY>
60.75899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
disodium ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337983 (Nabam)
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PDB for NP0337983 (Nabam)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0      -0.385   0.461   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      -0.385   2.001   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       0.845   2.771   0.000  0.00  0.00           S-1
HETATM    4  N   UNK     0      -1.770   2.771   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -3.155   2.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.155   0.461   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -4.388  -0.309   0.000  0.00  0.00           N+0
HETATM    8  S   UNK     0      -5.775  -2.619   0.000  0.00  0.00           S-1
HETATM    9  C   UNK     0      -4.388  -1.849   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -3.155  -2.619   0.000  0.00  0.00           S+0
HETATM   11 Na   UNK     0       2.848  -2.771   0.000  0.00  0.00          Na+1
HETATM   12 Na   UNK     0       5.775   0.461   0.000  0.00  0.00          Na+1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    7    8   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   18    0
END

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3D PDB for NP0337983 (Nabam)
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SMILES for NP0337983 (Nabam)
[Na+].[Na+].[S-]C(=S)NCCNC([S-])=S
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INCHI for NP0337983 (Nabam)
InChI=1S/C4H8N2S4.2Na/c7-3(8)5-1-2-6-4(9)10;;/h1-2H2,(H2,5,7,8)(H2,6,9,10);;/q;2*+1/p-2
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Synonyms
ValueSource
1,2-Ethanediylbiscarbamodithioic acid disodium saltChEBI
Di-natrium-aethylenbisdithiocarbamatChEBI
Dinatrium-(N,n'-aethylen-bis(dithiocarbamat))ChEBI
Disodium ethylene-1,2-bisdithiocarbamateChEBI
Disodium ethylenebis(dithiocarbamate)ChEBI
Disodium N,n'-1,2-ethanediylbis(carbamodithioate)ChEBI
Disodium N,n'-ethane-1,2-diyldicarbamodithioateChEBI
Dithane a-40ChEBI
N,N'-ethylene bis(dithiocarbamate de sodium)ChEBI
NabameChEBI
ParzateChEBI
Sodium ethylenebis(dithiocarbamate)ChEBI
Spring-bakChEBI
1,2-Ethanediylbiscarbamodithioate disodium saltGenerator
Disodium ethylene-1,2-bisdithiocarbamic acidGenerator
Disodium ethylenebis(dithiocarbamic acid)Generator
Disodium N,n'-1,2-ethanediylbis(carbamodithioic acid)Generator
Disodium N,n'-ethane-1,2-diyldicarbamodithioic acidGenerator
N,N'-ethylene bis(dithiocarbamic acid de sodium)Generator
Parzic acidGenerator
Sodium ethylenebis(dithiocarbamic acid)Generator
AmobamHMDB
Carbamic acid, ethylenebis(dithio-, disodium saltHMDB
Carbamodithioic acid, 1,2-ethanediylbis-, disodiumHMDB
Carbamodithioic acid, 1,2-ethanediylbis-, disodium saltHMDB
Chem bamHMDB
Dinatrium-(N,n'-ethyleen-bis(dithiocarbamaat))HMDB
Disodium 1,2-ethanediylbis (carbamodithioate)HMDB
Disodium ethane-1,2-diylbis(dithiocarbamate)HMDB
Disodium ethylenebisdithiocarbamateHMDB
Dithane a40HMDB
Dithane D-14HMDB
Dithane D-14 (discontinued)HMDB
Dithiane D-14HMDB
DSEHMDB
Ebdc, disodium saltHMDB
Ethylen-bis-dithiokarbaman sodnyHMDB
Ethylenebis(dithiocarbamate) sodiumHMDB
Ethylenebis(dithiocarbamate), disodium saltHMDB
Ethylenebis(dithiocarbamic acid) disodium saltHMDB
Ethylenebisdithiocarbamate, disodiumHMDB
N,N'-etilen-bis(ditiocarbammato) di sodioHMDB
Nabam, ammonium saltHMDB
Nabam, bsi, isoHMDB
Nabam, calcium salt (1:1)HMDB
Nabam, diammonium saltHMDB
Nabam, dipotassium saltHMDB
Nabam, disodium saltHMDB
Nabam, iron saltHMDB
Nabam, potassium saltHMDB
Nabam, sodium saltHMDB
NabasanHMDB
Nafun ipoHMDB
Parzate liquidHMDB
X-SporHMDB
Chemical FormulaC4H6N2Na2S4
Average Mass256.3430 Da
Monoisotopic Mass255.92092 Da
IUPAC Namedisodium ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide
Traditional Namedisodium ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide
CAS Registry NumberNot Available
SMILES
[Na+].[Na+].[S-]C(=S)NCCNC([S-])=S
InChI Identifier
InChI=1S/C4H8N2S4.2Na/c7-3(8)5-1-2-6-4(9)10;;/h1-2H2,(H2,5,7,8)(H2,6,9,10);;/q;2*+1/p-2
InChI KeyUQJQVUOTMVCFHX-UHFFFAOYSA-L
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic alkali metal salts. These are organic salts of an alkali metal. The alkali metal atom is usually in its ionic form.
KingdomOrganic compounds  
Super ClassOrganic salts  
ClassOrganic metal salts  
Sub ClassOrganic alkali metal salts  
Direct ParentOrganic alkali metal salts  
Alternative Parents
Substituents
  • Organic alkali metal salt
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic sodium salt
    • 

  • Organosulfur compound
    • 

  • Organonitrogen compound
    • 

  • 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
logP0.59ALOGPS
logP1.97ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area24.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.76 m³·mol⁻¹ChemAxon
Polarizability20.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031224  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003248  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18748  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8891  
PDB IDNot Available
ChEBI ID81934  
Good Scents IDNot Available
References
General References
  1. Kuzan FB, Prahlad KV: The effects of 1, 2, 3, 4, 10, 10-hexachloro-1, 4, 4a, 5, 8, 8a-hexahydroxy endo, exo-5, 8-dimethionaphthalene (aldrin) and sodium ethylenebisdithiocarbomate (nabam) on the chick. Poult Sci. 1975 Jul;54(4):1054-64. doi: 10.3382/ps.0541054. [PubMed:1161698  ] 
  2. Miller PM, Stoddard EM: Increasing the Hatching of Eggs of Cyst and Rootknot Nematodes with Nabam. Science. 1958 Dec 5;128(3336):1429-30. doi: 10.1126/science.128.3336.1429. [PubMed:17797593  ] 
  3. Perez-Ruiz T, Martinez-Lozano C, Tomas V, Casajus R: Flow-injection fluorimetric determination of nabam and metham. Talanta. 1996 Feb;43(2):193-8. doi: 10.1016/0039-9140(95)01714-3. [PubMed:18966479  ] 
  4. Miles CJ, Zhou M: Determination of nabam fungicide in crops by liquid chromatography with postcolumn reaction detection. J Assoc Off Anal Chem. 1991 Mar-Apr;74(2):384-8. [PubMed:1904852  ] 
  5. Kurttio P, Savolainen K, Naukkarinen A, Kosma VM, Tuomisto L, Penttila I, Jolkkonen J: Urinary excretion of ethylenethiourea and kidney morphology in rats after continuous oral exposure to nabam or ethylenethiourea. Arch Toxicol. 1991;65(5):381-5. doi: 10.1007/BF02284260. [PubMed:1929852  ]