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Showing metabocard for Carbamic acid (HMDB0003551)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:34:27 UTC
Update Date2023-02-21 17:16:44 UTC
HMDB IDHMDB0003551
Secondary Accession Numbers
  • HMDB03551
Metabolite Identification
Common NameCarbamic acid
DescriptionCarbamic acid is occasionally found as carbamate in workers exposed to pesticides. Carbamates, particularly carbofuran, seem to be more associated with exuberant and diversified symptomatology of pesticide exposure than organophosphates. Neurological symptoms occur among farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides such as carbamates. Carbamic acid products of several amines, such as beta-N-methylamino-L-alanine (BMAA), ethylenediamine, and L-cysteine have been implicated in toxicity. Studies suggested that a significant portion of amino-compounds in biological samples (that naturally contain CO2/bicarbonate) can be present as a carbamic acid. The formation of carbamate glucuronide metabolites has been described for numerous pharmaceuticals and they have been identified in all of the species commonly used in drug metabolism studies (rat, dog, mouse, rabbit, guinea pig, and human). There has been no obvious species specificity for their formation and no preference for 1 or 2 degree amines. Many biological reactions have also been described in the literature that involve the reaction of CO2 with amino groups of biomolecules. For example, CO2 generated from cellular respiration is expired in part through the reversible formation of a carbamate between CO2 and the -amino groups of the alpha and beta-chains of hemoglobin. Glucuronidation is an important mechanism used by mammalian systems to clear and eliminate both endogenous and foreign chemicals. Many functional groups are susceptible to conjugation with glucuronic acid, including hydroxyls, phenols, carboxyls, activated carbons, thiols, amines, and selenium. Primary and secondary amines can also react with carbon dioxide (CO2) via a reversible reaction to form a carbamic acid. The carbamic acid is also a substrate for glucuronidation and results in a stable carbamate glucuronide metabolite. The detection and characterization of these products has been facilitated greatly by the advent of soft ionization mass spectrometry techniques and high field NMR instrumentation. (PMID: 16268118 , 17168688 , 12929145 ).
Structure
Data?1676999804
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003551 (Carbamic acid)


  Mrv1652309102018452D          

  4  3  0  0  0  0            999 V2000
    0.7145   -0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
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3D MOL for HMDB0003551 (Carbamic acid)

HMDB0003551
     RDKit          3D
Carbamic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    0.9349   -0.3274    0.0300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.5206   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    1.7195   -0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    0.1032    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228   -0.0282   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.2349    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -0.7528    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  4  7  1  0
M  END
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3D SDF for HMDB0003551 (Carbamic acid)


  Mrv1652309102018452D          

  4  3  0  0  0  0            999 V2000
    0.7145   -0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003551

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)

> <INCHI_KEY>
KXDHJXZQYSOELW-UHFFFAOYSA-N

> <FORMULA>
CH3NO2

> <MOLECULAR_WEIGHT>
61.04

> <EXACT_MASS>
61.016378345

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
4.678537514102712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
carbamic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-0.5568912479999999

> <ALOGPS_LOGS>
0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9193795751141347

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
11.3204

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0003551 (Carbamic acid)

HMDB0003551
     RDKit          3D
Carbamic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    0.9349   -0.3274    0.0300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.5206   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    1.7195   -0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4737    0.1032    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228   -0.0282   -0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.2349    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -0.7528    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  4  7  1  0
M  END
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PDB for HMDB0003551 (Carbamic acid)

HEADER    PROTEIN                                 10-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-20         0                                  
HETATM    1  N   UNK     0       1.334  -1.155   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -1.155   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0003551 (Carbamic acid)

COMPND    HMDB0003551
HETATM    1  N1  UNL     1       0.935  -0.327   0.030  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.209   0.521  -0.038  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.075   1.720  -0.417  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.474   0.103   0.289  1.00  0.00           O  
HETATM    5  H1  UNL     1       1.823  -0.028  -0.425  1.00  0.00           H  
HETATM    6  H2  UNL     1       0.911  -1.235   0.520  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.910  -0.753   0.041  1.00  0.00           H  
CONECT    1    2    5    6
CONECT    2    3    3    4
CONECT    4    7
END
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SMILES for HMDB0003551 (Carbamic acid)

NC(O)=O
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INCHI for HMDB0003551 (Carbamic acid)

InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
AminoameisensaeureChEBI
Aminoformic acidChEBI
CarbamateChEBI
CarbamidsaeureChEBI
AminoformateGenerator
Carbamate ionHMDB
Chlorphenesin carbamateHMDB
MaolateHMDB
Calcium carbamateMeSH, HMDB
Carbamic acid, potassium saltMeSH, HMDB
Carbamic acid, sodium saltMeSH, HMDB
Sodium carbamateMeSH, HMDB
Ammonium carbamateMeSH, HMDB
Carbamic acid, ammonia saltMeSH, HMDB
Carbamic acid, calcium saltMeSH, HMDB
Potassium carbamateMeSH, HMDB
Chemical FormulaCH3NO2
Average Molecular Weight61.04
Monoisotopic Molecular Weight61.016378345
IUPAC Namecarbamic acid
Traditional Namecarbamic acid
CAS Registry Number463-77-4
SMILES
NC(O)=O
InChI Identifier
InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)
InChI KeyKXDHJXZQYSOELW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic carbonic acids and derivatives. Organic carbonic acids and derivatives are compounds comprising the organic carbonic acid or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassNot Available
Direct ParentOrganic carbonic acids and derivatives
Alternative Parents
Substituents
  • Carbonic acid derivative
  • Carbamic acid derivative
  • Carbamic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility379 g/LALOGPS
logP-1.1ALOGPS
logP-0.56ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.32 m³·mol⁻¹ChemAxon
Polarizability4.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+107.85631661259
DarkChem[M-H]-99.57231661259
DeepCCS[M+H]+122.26430932474
DeepCCS[M-H]-120.36930932474
DeepCCS[M-2H]-156.2330932474
DeepCCS[M+Na]+130.58130932474
AllCCS[M+H]+108.932859911
AllCCS[M+H-H2O]+104.432859911
AllCCS[M+NH4]+113.132859911
AllCCS[M+Na]+114.332859911
AllCCS[M-H]-138.132859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-152.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 20228.6463 minutes33406817
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid336.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid567.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid383.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid106.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid293.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid157.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid266.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid283.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)746.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid583.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid53.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid665.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid238.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid366.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate683.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA381.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water371.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carbamic acidNC(O)=O2100.1Standard polar33892256
Carbamic acidNC(O)=O767.8Standard non polar33892256
Carbamic acidNC(O)=O1104.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carbamic acid,1TMS,isomer #1C[Si](C)(C)OC(N)=O960.8Semi standard non polar33892256
Carbamic acid,1TMS,isomer #2C[Si](C)(C)NC(=O)O1074.6Semi standard non polar33892256
Carbamic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)O[Si](C)(C)C1067.5Semi standard non polar33892256
Carbamic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)O[Si](C)(C)C1073.8Standard non polar33892256
Carbamic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)O[Si](C)(C)C1245.9Standard polar33892256
Carbamic acid,2TMS,isomer #2C[Si](C)(C)N(C(=O)O)[Si](C)(C)C1201.3Semi standard non polar33892256
Carbamic acid,2TMS,isomer #2C[Si](C)(C)N(C(=O)O)[Si](C)(C)C1052.1Standard non polar33892256
Carbamic acid,2TMS,isomer #2C[Si](C)(C)N(C(=O)O)[Si](C)(C)C1242.1Standard polar33892256
Carbamic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1176.8Semi standard non polar33892256
Carbamic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1148.2Standard non polar33892256
Carbamic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1125.1Standard polar33892256
Carbamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(N)=O1165.2Semi standard non polar33892256
Carbamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)O1264.0Semi standard non polar33892256
Carbamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C1502.7Semi standard non polar33892256
Carbamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C1436.3Standard non polar33892256
Carbamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C1471.4Standard polar33892256
Carbamic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C1569.5Semi standard non polar33892256
Carbamic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C1447.5Standard non polar33892256
Carbamic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C1482.9Standard polar33892256
Carbamic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1834.6Semi standard non polar33892256
Carbamic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1788.6Standard non polar33892256
Carbamic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1557.8Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Neuron
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04261
Phenol Explorer Compound IDNot Available
FooDB IDFDB023195
KNApSAcK IDC00016003
Chemspider ID271
KEGG Compound IDC01563
BioCyc IDCARBAMATE
BiGG IDNot Available
Wikipedia LinkCarbamic_acid
METLIN ID6950
PubChem Compound277
PDB IDNot Available
ChEBI ID28616
Food Biomarker OntologyNot Available
VMH IDCBMT
MarkerDB IDNot Available
Good Scents IDrw1904011
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rendon von Osten J, Epomex C, Tinoco-Ojanguren R, Soares AM, Guilhermino L: Effect of pesticide exposure on acetylcholinesterase activity in subsistence farmers from Campeche, Mexico. Arch Environ Health. 2004 Aug;59(8):418-25. [PubMed:16268118 ]
  2. Schaefer WH: Reaction of primary and secondary amines to form carbamic acid glucuronides. Curr Drug Metab. 2006 Dec;7(8):873-81. [PubMed:17168688 ]
  3. Smit LA, van-Wendel-de-Joode BN, Heederik D, Peiris-John RJ, van der Hoek W: Neurological symptoms among Sri Lankan farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides. Am J Ind Med. 2003 Sep;44(3):254-64. [PubMed:12929145 ]