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Showing metabocard for 1-Butylamine (HMDB0031321)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:18 UTC
Update Date2023-02-21 17:20:22 UTC
HMDB IDHMDB0031321
Secondary Accession Numbers
  • HMDB31321
Metabolite Identification
Common Name1-Butylamine
Description1-Butylamine, also known as 1-aminobutan or N-C4H9NH2, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Butylamine is a colourless liquid which acquires a yellow colour upon storage in air. 1-Butylamine is an ammonia and fishy tasting compound. 1-Butylamine has been detected, but not quantified, in several different foods, such as cocoa and cocoa products, brassicas, fishes, garden tomato, and milk and milk products. This could make 1-butylamine a potential biomarker for the consumption of these foods. It is one of the four isomeric amines of butane. It is known to have the fishy, ammonia-like odor common to amines. Found in mulberry leaves, kale, swede, tomato, wheat bread, cheeses, caviar, raw fatty fish, cooked chicken or beef, beer, cocoa, and other foodstuffs.
Structure
Data?1677000022
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031321 (1-Butylamine)


  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    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
    0.0000    0.0000    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031321 (1-Butylamine)

HMDB0031321
     RDKit          3D
1-Butylamine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.1765    0.2069    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    0.5524    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -0.7228    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576   -0.5474    0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    0.3652   -0.5542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361    0.9729    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -0.7761    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    0.0845   -0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415    1.2574   -0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.9775    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.4530    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076   -1.1416   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288   -0.1818    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0431   -1.5373    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8894    0.9212   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5036    1.0221   -1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
M  END
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3D SDF for HMDB0031321 (1-Butylamine)


  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    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
    0.0000    0.0000    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031321

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3

> <INCHI_KEY>
HQABUPZFAYXKJW-UHFFFAOYSA-N

> <FORMULA>
C4H11N

> <MOLECULAR_WEIGHT>
73.1368

> <EXACT_MASS>
73.089149357

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
9.66287262827564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butan-1-amine

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
0.6984401493333334

> <ALOGPS_LOGS>
0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.205799730941068

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
23.7924

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031321 (1-Butylamine)

HMDB0031321
     RDKit          3D
1-Butylamine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.1765    0.2069    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    0.5524    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -0.7228    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576   -0.5474    0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    0.3652   -0.5542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361    0.9729    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -0.7761    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    0.0845   -0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415    1.2574   -0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.9775    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.4530    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076   -1.1416   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288   -0.1818    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0431   -1.5373    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8894    0.9212   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5036    1.0221   -1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
M  END
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PDB for HMDB0031321 (1-Butylamine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0031321 (1-Butylamine)

COMPND    HMDB0031321
HETATM    1  C1  UNL     1      -2.176   0.207   0.152  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.697   0.552   0.361  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.067  -0.723   0.194  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.558  -0.547   0.371  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.147   0.365  -0.554  1.00  0.00           N  
HETATM    6  H1  UNL     1      -2.836   0.973   0.590  1.00  0.00           H  
HETATM    7  H2  UNL     1      -2.375  -0.776   0.624  1.00  0.00           H  
HETATM    8  H3  UNL     1      -2.400   0.085  -0.928  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.441   1.257  -0.444  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.627   0.978   1.368  1.00  0.00           H  
HETATM   11  H6  UNL     1      -0.276  -1.453   0.939  1.00  0.00           H  
HETATM   12  H7  UNL     1      -0.108  -1.142  -0.803  1.00  0.00           H  
HETATM   13  H8  UNL     1       1.729  -0.182   1.402  1.00  0.00           H  
HETATM   14  H9  UNL     1       2.043  -1.537   0.249  1.00  0.00           H  
HETATM   15  H10 UNL     1       2.889   0.921  -0.080  1.00  0.00           H  
HETATM   16  H11 UNL     1       1.504   1.022  -1.011  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5   15   16
END
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SMILES for HMDB0031321 (1-Butylamine)

CCCCN
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INCHI for HMDB0031321 (1-Butylamine)

InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-AminobutanChEBI
1-AminobutaneChEBI
1-ButanamineChEBI
ButanamineChEBI
ButylamineChEBI
mono-N-ButylamineChEBI
MonobutylamineChEBI
N-ButylaminChEBI
N-ButylamineChEBI
N-C4H9NH2ChEBI
1-Butanamine, 9ciHMDB
AminobutaneHMDB
FEMA 3130HMDB
NorralamineHMDB
NorvalamineHMDB
N-Butylamine hydrobromideMeSH, HMDB
N-Butylamine hydrochloride, 14C-labeled CPDMeSH, HMDB
N-Butylamine hydrochlorideMeSH, HMDB
1-ButylamineChEBI
Chemical FormulaC4H11N
Average Molecular Weight73.1368
Monoisotopic Molecular Weight73.089149357
IUPAC Namebutan-1-amine
Traditional Namebutylamine
CAS Registry Number109-73-9
SMILES
CCCCN
InChI Identifier
InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3
InChI KeyHQABUPZFAYXKJW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-50 °CNot Available
Boiling Point77.00 to 78.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP0.97Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility80.7 g/LALOGPS
logP0.85ALOGPS
logP0.7ChemAxon
logS0.04ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.79 m³·mol⁻¹ChemAxon
Polarizability9.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+113.20831661259
DarkChem[M-H]-106.8331661259
DeepCCS[M+H]+121.81230932474
DeepCCS[M-H]-119.91730932474
DeepCCS[M-2H]-155.31630932474
DeepCCS[M+Na]+129.72430932474
AllCCS[M+H]+120.732859911
AllCCS[M+H-H2O]+116.132859911
AllCCS[M+NH4]+124.932859911
AllCCS[M+Na]+126.132859911
AllCCS[M-H]-134.232859911
AllCCS[M+Na-2H]-139.732859911
AllCCS[M+HCOO]-145.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.32 minutes32390414
Predicted by Siyang on May 30, 20229.0695 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20226.26 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid258.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid654.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid337.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid99.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid224.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid78.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid281.0 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 Acid286.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)614.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid645.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid135.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid714.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid256.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate681.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA430.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water171.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-ButylamineCCCCN911.6Standard polar33892256
1-ButylamineCCCCN588.2Standard non polar33892256
1-ButylamineCCCCN627.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Butylamine,1TMS,isomer #1CCCCN[Si](C)(C)C874.0Semi standard non polar33892256
1-Butylamine,1TMS,isomer #1CCCCN[Si](C)(C)C899.3Standard non polar33892256
1-Butylamine,2TMS,isomer #1CCCCN([Si](C)(C)C)[Si](C)(C)C1146.0Semi standard non polar33892256
1-Butylamine,2TMS,isomer #1CCCCN([Si](C)(C)C)[Si](C)(C)C1117.3Standard non polar33892256
1-Butylamine,1TBDMS,isomer #1CCCCN[Si](C)(C)C(C)(C)C1102.1Semi standard non polar33892256
1-Butylamine,1TBDMS,isomer #1CCCCN[Si](C)(C)C(C)(C)C1087.6Standard non polar33892256
1-Butylamine,2TBDMS,isomer #1CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1521.0Semi standard non polar33892256
1-Butylamine,2TBDMS,isomer #1CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1500.3Standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03659
Phenol Explorer Compound IDNot Available
FooDB IDFDB003380
KNApSAcK IDC00050486
Chemspider ID7716
KEGG Compound IDNot Available
BioCyc IDBUTYLAMINE
BiGG IDNot Available
Wikipedia LinkN-Butylamine
METLIN IDNot Available
PubChem Compound8007
PDB IDLYT
ChEBI ID43799
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .