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Showing metabocard for Butanal (HMDB0003543)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 23:25:38 UTC
Update Date2023-02-21 17:16:43 UTC
HMDB IDHMDB0003543
Secondary Accession Numbers
  • HMDB03543
Metabolite Identification
Common NameButanal
DescriptionButanal, also known as butyral or butyl aldehyde, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. It is miscible with most organic solvents. Butanal exists in all living organisms, ranging from bacteria to humans. Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid. Butanal is an apple, bready, and chocolate tasting compound. Outside of the human body, Butanal is found, on average, in the highest concentration within cow milk and carrots. Butanal has also been detected, but not quantified in several different foods, such as hard wheats, borages, ostrich ferns, skunk currants, and fennels. This could make butanal a potential biomarker for the consumption of these foods. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand Tppts. Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:CH3CHCH2 + H2 + CO → CH3CH2CH2CHO. Traditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. This compound is the aldehyde derivative of butane. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. It is a colourless flammable liquid with an unpleasant smell.
Structure
Data?1676999803
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003543 (Butanal)


  Mrv1652309042000302D          

  5  4  0  0  0  0            999 V2000
   -1.0717    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0003543 (Butanal)

HMDB0003543
     RDKit          3D
Butanal
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.2744    0.8200    0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.4385   -0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -0.7594    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236    0.1942   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692    0.8230   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4609    1.3812    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    0.5547    1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929    1.3573   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570   -1.2903   -0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826   -0.4423   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414   -0.8065    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.7473   -0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    0.3539    0.5396 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  2  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
M  END
Download

3D SDF for HMDB0003543 (Butanal)


  Mrv1652309042000302D          

  5  4  0  0  0  0            999 V2000
   -1.0717    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003543

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3

> <INCHI_KEY>
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N

> <FORMULA>
C4H8O

> <MOLECULAR_WEIGHT>
72.1057

> <EXACT_MASS>
72.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.317781240506022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butanal

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.763142545333333

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.972134580297713

> <JCHEM_PKA_STRONGEST_BASIC>
-6.944082299855082

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
20.946199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butoxide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0003543 (Butanal)

HMDB0003543
     RDKit          3D
Butanal
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.2744    0.8200    0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.4385   -0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -0.7594    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236    0.1942   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692    0.8230   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4609    1.3812    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    0.5547    1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929    1.3573   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570   -1.2903   -0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826   -0.4423   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414   -0.8065    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.7473   -0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    0.3539    0.5396 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  2  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
M  END
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PDB for HMDB0003543 (Butanal)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      -2.001   1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2                                                            
CONECT    5    1    3                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0003543 (Butanal)

COMPND    HMDB0003543
HETATM    1  C1  UNL     1      -1.274   0.820   0.217  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.682  -0.439  -0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.662  -0.759   0.218  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.724   0.194  -0.136  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.769   0.823  -1.189  1.00  0.00           O  
HETATM    6  H1  UNL     1      -0.461   1.381   0.696  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.988   0.555   1.036  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.793   1.357  -0.591  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.357  -1.290  -0.087  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.683  -0.442  -1.477  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.541  -0.806   1.326  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.974  -1.747  -0.193  1.00  0.00           H  
HETATM   13  H8  UNL     1       2.568   0.354   0.540  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5    5   13
END
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SMILES for HMDB0003543 (Butanal)

CCCC=O
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INCHI for HMDB0003543 (Butanal)

InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-ButanalChEBI
Aldehyde butyriqueChEBI
Aldeide butirricaChEBI
ButalChEBI
ButaldehydeChEBI
Butan-1-alChEBI
ButanaldehydeChEBI
Butyl aldehydeChEBI
ButylaldehydeChEBI
ButyralChEBI
ButyraldehydChEBI
ButyraldehydeChEBI
Butyric aldehydeChEBI
ButyrylaldehydeChEBI
N-ButanalChEBI
N-Butyl aldehydeChEBI
N-ButyraldehydeChEBI
N-C3H7CHOChEBI
ButalydeHMDB
N-ButylaldehydeHMDB
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Namebutanal
Traditional Namebutoxide
CAS Registry Number123-72-8
SMILES
CCCC=O
InChI Identifier
InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
InChI KeyZTQSAGDEMFDKMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-99 °CNot Available
Boiling Point74.00 to 75.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility71 mg/mL at 25 °CNot Available
LogP0.88HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility50.9 g/LALOGPS
logP1.1ALOGPS
logP0.76ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)17.97ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.95 m³·mol⁻¹ChemAxon
Polarizability8.32 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]+113.07331661259
DarkChem[M-H]-106.63931661259
DeepCCS[M+H]+121.90330932474
DeepCCS[M-H]-120.00830932474
DeepCCS[M-2H]-155.35230932474
DeepCCS[M+Na]+129.46530932474
AllCCS[M+H]+121.032859911
AllCCS[M+H-H2O]+116.432859911
AllCCS[M+NH4]+125.232859911
AllCCS[M+Na]+126.432859911
AllCCS[M-H]-134.132859911
AllCCS[M+Na-2H]-139.632859911
AllCCS[M+HCOO]-145.732859911

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, 2022.2.64 minutes32390414
Predicted by Siyang on May 30, 202212.5402 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.25 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1418.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid485.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid193.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid341.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid209.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid461.2 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 Acid559.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)253.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid961.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid346.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1113.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid355.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid326.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate608.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA473.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water117.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButanalCCCC=O861.1Standard polar33892256
ButanalCCCC=O560.1Standard non polar33892256
ButanalCCCC=O588.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butanal,1TMS,isomer #1CCC=CO[Si](C)(C)C830.3Semi standard non polar33892256
Butanal,1TMS,isomer #1CCC=CO[Si](C)(C)C786.7Standard non polar33892256
Butanal,1TMS,isomer #1CCC=CO[Si](C)(C)C915.1Standard polar33892256
Butanal,1TBDMS,isomer #1CCC=CO[Si](C)(C)C(C)(C)C1053.2Semi standard non polar33892256
Butanal,1TBDMS,isomer #1CCC=CO[Si](C)(C)C(C)(C)C1028.3Standard non polar33892256
Butanal,1TBDMS,isomer #1CCC=CO[Si](C)(C)C(C)(C)C1120.5Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Feces
Tissue Locations
  • Blood
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003378
KNApSAcK IDC00050431
Chemspider ID256
KEGG Compound IDC01412
BioCyc IDBUTANAL
BiGG IDNot Available
Wikipedia LinkButanal
METLIN ID6947
PubChem Compound261
PDB IDNot Available
ChEBI ID15743
Food Biomarker OntologyNot Available
VMH IDBTAL
MarkerDB IDNot Available
Good Scents IDrw1007681
References
Synthesis ReferenceWeizmann, Charles; Garrard, Stanley Frederick. Some condensations of butyl alcohol and butyraldehyde. Journal of the Chemical Society, Transactions (1920), 117 324-38.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Orhan H, van Holland B, Krab B, Moeken J, Vermeulen NP, Hollander P, Meerman JH: Evaluation of a multi-parameter biomarker set for oxidative damage in man: increased urinary excretion of lipid, protein and DNA oxidation products after one hour of exercise. Free Radic Res. 2004 Dec;38(12):1269-79. [PubMed:15763951 ]
  2. Holley AE, Walker MK, Cheeseman KH, Slater TF: Measurement of n-alkanals and hydroxyalkenals in biological samples. Free Radic Biol Med. 1993 Sep;15(3):281-9. [PubMed:8406128 ]

Enzymes

Enzyme Details
1. Retinol dehydrogenase 13
General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8