Hmdb loader

Showing metabocard for 1-Butanol (HMDB0004327)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (34) Show 34 proteinsXML
enzymes (34) Show 34 proteins
Show more...Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 16:50:24 UTC
Update Date2023-02-21 17:17:00 UTC
HMDB IDHMDB0004327
Secondary Accession Numbers
  • HMDB04327
Metabolite Identification
Common Name1-Butanol
Description1-Butanol, which is also known as n-butanol or 1-butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermenetation through the butanoate metabolic pathway. It has been found in Bacillus, Clostridium, Escherichia, Lactobacillus, Pseudomonas, Saccharomyces, Synechococcus and Thermoanaerobacterium.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004327 (1-Butanol)

  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 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0004327 (1-Butanol)

HMDB0004327
     RDKit          3D
1-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.5192   -0.3178    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -0.1222   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.4929   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    0.2620    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    1.6179   -0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6395   -0.3839    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.2713    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    0.5433    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.7271   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.9361   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -1.5787   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -0.2721   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.0802    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635   -0.1405    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.8670   -0.6860 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
M  END
Download

3D SDF for HMDB0004327 (1-Butanol)

  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 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004327

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

> <INCHI_KEY>
LRHPLDYGYMQRHN-UHFFFAOYSA-N

> <FORMULA>
C4H10O

> <MOLECULAR_WEIGHT>
74.1216

> <EXACT_MASS>
74.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.214856371458051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butan-1-ol

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.805321946

> <ALOGPS_LOGS>
0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.954258074443697

> <JCHEM_PKA_STRONGEST_BASIC>
-1.944007518238327

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
22.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butanol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0004327 (1-Butanol)

HMDB0004327
     RDKit          3D
1-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.5192   -0.3178    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -0.1222   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.4929   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    0.2620    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    1.6179   -0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6395   -0.3839    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.2713    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    0.5433    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.7271   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.9361   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -1.5787   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -0.2721   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.0802    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635   -0.1405    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.8670   -0.6860 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
M  END
Download

PDB for HMDB0004327 (1-Butanol)

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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+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
Download

3D PDB for HMDB0004327 (1-Butanol)

COMPND    HMDB0004327
HETATM    1  C1  UNL     1      -1.519  -0.318   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.959  -0.122  -0.488  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.466  -0.493  -0.677  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.434   0.262   0.189  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.416   1.618  -0.003  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.639  -0.384   0.757  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.226  -1.271   1.353  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.370   0.543   1.558  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.563  -0.727  -1.197  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.123   0.936  -0.779  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.642  -1.579  -0.536  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.732  -0.272  -1.733  1.00  0.00           H  
HETATM   13  H8  UNL     1       1.145   0.080   1.266  1.00  0.00           H  
HETATM   14  H9  UNL     1       2.463  -0.140   0.100  1.00  0.00           H  
HETATM   15  H10 UNL     1       2.101   1.867  -0.686  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
END
Download

SMILES for HMDB0004327 (1-Butanol)

CCCCO
Download

INCHI for HMDB0004327 (1-Butanol)

InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
Download
View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Namebutan-1-ol
Traditional Namebutanol
CAS Registry Number71-36-3
SMILES
CCCCO
InChI Identifier
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
InChI KeyLRHPLDYGYMQRHN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-89.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility63.2 mg/mL at 25 °CNot Available
LogP0.88HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Pancreas
  • Spleen
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Liebich HM, Buelow HJ, Kallmayer R: Quantification of endogenous aliphatic alcohols in serum and urine. J Chromatogr. 1982 Apr 30;239:343-9. [PubMed:7096503 ]
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. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  3. 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 ]
  4. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  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 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Irritable bowel syndrome
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Associated OMIM IDs
DrugBank IDDB02145
Phenol Explorer Compound IDNot Available
FooDB IDFDB031032
KNApSAcK IDC00035814
Chemspider ID258
KEGG Compound IDC06142
BioCyc IDBUTANOL
BiGG IDNot Available
Wikipedia LinkN-Butanol
METLIN ID7052
PubChem Compound263
PDB ID1BO
ChEBI ID28885
Food Biomarker OntologyNot Available
VMH IDBTOH
MarkerDB IDMDB00000446
Good Scents IDNot Available
References
Synthesis ReferenceTsuchida, Takashi; Sakuma, Shuji. Ethanol to 1-butanol on hydroxyapatite. Shokubai (2007), 49(3), 238-243.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 34 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Serum paraoxonase/lactonase 3
General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Enzyme Details
2. Serum paraoxonase/arylesterase 1
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Enzyme Details
3. Serum paraoxonase/arylesterase 2
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Enzyme Details
4. Intestinal-type alkaline phosphatase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
Enzyme Details
5. Lysosomal acid phosphatase
General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
Enzyme Details
6. Alkaline phosphatase, tissue-nonspecific isozyme
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
Enzyme Details
7. Tartrate-resistant acid phosphatase type 5
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
Enzyme Details
8. Alkaline phosphatase, placental-like
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
Enzyme Details
9. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Enzyme Details
10. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595

Only showing the first 10 proteins. There are 34 proteins in total.

Show all enzymes and transporters