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Showing metabocard for Isopentanol (HMDB0006007)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 20:14:15 UTC
Update Date2023-02-21 17:17:11 UTC
HMDB IDHMDB0006007
Secondary Accession Numbers
  • HMDB06007
Metabolite Identification
Common NameIsopentanol
DescriptionIsopentanol, also known as isoamyl alcohol or 3-methylbutanol, 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). Thus, isopentanol is considered to be a fatty alcohol lipid molecule. Isopentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Isopentanol exists in all eukaryotes, ranging from yeast to humans. Isopentanol is an alcoholic, banana, and burnt tasting compound. Isopentanol is found, on average, in the highest concentration within milk (cow). Isopentanol has also been detected, but not quantified, in several different foods, such as chinese cinnamons, grapefruits, walnuts, wild leeks, and spearmints. This could make isopentanol a potential biomarker for the consumption of these foods. Isopentanol is one of several isomers of amyl alcohol. Isopentanol is the major higher chain alcohol in alcoholic beverages and is present in cider, mead, beer, wine, and spirits to varying degrees, being obtained by the fermentation of starches. Isopentanol, with regard to humans, has been found to be associated with the diseases such as ulcerative colitis; isopentanol has also been linked to the inborn metabolic disorder celiac disease. Isopentanol is a metabolite found in Escherichia (PMID:18676713 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006007 (Isopentanol)

  Mrv1652309272007432D          

  6  5  0  0  1  0            999 V2000
   -0.9596    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0006007 (Isopentanol)

HMDB0006007
     RDKit          3D
Isopentanol
 18 17  0  0  0  0  0  0  0  0999 V2000
   -0.9778   -1.2669    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418    0.2037    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    1.0443   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911    0.4900   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154   -0.3813    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -0.2095   -0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -1.7291   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -1.4125   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541   -1.8271    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5656    0.4061    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5536    1.2731   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    0.4512   -0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    1.9991    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    0.2485   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266    1.5704   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -0.1070    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.4328    0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296    0.6798   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
M  END
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3D SDF for HMDB0006007 (Isopentanol)

  Mrv1652309272007432D          

  6  5  0  0  1  0            999 V2000
   -0.9596    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006007

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3

> <INCHI_KEY>
PHTQWCKDNZKARW-UHFFFAOYSA-N

> <FORMULA>
C5H12O

> <MOLECULAR_WEIGHT>
88.1482

> <EXACT_MASS>
88.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.028464538980348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutan-1-ol

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.0923410423333335

> <ALOGPS_LOGS>
-0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.166789338364286

> <JCHEM_PKA_STRONGEST_BASIC>
-1.851046343399461

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
26.6835

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoamyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0006007 (Isopentanol)

HMDB0006007
     RDKit          3D
Isopentanol
 18 17  0  0  0  0  0  0  0  0999 V2000
   -0.9778   -1.2669    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418    0.2037    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    1.0443   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911    0.4900   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154   -0.3813    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966   -0.2095   -0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -1.7291   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -1.4125   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541   -1.8271    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5656    0.4061    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5536    1.2731   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    0.4512   -0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    1.9991    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    0.2485   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266    1.5704   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -0.1070    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.4328    0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296    0.6798   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
M  END
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PDB for HMDB0006007 (Isopentanol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.791   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.125   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.791   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.458   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.876   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.210   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0006007 (Isopentanol)

COMPND    HMDB0006007
HETATM    1  C1  UNL     1      -0.978  -1.267   0.154  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.642   0.204   0.316  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.750   1.044  -0.308  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.691   0.490  -0.347  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.715  -0.381   0.353  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.997  -0.209  -0.169  1.00  0.00           O  
HETATM    7  H1  UNL     1      -0.397  -1.729  -0.672  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.050  -1.412  -0.113  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.754  -1.827   1.097  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.566   0.406   1.422  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.554   1.273  -1.357  1.00  0.00           H  
HETATM   12  H6  UNL     1      -2.686   0.451  -0.169  1.00  0.00           H  
HETATM   13  H7  UNL     1      -1.810   1.999   0.245  1.00  0.00           H  
HETATM   14  H8  UNL     1       0.586   0.248  -1.407  1.00  0.00           H  
HETATM   15  H9  UNL     1       0.927   1.570  -0.192  1.00  0.00           H  
HETATM   16  H10 UNL     1       1.763  -0.107   1.426  1.00  0.00           H  
HETATM   17  H11 UNL     1       1.378  -1.433   0.290  1.00  0.00           H  
HETATM   18  H12 UNL     1       3.130   0.680  -0.570  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6   18
END
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SMILES for HMDB0006007 (Isopentanol)

CC(C)CCO
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INCHI for HMDB0006007 (Isopentanol)

InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H12O
Average Molecular Weight88.1482
Monoisotopic Molecular Weight88.088815006
IUPAC Name3-methylbutan-1-ol
Traditional Nameisoamyl alcohol
CAS Registry Number123-51-3
SMILES
CC(C)CCO
InChI Identifier
InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
InChI KeyPHTQWCKDNZKARW-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 locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-117.2 °CNot Available
Boiling Point131.00 to 133.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility26.7 mg/mL at 25 °CNot Available
LogP1.16HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0-270567.0677 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal 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 and Quantified0-185974.681 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac 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 ]
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 ]
Associated OMIM IDs
DrugBank IDDB02296
Phenol Explorer Compound IDNot Available
FooDB IDFDB008131
KNApSAcK IDC00050468
Chemspider ID29000
KEGG Compound IDC07328
BioCyc IDCPD-7032
BiGG IDNot Available
Wikipedia LinkIsoamyl alcohol
METLIN IDNot Available
PubChem Compound31260
PDB IDIP3
ChEBI ID15837
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boumba VA, Ziavrou KS, Vougiouklakis T: Biochemical pathways generating post-mortem volatile compounds co-detected during forensic ethanol analyses. Forensic Sci Int. 2008 Jan 30;174(2-3):133-51. Epub 2007 Apr 23. [PubMed:17452087 ]
  2. Kostrubsky VE, Strom SC, Wood SG, Wrighton SA, Sinclair PR, Sinclair JF: Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Arch Biochem Biophys. 1995 Oct 1;322(2):516-20. [PubMed:7574728 ]
  3. Connor MR, Liao JC: Engineering of an Escherichia coli strain for the production of 3-methyl-1-butanol. Appl Environ Microbiol. 2008 Sep;74(18):5769-75. doi: 10.1128/AEM.00468-08. Epub 2008 Aug 1. [PubMed:18676713 ]

Enzymes

Enzyme Details
1. Renin
General function:
Involved in aspartic-type endopeptidase activity
Specific function:
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of blood pressure and increased sodium retention by the kidney
Gene Name:
REN
Uniprot ID:
P00797
Molecular weight:
45057.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]