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Showing metabocard for 2-Butanol (HMDB0011469)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-12-23 16:50:59 UTC
Update Date2023-02-21 17:17:28 UTC
HMDB IDHMDB0011469
Secondary Accession Numbers
  • HMDB11469
Metabolite Identification
Common Name2-Butanol
Description2-Butanol, also known as 2-butyl alcohol or 2-hydroxybutane, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). 2-Butanol is an odorless tasting compound. Based on a literature review very few articles have been published on 2-Butanol.
Structure
Data?1676999848
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0011469 (2-Butanol)


  Mrv1652305261923532D          

  5  4  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0  0  0  0
  2  1  1  0  0  0  0
  2  4  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
Download

3D MOL for HMDB0011469 (2-Butanol)

HMDB0011469
     RDKit          3D
2-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.9701    0.2475   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609   -0.2414    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.0300   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344   -0.5664    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    1.3229   -0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463    1.1775    0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299    0.5414   -1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -0.5075    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -1.3156    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    0.2720    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.5625   -1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4704    0.2715    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.9052    1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -1.4387   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4019    1.7346   -0.3540 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
  3  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
  4 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
Download

3D SDF for HMDB0011469 (2-Butanol)


  Mrv1652305261923532D          

  5  4  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0  0  0  0
  2  1  1  0  0  0  0
  2  4  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011469

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3

> <INCHI_KEY>
BTANRVKWQNVYAZ-UHFFFAOYSA-N

> <FORMULA>
C4H10O

> <MOLECULAR_WEIGHT>
74.1216

> <EXACT_MASS>
74.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.073301050575438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butan-2-ol

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.7773283056666666

> <ALOGPS_LOGS>
0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.68625361490547

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6238326688403468

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
21.9527

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-butanol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0011469 (2-Butanol)

HMDB0011469
     RDKit          3D
2-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.9701    0.2475   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609   -0.2414    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.0300   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344   -0.5664    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    1.3229   -0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463    1.1775    0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299    0.5414   -1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -0.5075    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -1.3156    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    0.2720    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.5625   -1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4704    0.2715    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.9052    1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -1.4387   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4019    1.7346   -0.3540 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
  3  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
  4 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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PDB for HMDB0011469 (2-Butanol)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    5    1    4                                                  
CONECT    3    4                                                            
CONECT    4    2    3                                                       
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0011469 (2-Butanol)

COMPND    HMDB0011469
HETATM    1  C1  UNL     1       1.970   0.247  -0.083  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.661  -0.241   0.457  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.485  -0.030  -0.507  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.734  -0.566   0.165  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.610   1.323  -0.787  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.246   1.178   0.474  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.930   0.541  -1.149  1.00  0.00           H  
HETATM    8  H3  UNL     1       2.796  -0.507   0.041  1.00  0.00           H  
HETATM    9  H4  UNL     1       0.774  -1.316   0.708  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.371   0.272   1.410  1.00  0.00           H  
HETATM   11  H6  UNL     1      -0.357  -0.563  -1.455  1.00  0.00           H  
HETATM   12  H7  UNL     1      -2.470   0.272   0.251  1.00  0.00           H  
HETATM   13  H8  UNL     1      -1.543  -0.905   1.204  1.00  0.00           H  
HETATM   14  H9  UNL     1      -2.146  -1.439  -0.374  1.00  0.00           H  
HETATM   15  H10 UNL     1      -1.402   1.735  -0.354  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4    5   11
CONECT    4   12   13   14
CONECT    5   15
END
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SMILES for HMDB0011469 (2-Butanol)

CCC(C)O
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INCHI for HMDB0011469 (2-Butanol)

InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Methyl-1-propanolChEBI
1-Methylpropyl alcoholChEBI
2-Butyl alcoholChEBI
2-HydroxybutaneChEBI
Butanol-2ChEBI
MethylethylcarbinolChEBI
S-Butyl alcoholChEBI
S-ButylalkoholChEBI
Sec-butanolChEBI
Sec-butyl alcoholChEBI
2-ButanolChEBI
2-Butanol, (+)-isomerMeSH, HMDB
2-Butanol, (-)-isomerMeSH, HMDB
2-Butanol, lithium salt, (S)-isomerMeSH, HMDB
2-Butanol, aluminum saltMeSH, HMDB
2-Butanol, lithium salt, (R)-isomerMeSH, HMDB
2-Butanol, (+-)-isomerMeSH, HMDB
2-Butanol, lithium salt, (+-)-isomerMeSH, HMDB
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Namebutan-2-ol
Traditional Name2-butanol
CAS Registry Number78-92-2
SMILES
CCC(C)O
InChI Identifier
InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
InChI KeyBTANRVKWQNVYAZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-114.7 °CNot Available
Boiling Point99.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility181 mg/mL at 25 °CNot Available
LogP0.61HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility195 g/LALOGPS
logP0.66ALOGPS
logP0.78ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.95 m³·mol⁻¹ChemAxon
Polarizability9.07 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]+113.55731661259
DarkChem[M-H]-106.5831661259
DeepCCS[M+H]+125.53430932474
DeepCCS[M-H]-123.63930932474
DeepCCS[M-2H]-159.28830932474
DeepCCS[M+Na]+133.73830932474
AllCCS[M+H]+122.032859911
AllCCS[M+H-H2O]+117.532859911
AllCCS[M+NH4]+126.232859911
AllCCS[M+Na]+127.432859911
AllCCS[M-H]-134.532859911
AllCCS[M+Na-2H]-140.132859911
AllCCS[M+HCOO]-146.232859911

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, 2022.1.39 minutes32390414
Predicted by Siyang on May 30, 202210.6974 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.3 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid71.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1358.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid401.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid123.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid247.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid87.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid373.7 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 Acid443.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)126.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid754.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid304.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1005.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid277.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid280.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate447.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA366.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water75.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-ButanolCCC(C)O981.7Standard polar33892256
2-ButanolCCC(C)O570.1Standard non polar33892256
2-ButanolCCC(C)O594.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Butanol,1TMS,isomer #1CCC(C)O[Si](C)(C)C770.4Semi standard non polar33892256
2-Butanol,1TBDMS,isomer #1CCC(C)O[Si](C)(C)C(C)(C)C969.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
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 QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified313.0 (54.0-863.0) uMAdult (>18 years old)BothAlcohol intoxication details
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
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed:2779169 ]
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 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. 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 ]
Ulcerative colitis
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016802
KNApSAcK IDC00053987
Chemspider ID6320
KEGG Compound IDNot Available
BioCyc IDCPD-326
BiGG IDNot Available
Wikipedia Link2-butanol
METLIN IDNot Available
PubChem Compound6568
PDB IDNot Available
ChEBI ID35687
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available