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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:25:49 UTC

Update Date

2023-02-21 17:23:30 UTC

HMDB ID

HMDB0033676

Secondary Accession Numbers

HMDB33676

Metabolite Identification

Common Name

(±)-3-Methyl-1-pentanol

Description

(±)-3-Methyl-1-pentanol, also known as 3-ethylbutanol or 3-methyl-(+/-)-1-pentanol, 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). (±)-3-Methyl-1-pentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (±)-3-Methyl-1-pentanol is considered to be a fatty alcohol lipid molecule. (±)-3-Methyl-1-pentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. (±)-3-Methyl-1-pentanol is a cocoa, cognac, and fruity tasting compound. (±)-3-Methyl-1-pentanol has been detected, but not quantified, in cornmints.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Ethylbutanol	ChEBI
2-Ethyl-4-butanol	HMDB
3-Ethyl-1-butanol	HMDB
3-Methyl-(.+/-.)-1-pentanol	HMDB
3-Methyl-1-pentanol	HMDB
3-Methylpentan-1-ol	HMDB
3-Methylpentanol	HMDB

Chemical Formula

C₆H₁₄O

Average Molecular Weight

102.1748

Monoisotopic Molecular Weight

102.10446507

IUPAC Name

3-methylpentan-1-ol

Traditional Name

3-methyl-1-pentanol

CAS Registry Number

20281-83-8

SMILES

CCC(C)CCO

InChI Identifier

InChI=1S/C6H14O/c1-3-6(2)4-5-7/h6-7H,3-5H2,1-2H3

InChI Key

IWTBVKIGCDZRPL-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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:87381 )
Fatty alcohols (LMFA05000111 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	151.00 to 152.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	11950 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.702 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.3 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.54	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.28 m³·mol⁻¹	ChemAxon
Polarizability	12.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	120.474	31661259
DarkChem	[M-H]-	115.515	31661259
DeepCCS	[M+H]+	130.854	30932474
DeepCCS	[M-H]-	128.27	30932474
DeepCCS	[M-2H]-	164.54	30932474
DeepCCS	[M+Na]+	139.353	30932474
AllCCS	[M+H]+	125.8	32859911
AllCCS	[M+H-H2O]+	121.4	32859911
AllCCS	[M+NH4]+	129.8	32859911
AllCCS	[M+Na]+	131.0	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	139.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	2.61 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8346 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1575.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	396.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	245.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	488.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	496.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	947.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	353.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1187.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	371.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	39.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-3-Methyl-1-pentanol	CCC(C)CCO	1313.8	Standard polar	33892256
(??)-3-Methyl-1-pentanol	CCC(C)CCO	823.7	Standard non polar	33892256
(??)-3-Methyl-1-pentanol	CCC(C)CCO	840.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-3-Methyl-1-pentanol,1TMS,isomer #1	CCC(C)CCO[Si](C)(C)C	952.9	Semi standard non polar	33892256
(??)-3-Methyl-1-pentanol,1TBDMS,isomer #1	CCC(C)CCO[Si](C)(C)C(C)(C)C	1165.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-e5f5d1e7ec88b62b64cb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-23b0c8a98b639e229c8a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-36ef332a1a165815accb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-e5f5d1e7ec88b62b64cb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-23b0c8a98b639e229c8a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-3-Methyl-1-pentanol EI-B (Non-derivatized)	splash10-0a4l-9000000000-36ef332a1a165815accb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3-Methyl-1-pentanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-c39489df62ff2f126cac	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3-Methyl-1-pentanol GC-MS (1 TMS) - 70eV, Positive	splash10-0pk9-9500000000-dec6f5904aa86e1d151e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3-Methyl-1-pentanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-3-Methyl-1-pentanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 10V, Positive-QTOF	splash10-0f79-9600000000-575cd472dcd3abb8444e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 20V, Positive-QTOF	splash10-000i-9200000000-6424196dd2bfecaf076a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 40V, Positive-QTOF	splash10-0a4i-9000000000-4f8a71d2e110d724c584	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 10V, Negative-QTOF	splash10-0udi-5900000000-a912ba3330461cdae417	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 20V, Negative-QTOF	splash10-0fk9-9400000000-5321abee9dd560085ceb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 40V, Negative-QTOF	splash10-0ac0-9000000000-581579b748feaffe9001	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 10V, Negative-QTOF	splash10-0udi-0900000000-3ab02485eaffb4e83bff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 20V, Negative-QTOF	splash10-0udi-3900000000-7e863f8d55bf3ad02909	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 40V, Negative-QTOF	splash10-0006-9000000000-782427878cd74e2a75a7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 10V, Positive-QTOF	splash10-0a4r-9000000000-9efb759aea38e25e7b06	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 20V, Positive-QTOF	splash10-0a4i-9000000000-9ab1fcd9edba8359d4d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-3-Methyl-1-pentanol 40V, Positive-QTOF	splash10-0a4l-9000000000-3f04271eec170d06813d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details

Associated Disorders and Diseases

Disease References

Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]

Associated OMIM IDs

209850 (Autism)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008173

KNApSAcK ID

C00035792

Chemspider ID

11024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11508

PDB ID

Not Available

ChEBI ID

87381

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1011821

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-3-Methyl-1-pentanol (HMDB0033676)

MOL for HMDB0033676 ((±)-3-Methyl-1-pentanol)

3D MOL for HMDB0033676 ((±)-3-Methyl-1-pentanol)

3D SDF for HMDB0033676 ((±)-3-Methyl-1-pentanol)

3D-SDF for HMDB0033676 ((±)-3-Methyl-1-pentanol)

PDB for HMDB0033676 ((±)-3-Methyl-1-pentanol)

3D PDB for HMDB0033676 ((±)-3-Methyl-1-pentanol)

SMILES for HMDB0033676 ((±)-3-Methyl-1-pentanol)

INCHI for HMDB0033676 ((±)-3-Methyl-1-pentanol)

Structure for HMDB0033676 ((±)-3-Methyl-1-pentanol)

3D Structure for HMDB0033676 ((±)-3-Methyl-1-pentanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra