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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:15 UTC

Update Date

2023-02-21 17:21:56 UTC

HMDB ID

HMDB0032335

Secondary Accession Numbers

HMDB32335

Metabolite Identification

Common Name

3-Hydroxy-2-octanone

Description

3-Hydroxy-2-octanone belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 3-hydroxy-2-octanone is considered to be an oxygenated hydrocarbon. Based on a literature review a significant number of articles have been published on 3-Hydroxy-2-octanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Octanon-3-ol	HMDB
3-Hydroxyoctan-2-one	HMDB
3-(R)-Hydroxy-2-octanone	MeSH
3-Hydroxy-2-octanone	MeSH

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

3-hydroxyoctan-2-one

Traditional Name

3-hydroxyoctan-2-one

CAS Registry Number

37160-77-3

SMILES

CCCCCC(O)C(C)=O

InChI Identifier

InChI=1S/C8H16O2/c1-3-4-5-6-8(10)7(2)9/h8,10H,3-6H2,1-2H3

InChI Key

QWEHQNZGVUHHME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Monosaccharide
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000125 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032335)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032335)

Source

Endogenous

Endogenous (HMDB: HMDB0032335)

Animal

Animal (HMDB: HMDB0032335)

Exogenous

Food

Food (HMDB: HMDB0032335)

Exogenous (HMDB: HMDB0032335)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032335)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032335)

Lipid metabolism pathway (HMDB: HMDB0032335)

Cellular process

Cell signaling (HMDB: HMDB0032335)

Biochemical process

Lipid transport (HMDB: HMDB0032335)

Role

Biological role

Energy source (HMDB: HMDB0032335)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032335)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	187.00 to 188.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	11190 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.739 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.71	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.72 m³·mol⁻¹	ChemAxon
Polarizability	17.23 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]+	134.526	31661259
DarkChem	[M-H]-	130.347	31661259
DeepCCS	[M+H]+	139.214	30932474
DeepCCS	[M-H]-	136.452	30932474
DeepCCS	[M-2H]-	173.419	30932474
DeepCCS	[M+Na]+	148.241	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	134.6	32859911
AllCCS	[M+Na-2H]-	136.8	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.	4.05 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6551 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1872.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	391.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	533.5 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	567.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1074.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	375.1 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	1269.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	346.9 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	22.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-octanone	CCCCCC(O)C(C)=O	1623.1	Standard polar	33892256
3-Hydroxy-2-octanone	CCCCCC(O)C(C)=O	1043.5	Standard non polar	33892256
3-Hydroxy-2-octanone	CCCCCC(O)C(C)=O	1112.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-octanone,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C)=O	1199.1	Semi standard non polar	33892256
3-Hydroxy-2-octanone,1TMS,isomer #2	CCCCCC(O)=C(C)O[Si](C)(C)C	1324.4	Semi standard non polar	33892256
3-Hydroxy-2-octanone,1TMS,isomer #3	C=C(O[Si](C)(C)C)C(O)CCCCC	1229.8	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1384.9	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1399.7	Standard non polar	33892256
3-Hydroxy-2-octanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CCCCC)O[Si](C)(C)C	1334.1	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CCCCC)O[Si](C)(C)C	1364.6	Standard non polar	33892256
3-Hydroxy-2-octanone,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C)=O	1422.6	Semi standard non polar	33892256
3-Hydroxy-2-octanone,1TBDMS,isomer #2	CCCCCC(O)=C(C)O[Si](C)(C)C(C)(C)C	1555.4	Semi standard non polar	33892256
3-Hydroxy-2-octanone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(O)CCCCC	1446.8	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1855.5	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1788.9	Standard non polar	33892256
3-Hydroxy-2-octanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CCCCC)O[Si](C)(C)C(C)(C)C	1756.1	Semi standard non polar	33892256
3-Hydroxy-2-octanone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CCCCC)O[Si](C)(C)C(C)(C)C	1774.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-octanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-652b42925283aa582e9a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-octanone GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9100000000-e197f14af5e5bc0c4ff4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-octanone 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-Hydroxy-2-octanone 10V, Positive-QTOF	splash10-002b-1900000000-fde3ca515b98851b50f3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 20V, Positive-QTOF	splash10-00fs-9600000000-fcef0bcc965e78d965b0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 40V, Positive-QTOF	splash10-052f-9000000000-7764749361d9e24cc33c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 10V, Negative-QTOF	splash10-0006-1900000000-b0b1c8fafc09dff81671	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 20V, Negative-QTOF	splash10-0fkc-9600000000-d4955a0f91500ff0908c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 40V, Negative-QTOF	splash10-00di-9100000000-d2b68fdab5fc93009bd0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 10V, Positive-QTOF	splash10-0a59-9200000000-988f979164cd0a31b5c6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 20V, Positive-QTOF	splash10-0a5c-9100000000-02b46e0bd3497bfe6ae8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 40V, Positive-QTOF	splash10-052f-9000000000-7cd97445d72053dca4b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 10V, Negative-QTOF	splash10-0006-1900000000-06b6167c5ebb42c2bc6b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 20V, Negative-QTOF	splash10-0006-9200000000-5bd363628c4f6100ac9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-octanone 40V, Negative-QTOF	splash10-0006-9000000000-73fa0de21e8412db1e2e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009608

KNApSAcK ID

Not Available

Chemspider ID

4933945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428543

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1582401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Hydroxy-2-octanone (HMDB0032335)

MOL for HMDB0032335 (3-Hydroxy-2-octanone)

3D MOL for HMDB0032335 (3-Hydroxy-2-octanone)

3D SDF for HMDB0032335 (3-Hydroxy-2-octanone)

3D-SDF for HMDB0032335 (3-Hydroxy-2-octanone)

PDB for HMDB0032335 (3-Hydroxy-2-octanone)

3D PDB for HMDB0032335 (3-Hydroxy-2-octanone)

SMILES for HMDB0032335 (3-Hydroxy-2-octanone)

INCHI for HMDB0032335 (3-Hydroxy-2-octanone)

Structure for HMDB0032335 (3-Hydroxy-2-octanone)

3D Structure for HMDB0032335 (3-Hydroxy-2-octanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra