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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:06 UTC

Update Date

2023-02-21 17:19:48 UTC

HMDB ID

HMDB0030966

Secondary Accession Numbers

HMDB30966

Metabolite Identification

Common Name

(3xi,5Z)-1,5-Octadien-3-ol

Description

(3xi,5Z)-1,5-Octadien-3-ol, also known as octa-1,5-dien-3-ol, 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, (3XI,5Z)-1,5-octadien-3-ol is considered to be a fatty alcohol. Based on a literature review a significant number of articles have been published on (3xi,5Z)-1,5-Octadien-3-ol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Octa-1,5-dien-3-ol, (e)-isomer	MeSH
Octa-1,5-dien-3-ol	MeSH
(5Z)-1,5-Octadien-3-ol	HMDB
(Z)-1,5-Octadien-3-ol	HMDB
1,5Z-Octadien-3R-ol	HMDB
Z-1,5-Octadien-3-ol	HMDB

Chemical Formula

C₈H₁₄O

Average Molecular Weight

126.1962

Monoisotopic Molecular Weight

126.10446507

IUPAC Name

(5E)-octa-1,5-dien-3-ol

Traditional Name

(5E)-octa-1,5-dien-3-ol

CAS Registry Number

50306-18-8

SMILES

CC\C=C\CC(O)C=C

InChI Identifier

InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4-6,8-9H,2-3,7H2,1H3/b6-5+

InChI Key

APFBWMGEGSELQP-AATRIKPKSA-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
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty alcohols (LMFA05000488 )

Ontology

Physiological effect

Organoleptic effect

Odor

Earthy

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0030966)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030966)

Source

Endogenous

Endogenous (HMDB: HMDB0030966)

Animal

Animal (HMDB: HMDB0030966)

Exogenous

Food

Food (HMDB: HMDB0030966)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Exogenous (HMDB: HMDB0030966)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030966)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030966)

Lipid metabolism pathway (HMDB: HMDB0030966)

Cellular process

Cell signaling (HMDB: HMDB0030966)

Biochemical process

Lipid transport (HMDB: HMDB0030966)

Role

Biological role

Energy source (HMDB: HMDB0030966)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030966)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	185.00 to 186.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2853 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.192 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.54 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.12	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	17.44	ChemAxon
pKa (Strongest Basic)	-1.7	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	4	ChemAxon
Refractivity	41.29 m³·mol⁻¹	ChemAxon
Polarizability	15.49 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]+	132.001	31661259
DarkChem	[M-H]-	127.761	31661259
DeepCCS	[M+H]+	128.85	30932474
DeepCCS	[M-H]-	125.541	30932474
DeepCCS	[M-2H]-	162.592	30932474
DeepCCS	[M+Na]+	137.603	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	132.4	32859911
AllCCS	[M+Na-2H]-	135.1	32859911
AllCCS	[M+HCOO]-	138.1	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.	4.02 minutes	32390414
Predicted by Siyang on May 30, 2022	12.023 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1833.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	133.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	446.3 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	434.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1056.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	384.1 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	1088.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	349.4 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	10.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3xi,5Z)-1,5-Octadien-3-ol	CC\C=C\CC(O)C=C	1461.6	Standard polar	33892256
(3xi,5Z)-1,5-Octadien-3-ol	CC\C=C\CC(O)C=C	928.5	Standard non polar	33892256
(3xi,5Z)-1,5-Octadien-3-ol	CC\C=C\CC(O)C=C	986.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3xi,5Z)-1,5-Octadien-3-ol,1TMS,isomer #1	C=CC(C/C=C/CC)O[Si](C)(C)C	1068.6	Semi standard non polar	33892256
(3xi,5Z)-1,5-Octadien-3-ol,1TBDMS,isomer #1	C=CC(C/C=C/CC)O[Si](C)(C)C(C)(C)C	1284.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-58d0b25b136c6c3c636a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00tu-9400000000-3bf279bd8d563a8df3c7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 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 - (3xi,5Z)-1,5-Octadien-3-ol 10V, Positive-QTOF	splash10-0a6r-1900000000-413227a83e5e4b9e3816	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 20V, Positive-QTOF	splash10-0a4i-9800000000-1166471bb3a978d659e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 40V, Positive-QTOF	splash10-0ldl-9000000000-31ffcee9a40bd841e98d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 10V, Negative-QTOF	splash10-004i-0900000000-9182ecd405b37bc7b8ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 20V, Negative-QTOF	splash10-004i-3900000000-c2ef89363d8a8b217a50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 40V, Negative-QTOF	splash10-0a4i-9100000000-1b79a0c1dcecb780d838	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 10V, Negative-QTOF	splash10-004i-0900000000-b08da4d2091aa16d3bd8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 20V, Negative-QTOF	splash10-0a6s-9400000000-1c65b9507408967f87cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 40V, Negative-QTOF	splash10-0pvi-9000000000-4209ccf0113e0e141b88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 10V, Positive-QTOF	splash10-014l-9000000000-6021fedfc1a532e08e56	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 20V, Positive-QTOF	splash10-05o3-9000000000-ef503b21b08e92973908	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,5Z)-1,5-Octadien-3-ol 40V, Positive-QTOF	splash10-067i-9000000000-d7fd09428c6b688287f7	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB002953

KNApSAcK ID

C00053585

Chemspider ID

4933972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428570

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028101

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (3xi,5Z)-1,5-Octadien-3-ol (HMDB0030966)

MOL for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

3D MOL for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

3D SDF for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

3D-SDF for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

PDB for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

3D PDB for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

SMILES for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

INCHI for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

Structure for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

3D Structure for HMDB0030966 ((3xi,5Z)-1,5-Octadien-3-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra