Cannabis Compound Database: Showing Compound Card for 1-Undecanol (CDB000492)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5)transporters (1) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:39:55 UTC

Updated at

2020-12-07 19:07:28 UTC

CannabisDB ID

CDB000492

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

1-Undecanol

Description

1-Undecanol, also known as N-undecyl alcohol or undecan-1-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, 1-undecanol is considered to be a fatty alcohol lipid molecule. 1-Undecanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Undecanol is a colorless, water-insoluble liquid. It has a floral citrus like odor, and a fatty taste and is used as a flavoring ingredient in foods. 1-Undecanol can be found in fruits including apples and bananas. 1-Undecanol is a volatile component of cannabis (PMID: 26657499 ) and, as such, it can also be detected as constituent of marijuana smoke and is volatilized during the combustion of cannabis (marijuana) ( Ref:DOI ). It is commonly produced by the reduction of 1-undecanal, the analogous aldehyde.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Hendecanoic alcohol	ChEBI
N-Hendecylenic alcohol	ChEBI
N-Undecyl alcohol	ChEBI
Undecan-1-ol	ChEBI
Undecyl alcohol	ChEBI
1-Hendecanol	HMDB
1-Undecyl alcohol	HMDB
Alcohol c-11	HMDB
Alcohol C11	HMDB
C11 Alcohol	HMDB
Decyl carbinol	HMDB
Dlcohol c-11 undecylic	HMDB
Fatty alcohol(C11)	HMDB
Hendecanol	HMDB
Hendecyl alcohol	HMDB
N-Undecan-1-ol	HMDB
N-Undecanol	HMDB
Neodol 1	HMDB
Neoflex 11	HMDB
Pri-N-undecyl alcohol	HMDB
Tip-nip	HMDB
UMQ	HMDB
UNA	HMDB
Undecanol-(1)	HMDB

Chemical Formula

C₁₁H₂₄O

Average Molecular Weight

172.31

Monoisotopic Molecular Weight

172.1827

IUPAC Name

undecan-1-ol

Traditional Name

undecanol

CAS Registry Number

112-42-5

SMILES

CCCCCCCCCCCO

InChI Identifier

InChI=1S/C11H24O/c1-2-3-4-5-6-7-8-9-10-11-12/h12H,2-11H2,1H3

InChI Key

KJIOQYGWTQBHNH-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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:87499 )
fatty alcohol (CHEBI:87499 )
Fatty alcohols (LMFA05000144 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	19 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.83	ALOGPS
logP	3.92	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	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	9	ChemAxon
Refractivity	54.34 m³·mol⁻¹	ChemAxon
Polarizability	23.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-a4908a99a95a5a1b998b	2015-03-01	View Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-7e5203a4c36f0f292fbf	Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-a674e00407a29d9f0246	Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-20374066c5383835f838	Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-7e5203a4c36f0f292fbf	Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-a674e00407a29d9f0246	Spectrum
GC-MS	1-Undecanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-20374066c5383835f838	Spectrum
Predicted GC-MS	1-Undecanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01w1-9300000000-637e09ce634220d50bc6	Spectrum
Predicted GC-MS	1-Undecanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-9310000000-6b216fc35c8f2a25e9c3	Spectrum
Predicted GC-MS	1-Undecanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0900000000-8ebeeb6969498275eacc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-7c23974882f2ff7bf9b7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-9777b968953b0fa7040c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-b09a5b215289c958a646	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-e1392129917c2f794c33	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-30f040bbc0f5cc2adcf3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-5ba8abcfca58b4289f2a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-4be1565d7d285ae7e142	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9300000000-57ab5b37047eedc6f2c7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-9100000000-f1f929d2dcecb1486a99	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-f85138510f67712bf1bc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-b4a14c511d1518a416df	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkyldihydroxyacetonephosphate synthase, peroxisomal	AGPS	2q31.2	O00116	details
Fatty acyl-CoA reductase 1	FAR1	11p15.2	Q8WVX9	details
Fatty acyl-CoA reductase 2	FAR2	12p11.22	Q96K12	details
Acyl-CoA wax alcohol acyltransferase 1	AWAT1	Xq13.1	Q58HT5	details
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Xq13.1	Q6E213	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Platelet glycoprotein 4	CD36	7q11.2	P16671	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Free fatty acid receptor 1	FFAR1	19q13.1	O14842	details
Free fatty acid receptor 4	FFAR4	10q23.33	Q5NUL3	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0013113

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002917

KNApSAcK ID

C00019556

Chemspider ID

7892

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Undecanol

METLIN ID

Not Available

PubChem Compound

8184

PDB ID

Not Available

ChEBI ID

87499

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details

1. Alkyldihydroxyacetonephosphate synthase, peroxisomal

General function:: Involved in catalytic activity
Specific function:: 1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
Gene Name:: AGPS
Uniprot ID:: O00116
Molecular weight:: 72911.2

Enzyme Details

2. Fatty acyl-CoA reductase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reduction of saturated fatty acyl-CoA with chain length C16 or C18 to fatty alcohols.
Gene Name:: FAR1
Uniprot ID:: Q8WVX9
Molecular weight:: 59356.25

Enzyme Details

3. Fatty acyl-CoA reductase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:: FAR2
Uniprot ID:: Q96K12
Molecular weight:: 59437.92

Enzyme Details

4. Acyl-CoA wax alcohol acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:: AWAT1
Uniprot ID:: Q58HT5
Molecular weight:: 37758.815

Enzyme Details

5. Acyl-CoA wax alcohol acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:: AWAT2
Uniprot ID:: Q6E213
Molecular weight:: 38093.25

Transporters

Enzyme Details

1. Platelet glycoprotein 4

General function:: Not Available
Specific function:: Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:: CD36
Uniprot ID:: P16671
Molecular weight:: 53054.0

Showing Compound Card for 1-Undecanol (CDB000492)

Structure for CDB000492 (1-Undecanol)

Enzymes

Transporters