Cannabis Compound Database: Showing Compound Card for 1-Butanol (CDB000487)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (32)transporters (1) Show 56 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:39:41 UTC

Updated at

2020-12-07 19:07:28 UTC

CannabisDB ID

CDB000487

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

1-Butanol

Description

1-Butanol, also known as N-butan-1-ol or N-butyl alcohol, 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). Thus, 1-butanol is considered to be a fatty alcohol lipid molecule. 1-Butanol is a hydrophobic molecule, poorly soluble in water, and relatively neutral. 1-Butanol is an alcohol with a 4-carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermentation through the butanoate metabolic pathway. It has been found in Bacillus, Clostridium, Escherichia, Lactobacillus, Pseudomonas, Saccharomyces, Synechococcus and Thermoanaerobacterium ( Ref:DOI ) ( Ref:DOI ) ( Ref:DOI ). 1-Butanol is a sweet, balsam, and fruit tasting compound. In plants, 1-Butanol is found, on average, in the highest concentration in highbush blueberries and bilberries. 1-Butanol has also been detected, but not quantified in several different foods, such as napa cabbages, wild rices, red rices, bamboo shoots, and lemon verbena. 1-butanol has also been reported to be detected as a part of Cannabis sativa volatiles (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Butyl alcohol	ChEBI
1-Hydroxybutane	ChEBI
BuOH	ChEBI
N-Butan-1-ol	ChEBI
N-Butanol	ChEBI
N-Butyl alcohol	ChEBI
N-Butylalkohol	ChEBI
Propyl carbinol	ChEBI
Butan-1-ol	Kegg
Butanol	HMDB
Butyl alcohol	HMDB
Butyl hydroxide	HMDB
Hemostyp	HMDB
Methylolpropane	HMDB
Propylcarbinol	HMDB
Alcohol, N-butyl	HMDB
N Butyl alcohol	HMDB
Alcohol, butyl	HMDB
1 Butanol	HMDB
N Butanol	HMDB
1-Butanol	ChEBI

Chemical Formula

C₄H₁₀O

Average Molecular Weight

74.12

Monoisotopic Molecular Weight

74.0732

IUPAC Name

butan-1-ol

Traditional Name

butanol

CAS Registry Number

71-36-3

SMILES

CCCCO

InChI Identifier

InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

InChI Key

LRHPLDYGYMQRHN-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:28885 )
alkyl alcohol (CHEBI:28885 )
Fatty alcohols (LMFA05000109 )
a primary alcohol (BUTANOL )

Ontology

Physiological effect

Health effect:

Health condition:

Diabetes mellitus type 2

Disposition

Route of exposure:

Enteral:

Ingestion

Fibroblast

Tissue and substructures:

Epidermis

Biofluid and excreta:

Organ and components:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-89.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	63.2 mg/mL at 25 °C	Not Available
logP	0.88	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.84	ALOGPS
logP	0.81	ChemAxon
logS	0.33	ALOGPS
pKa (Strongest Acidic)	16.95	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	2	ChemAxon
Refractivity	22.13 m³·mol⁻¹	ChemAxon
Polarizability	9.21 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-061591a78bc1cdeda799	2015-03-01	View Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-f8337e5e053a4d17e4ed	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-610cf73e0b514e180dbd	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-055f-9000000000-7e23cd40dde01cb89b6f	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-f8337e5e053a4d17e4ed	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-610cf73e0b514e180dbd	Spectrum
GC-MS	1-Butanol, non-derivatized, GC-MS Spectrum	splash10-055f-9000000000-7e23cd40dde01cb89b6f	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-9000000000-b70087d61cbf63d60bd5	Spectrum
Predicted GC-MS	1-Butanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9200000000-08a8f57a90b00db3596a	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-69148177e3417cc669fd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-052f-9000000000-7ebca2648ffd63942337	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-055f-9000000000-7e23cd40dde01cb89b6f	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9000000000-53a465f38bad658bb673	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9145b21c5f3ae37774e0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-686e7cdc50d3fda3a0ff	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9000000000-53a465f38bad658bb673	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9145b21c5f3ae37774e0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-686e7cdc50d3fda3a0ff	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-61d09b30d6a547d109fc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-4d4d1c2159c658c4ee24	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-2119b542a1efb8432d12	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-61d09b30d6a547d109fc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-4d4d1c2159c658c4ee24	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-2119b542a1efb8432d12	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-4256cf8850659dacd159	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-cb6c5eeb586ac4d5655e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-21e6cc4261bed22ecbf8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-a749e449b2f26d0e75a2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b0818591ffca1f29c3ec	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d2c85c870494f5dbfc6b	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Lysosomal acid phosphatase	ACP2	11p12-p11	P11117	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Tartrate-resistant acid phosphatase type 5	ACP5	19p13.2	P13686	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
Aldehyde dehydrogenase X, mitochondrial	ALDH1B1	9p11.1	P30837	details
Sulfotransferase family cytosolic 2B member 1	SULT2B1	19q13.3	O00204	details
Sorbitol dehydrogenase	SORD	15q15.3	Q00796	details
Alcohol dehydrogenase [NADP(+)]	AKR1A1	1p33-p32	P14550	details
Alcohol dehydrogenase 4	ADH4	4q22	P08319	details
Alcohol dehydrogenase 1B	ADH1B	4q23	P00325	details
Alcohol dehydrogenase 1A	ADH1A	4q23	P07327	details
Alcohol dehydrogenase 6	ADH6	4q23	P28332	details
Beta-glucuronidase	GUSB	7q21.11	P08236	details
Plasma alpha-L-fucosidase	FUCA2	6q24	Q9BTY2	details
Trans-2-enoyl-CoA reductase, mitochondrial	MECR	1p35.3	Q9BV79	details
Lecithin retinol acyltransferase	LRAT	4q32.1	O95237	details
Nuclear receptor subfamily 1 group I member 3	NR1I3	1q23.3	Q14994	details
Zinc-binding alcohol dehydrogenase domain-containing protein 2	ZADH2	18q22.3	Q8N4Q0	details
Retinol dehydrogenase 13	RDH13	19q13.42	Q8NBN7	details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details
Fatty acyl-CoA reductase 2	FAR2	12p11.22	Q96K12	details
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Xq13.1	Q6E213	details
Testicular acid phosphatase	ACPT	19q13.4	Q9BZG2	details
Carboxylesterase 5A	CES5A	16q12.2	Q6NT32	details
Acid phosphatase-like protein 2	ACPL2	3q23	Q8TE99	details
Synaptic vesicle membrane protein VAT-1 homolog-like	VAT1L	16q23.1	Q9HCJ6	details
Quinone oxidoreductase PIG3	TP53I3	2p23.3	Q53FA7	details
Synaptic vesicle membrane protein VAT-1 homolog	VAT1	17q21	Q99536	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
Sorbitol dehydrogenase	SORD	15q15.3	Q00796	details
Alcohol dehydrogenase 4	ADH4	4q22	P08319	details
Alcohol dehydrogenase 1B	ADH1B	4q23	P00325	details
Alcohol dehydrogenase 1A	ADH1A	4q23	P07327	details
Alcohol dehydrogenase 6	ADH6	4q23	P28332	details
Trans-2-enoyl-CoA reductase, mitochondrial	MECR	1p35.3	Q9BV79	details
Nuclear receptor subfamily 1 group I member 3	NR1I3	1q23.3	Q14994	details
Zinc-binding alcohol dehydrogenase domain-containing protein 2	ZADH2	18q22.3	Q8N4Q0	details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details
Synaptic vesicle membrane protein VAT-1 homolog-like	VAT1L	16q23.1	Q9HCJ6	details
Quinone oxidoreductase PIG3	TP53I3	2p23.3	Q53FA7	details
Synaptic vesicle membrane protein VAT-1 homolog	VAT1	17q21	Q99536	details
Reticulon-4-interacting protein 1, mitochondrial	RTN4IP1	6q21	Q8WWV3	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 3	NR1I3	1q23.3	Q14994	details
Klotho	KL	13q12	Q9UEF7	details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor subfamily 1 group I member 3	NR1I3	1q23.3	Q14994	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0004327

DrugBank ID

DB02145

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

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 ]

Only showing the first 10 proteins. There are 56 proteins in total.

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Enzymes

Enzyme Details

1. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

Enzyme Details

2. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Enzyme Details

3. Serum paraoxonase/arylesterase 2

General function:: Involved in arylesterase activity
Specific function:: Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:: PON2
Uniprot ID:: Q15165
Molecular weight:: 39380.535

Enzyme Details

4. Intestinal-type alkaline phosphatase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ALPI
Uniprot ID:: P09923
Molecular weight:: 56811.695

Enzyme Details

5. Lysosomal acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Not Available
Gene Name:: ACP2
Uniprot ID:: P11117
Molecular weight:: 48343.92

Enzyme Details

6. Alkaline phosphatase, tissue-nonspecific isozyme

General function:: Involved in catalytic activity
Specific function:: This isozyme may play a role in skeletal mineralization.
Gene Name:: ALPL
Uniprot ID:: P05186
Molecular weight:: 57304.435

Enzyme Details

7. Tartrate-resistant acid phosphatase type 5

General function:: Involved in hydrolase activity
Specific function:: Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:: ACP5
Uniprot ID:: P13686
Molecular weight:: 36598.47

Enzyme Details

8. Alkaline phosphatase, placental-like

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ALPPL2
Uniprot ID:: P10696
Molecular weight:: 57376.515

Enzyme Details

9. Aldehyde dehydrogenase X, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Enzyme Details

10. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Transporters

Enzyme Details

1. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Only showing the first 10 proteins. There are 56 proteins in total.

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Showing Compound Card for 1-Butanol (CDB000487)

Structure for CDB000487 (1-Butanol)

Enzymes

Transporters