Record Information
Version1.0
Created at2020-03-19 00:53:49 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000734
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsopropyl alcohol
DescriptionIsopropyl alcohol, also known as isopropanol, rubbing alcohol or IPA, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R, R'=alkyl, aryl). Isopropanol is the simplest example of a secondary alcohol, where the alcohol carbon is attached to two other carbons sometimes shown as (CH3)2CHOH. It is a structural isomer of 1-propanol. Isopropanol is a colorless, flammable liquid with a strong odor. It is miscible in water, ethanol, ether, and chloroform. Isoproanol is produced industrially via the hydrogenation of acetone or the hydration of propene with water. It is widely used as a solvent for coatings, as a cleaning fluid (for eyeglasses and electrical contacts) and as a solvent for household or personal care products such as antiseptics, disinfectants, and detergents. Isopropanol has an alcoholic, musty or woody aroma and a similar woody or musty taste. Isopropanol is an approved food additive and is used in cosmetics as an antifoaming agent, a perfuming agent and a viscosity controlling agent. It is frequently used as an extraction solvent in food preparation. Isopropanol is also naturally present in apple, cognac, roselle fruit and papaya (Carica papaya) and contributes to their distinct odor. Isopropanol and its metabolite, acetone, act as central nervous system (CNS) depressants (PMID: 24815348 ). It is oxidized to form acetone by alcohol dehydrogenase in the liver (PMID: 12726989 ). Unlike methanol or ethylene glycol poisoning, the metabolites of isopropanol are considerably less toxic, and treatment is largely supportive. Isopropanol is found in trace amounts from extracted plant essential oil. As a result, it can be found in hemp, CBD or cannabis oils.
Structure
Thumb
Synonyms
ValueSource
1-MethylethanolChEBI
1-Methylethyl alcoholChEBI
2-HydroxypropaneChEBI
2-PropanolChEBI
I-propanolChEBI
I-propylalkoholChEBI
IPAChEBI
IsopropanolChEBI
IsopropylalkoholChEBI
Sec-propanolChEBI
IsoproKegg
2-Propyl alcoholHMDB
AlcojelHMDB
AlkolaveHMDB
AvantinHMDB
AvantineHMDB
HartosolHMDB
LavacoHMDB
PetroholHMDB
TakineocolHMDB
Alcohol, isopropylHMDB
Alcohol, rubbingHMDB
Rubbing alcoholHMDB
2 PropanolHMDB
ISOPROPYL alcoholChEBI
Chemical FormulaC3H8O
Average Molecular Weight60.1
Monoisotopic Molecular Weight60.0575
IUPAC Namepropan-2-ol
Traditional Nameisopropyl alcohol
CAS Registry Number67-63-0
SMILES
CC(C)O
InChI Identifier
InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
InChI KeyKFZMGEQAYNKOFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point82.6 °CWikipedia
Water Solubility1000 mg/mLNot Available
logP0.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.04ALOGPS
logP0.25ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)17.26ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.43 m³·mol⁻¹ChemAxon
Polarizability7.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-8f0393a68e54e56686382014-09-20View Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-b56f808ef55c854e8324Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-f68d78a99d0ee77081c8Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-a1c27780d39325f67c84Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-40a45591af6378500aebSpectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-2261ea7d03d835d46644Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-3c81c56ab53eb5aaa2ecSpectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-7936ed4d93d5699b0366Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-b56f808ef55c854e8324Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-f68d78a99d0ee77081c8Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-a1c27780d39325f67c84Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-40a45591af6378500aebSpectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-2261ea7d03d835d46644Spectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-3c81c56ab53eb5aaa2ecSpectrum
GC-MSIsopropyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-7936ed4d93d5699b0366Spectrum
Predicted GC-MSIsopropyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-026d02184beec46b90ccSpectrum
Predicted GC-MSIsopropyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-010c-9200000000-82e9183374d718888481Spectrum
Predicted GC-MSIsopropyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsopropyl alcohol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-958007b112253f530fa12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dl-9000000000-eec0fd84c38e3cc2fb7d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-e524005ac3e29f5e6e602012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0002-9000000000-b56f808ef55c854e83242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0002-9000000000-2261ea7d03d835d466442012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0002-9000000000-3c81c56ab53eb5aaa2ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0002-9000000000-7936ed4d93d5699b03662012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-52e1a906e58615d920fd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-e66cba449fc3e39cabcb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-34d2b3ce7e4949d6207e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-06d1878fb0f08269b0402015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-a3c0cec1f0523a5089d62015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b7cef7808f5c6bfd85c92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-28b1a4f33a69b25b3b122021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-28b1a4f33a69b25b3b122021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c6a8f10b148e0b66c2de2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5381c9dfee7dd1735ffd2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-469388653449614be2852021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8d43c0c81442679649372021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2, membrane associatedPLA2G2A1p35P14555 details
Serum paraoxonase/lactonase 3PON37q21.3Q15166 details
Serum paraoxonase/arylesterase 1PON17q21.3P27169 details
Serum paraoxonase/arylesterase 2PON27q21.3Q15165 details
Intestinal-type alkaline phosphataseALPI2q37.1P09923 details
Lysosomal acid phosphataseACP211p12-p11P11117 details
Alkaline phosphatase, tissue-nonspecific isozymeALPL1p36.12P05186 details
Tartrate-resistant acid phosphatase type 5ACP519p13.2P13686 details
Alkaline phosphatase, placental-likeALPPL22q37P10696 details
Peroxiredoxin-6PRDX61q25.1P30041 details
Aldehyde dehydrogenase X, mitochondrialALDH1B19p11.1P30837 details
L-xylulose reductaseDCXR17q25.3Q7Z4W1 details
Sulfotransferase family cytosolic 2B member 1SULT2B119q13.3O00204 details
Ribonuclease pancreaticRNASE114q11.2P07998 details
Sorbitol dehydrogenaseSORD15q15.3Q00796 details
Alcohol dehydrogenase [NADP(+)]AKR1A11p33-p32P14550 details
Alcohol dehydrogenase 4ADH44q22P08319 details
AdenosylhomocysteinaseAHCY20q11.22P23526 details
Alcohol dehydrogenase 1BADH1B4q23P00325 details
Alcohol dehydrogenase 1AADH1A4q23P07327 details
Alcohol dehydrogenase 6ADH64q23P28332 details
Beta-glucuronidaseGUSB7q21.11P08236 details
Plasma alpha-L-fucosidaseFUCA26q24Q9BTY2 details
GTP cyclohydrolase 1GCH114q22.1-q22.2P30793 details
Trans-2-enoyl-CoA reductase, mitochondrialMECR1p35.3Q9BV79 details
Chitotriosidase-1CHIT1Q13231 details
Ganglioside GM2 activatorGM2A5q33.1P17900 details
Lecithin retinol acyltransferaseLRAT4q32.1O95237 details
Tumor necrosis factorTNF6p21.3P01375 details
Nuclear receptor subfamily 1 group I member 3NR1I31q23.3Q14994 details
Zinc-binding alcohol dehydrogenase domain-containing protein 2ZADH218q22.3Q8N4Q0 details
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
Fatty acyl-CoA reductase 2FAR212p11.22Q96K12 details
Acyl-CoA wax alcohol acyltransferase 2AWAT2Xq13.1Q6E213 details
Testicular acid phosphataseACPT19q13.4Q9BZG2 details
Carboxylesterase 5ACES5A16q12.2Q6NT32 details
Spliceosome RNA helicase DDX39BDDX39B6p21.3Q13838 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
Acid phosphatase-like protein 2ACPL23q23Q8TE99 details
Synaptic vesicle membrane protein VAT-1 homolog-likeVAT1L16q23.1Q9HCJ6 details
Quinone oxidoreductase PIG3TP53I32p23.3Q53FA7 details
Synaptic vesicle membrane protein VAT-1 homologVAT117q21Q99536 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Serum paraoxonase/arylesterase 1PON17q21.3P27169 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2, membrane associatedPLA2G2A1p35P14555 details
Serum paraoxonase/lactonase 3PON37q21.3Q15166 details
Serum paraoxonase/arylesterase 2PON27q21.3Q15165 details
Intestinal-type alkaline phosphataseALPI2q37.1P09923 details
Alkaline phosphatase, tissue-nonspecific isozymeALPL1p36.12P05186 details
Alkaline phosphatase, placental-likeALPPL22q37P10696 details
Sorbitol dehydrogenaseSORD15q15.3Q00796 details
Alcohol dehydrogenase 4ADH44q22P08319 details
Alcohol dehydrogenase 1BADH1B4q23P00325 details
Alcohol dehydrogenase 1AADH1A4q23P07327 details
Alcohol dehydrogenase 6ADH64q23P28332 details
Trans-2-enoyl-CoA reductase, mitochondrialMECR1p35.3Q9BV79 details
Nuclear receptor subfamily 1 group I member 3NR1I31q23.3Q14994 details
Zinc-binding alcohol dehydrogenase domain-containing protein 2ZADH218q22.3Q8N4Q0 details
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
Synaptic vesicle membrane protein VAT-1 homolog-likeVAT1L16q23.1Q9HCJ6 details
Quinone oxidoreductase PIG3TP53I32p23.3Q53FA7 details
Synaptic vesicle membrane protein VAT-1 homologVAT117q21Q99536 details
Reticulon-4-interacting protein 1, mitochondrialRTN4IP16q21Q8WWV3 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Tumor necrosis factorTNF6p21.3P01375 details
Nuclear receptor subfamily 1 group I member 3NR1I31q23.3Q14994 details
KlothoKL13q12Q9UEF7 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
mRNA-capping enzymeRNGTT6q16O60942 details
Nuclear receptor subfamily 1 group I member 3NR1I31q23.3Q14994 details
Spliceosome RNA helicase DDX39BDDX39B6p21.3Q13838 details
Concentrations Data
Not Available
HMDB IDHMDB0000863
DrugBank IDDB02325
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008282
KNApSAcK IDC00048438
Chemspider ID3644
KEGG Compound IDC01845
BioCyc IDISO-PROPANOL
BiGG IDNot Available
Wikipedia LinkIsopropyl_Alcohol
METLIN ID4192
PubChem Compound3776
PDB IDNot Available
ChEBI ID17824
References
General References
  1. Slaughter RJ, Mason RW, Beasley DM, Vale JA, Schep LJ: Isopropanol poisoning. Clin Toxicol (Phila). 2014 Jun;52(5):470-8. doi: 10.3109/15563650.2014.914527. Epub 2014 May 9. [PubMed:24815348 ]
  2. Kalapos MP: On the mammalian acetone metabolism: from chemistry to clinical implications. Biochim Biophys Acta. 2003 May 2;1621(2):122-39. doi: 10.1016/s0304-4165(03)00051-5. [PubMed:12726989 ]

Only showing the first 10 proteins. There are 69 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
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
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
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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
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
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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715

Transporters

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 69 proteins in total.