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Showing NP-Card for Isopropyl alcohol (NP0001488)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-17 17:03:41 UTC
NP-MRD IDNP0001488
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsopropyl alcohol
DescriptionIsopropyl alcohol, also known as isopropanol or 1-methylethanol, 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). It is used in the manufacture of acetone and its derivatives and as a solvent. Isopropyl alcohol exists in all living species, ranging from bacteria to humans. Isopropyl alcohol is an alcohol, bitter, and musty tasting compound. Isopropyl alcohol has also been detected, but not quantified in several different foods, such as papaya, roselles, apples, sweet cherries, and allium (onion). Isopropyl alcohol is an isomer of 1-propanol and is considered as a potentially toxic compound. Topically, it is used as an antiseptic. It is a colorless liquid having disinfectant properties.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001488 (Isopropyl alcohol)


  Mrv1652303202019002D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
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3D MOL for NP0001488 (Isopropyl alcohol)

HMDB0000863
     RDKit          3D
Isopropyl alcohol
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.3264    0.0892   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020    0.5308   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562   -0.7193   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541    1.4213    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411    0.8325    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -0.8179    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -0.2461   -0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579    1.0622   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409   -1.6494   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -0.7309    0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -0.7828   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    1.0103    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
Download

3D SDF for NP0001488 (Isopropyl alcohol)


  Mrv1652303202019002D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3

> <INCHI_KEY>
KFZMGEQAYNKOFK-UHFFFAOYSA-N

> <FORMULA>
C3H8O

> <MOLECULAR_WEIGHT>
60.095

> <EXACT_MASS>
60.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
7.1373816572351085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propan-2-ol

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.2548059106666668

> <ALOGPS_LOGS>
0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.262586277858762

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8091447620645766

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
17.4287

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopropyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001488 (Isopropyl alcohol)

HMDB0000863
     RDKit          3D
Isopropyl alcohol
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.3264    0.0892   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020    0.5308   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562   -0.7193   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541    1.4213    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411    0.8325    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -0.8179    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -0.2461   -0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579    1.0622   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409   -1.6494   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -0.7309    0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -0.7828   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    1.0103    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
Download

PDB for NP0001488 (Isopropyl alcohol)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for NP0001488 (Isopropyl alcohol)

COMPND    HMDB0000863
HETATM    1  C1  UNL     1       1.326   0.089  -0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.102   0.531  -0.235  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.956  -0.719  -0.242  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.554   1.421   0.718  1.00  0.00           O  
HETATM    5  H1  UNL     1       1.941   0.833   0.507  1.00  0.00           H  
HETATM    6  H2  UNL     1       1.293  -0.818   0.651  1.00  0.00           H  
HETATM    7  H3  UNL     1       1.720  -0.246  -0.982  1.00  0.00           H  
HETATM    8  H4  UNL     1      -0.158   1.062  -1.221  1.00  0.00           H  
HETATM    9  H5  UNL     1      -0.341  -1.649  -0.237  1.00  0.00           H  
HETATM   10  H6  UNL     1      -1.576  -0.731   0.685  1.00  0.00           H  
HETATM   11  H7  UNL     1      -1.604  -0.783  -1.135  1.00  0.00           H  
HETATM   12  H8  UNL     1      -0.990   1.010   1.493  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4    8
CONECT    3    9   10   11
CONECT    4   12
END
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SMILES for NP0001488 (Isopropyl alcohol)

CC(C)O
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INCHI for NP0001488 (Isopropyl alcohol)

InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
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View in JSmol
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 Mass60.0950 Da
Monoisotopic Mass60.05751 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepa L.FooDB
    • J. F. Carson and Francis F. Wong. The Volatile Flavor Components of Onions. J. Agric. Food Chem. ...
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Asparagus officinalisKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. botrytisFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carica papayaKNApSAcK Database
Carica papaya L.FooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiifoliaPlant
Citrus aurantiumKNApSAcK Database
Citrus grandisKNApSAcK Database
Citrus hystrixKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus maximaPlant
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Hibiscus sabbariffaFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-83.00 to -81.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point82.00 to 83.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP0.05Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility378 g/LALOGPS
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
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
Good Scents IDrw1007401
References
General References
  1. Lindberg M, Farm G, Scheynius A: Differential effects of sodium lauryl sulphate and non-anoic acid on the expression of CD1a and ICAM-1 in human epidermis. Acta Derm Venereol. 1991;71(5):384-8. [PubMed:1684465 ]
  2. Lee CK, Ho PL, Chan NK, Mak A, Hong J, Lin CK: Impact of donor arm skin disinfection on the bacterial contamination rate of platelet concentrates. Vox Sang. 2002 Oct;83(3):204-8. [PubMed:12366760 ]
  3. Specht C, Stoye I, Muller-Goymann CC: Comparative investigations to evaluate the use of organotypic cultures of transformed and native dermal and epidermal cells for permeation studies. Eur J Pharm Biopharm. 1998 Nov;46(3):273-8. [PubMed:9885298 ]
  4. Zesch A, Schaefer H: [On interactions of drugs on and in the skin/comparative studies on the mutual influences of ethyleneglycol-monosalicylate and benzylnicotinate (author's transl)]. Derm Beruf Umwelt. 1981;29(6):161-7. [PubMed:7338200 ]
  5. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of 1-Chloro-2-propanol (Technical Grade) (CAS NO. 127-00-4) in F344/N Rats and B6C3F1 Mice (Drinking Water Studies. Natl Toxicol Program Tech Rep Ser. 1998 Sep;477:1-264. [PubMed:12571686 ]
  6. Liu P, Bergstrom TK: Quantitative evaluation of aqueous isopropyl alcohol enhancement on skin flux of terbutaline (sulfate). 2. Permeability contributions of equilibrated drug species across human skin in vitro. J Pharm Sci. 1996 Mar;85(3):320-5. [PubMed:8699337 ]
  7. Froman RD, Owen SV, Murphy C: Isopropyl pad use in neonatal intensive care units. J Perinatol. 1998 May-Jun;18(3):216-20. [PubMed:9659653 ]
  8. Bailey DG, Wilson TW, Johnson GE: A gas chromatographic method for measuring 6-mercaptopurine in serum. J Chromatogr. 1975 Sep 3;111(2):305-11. [PubMed:1159009 ]
  9. Abdashirova NF: [Peculiarities of alternations in free radical oxidation in blood of humans contacting ozone at work]. Aviakosm Ekolog Med. 1999;33(1):38-41. [PubMed:10330571 ]
  10. Wittmann S, Gilg T, Dietz HG, Grantzow R, Peschel O, von Meyer L: [Isopropanol and acetone level in serum after preoperative surface disinfection with antiseptics containing isopropanol]. Blutalkohol. 1992 Sep;29(5):326-35. [PubMed:1389018 ]
  11. Anderson LM, Koseniauskas R, Burak ES, Moskal TJ, Gombar CT, Phillips JM, Sansone EB, Keimig S, Magee PN, Rice JM, et al.: Reduced blood clearance and increased urinary excretion of N-nitrosodimethylamine in patas monkeys exposed to ethanol or isopropyl alcohol. Cancer Res. 1992 Mar 15;52(6):1463-8. [PubMed:1540953 ]
  12. Jones AE, Summers RL: Detection of isopropyl alcohol in a patient with diabetic ketoacidosis. J Emerg Med. 2000 Aug;19(2):165-8. [PubMed:10903466 ]
  13. Dumollard C, Wiart JF, Hakim F, Demarly C, Morbidelli P, Allorge D, Gaulier JM: Putatively lethal ingestion of isopropyl alcohol-related case: interpretation of post mortem isopropyl alcohol and acetone concentrations remains challenging. Int J Legal Med. 2021 Jan;135(1):175-182. doi: 10.1007/s00414-020-02444-4. Epub 2020 Oct 22. [PubMed:33090260 ]