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Showing NP-Card for Propyl alcohol (NP0000995)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-17 16:52:15 UTC
NP-MRD IDNP0000995
Secondary Accession NumbersNone
Natural Product Identification
Common NamePropyl alcohol
DescriptionPropyl alcohol, also known as 1-propanol, n-propanol, or simply propanol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds in which a hydroxy group is bonded to a primary carbon, with the general structure RCOH (R=alkyl, aryl). Propyl alcohol is a colourless, volatile liquid that is fully miscible with water. It has a sweet odour and an alcoholic, fermented, fusel taste. Propyl alcohol exists in all living species, ranging from bacteria to plants to humans. Propanol can be produced through fermentation of sugars by bacteria and yeast and small amounts are produced by gut microflora. Propanol has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ). When ingested, 1-propanol is metabolized by alcohol dehydrogenase to propionic acid leading to metabolic acidosis and an elevated anion gap (PMID: 18375643 ). It can be found in small amounts in alcoholic beverages such as wine. Industrially, the major use of 1-propanol is as a solvent as well as an intermediate in forming other industrially important compounds. It is used as a carrier and extraction solvent for natural products, such as flavourings, vegetable oils, resins, waxes, and gums, and as a solvent for synthetic polymers, such as polyvinyl butyral, cellulose esters, lacquers, and PVC adhesives. Other solvent applications include the use of 1-propanol in the polymerization and spinning of acrylonitrile, in flexographic printing inks, and in the dyeing of wool. 1-Propanol is used for both its solvent and antiseptic properties in drugs and cosmetics, such as lotions, soaps, and nail polishes (IPCS INCHEM, EHC 102). Both 1-propanol and 2-propanol are often used in hand disinfectants as they have excellent bactericidal activity. 1-Propanol is used less in industry than 2-propanol as it is more expensive and it is a toxicant that has a similar taste to ethanol, so 2-propanol is used as its unpleasant smell discourages abuse.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000995 (Propyl alcohol)


  Mrv1652303202018592D          

  4  3  0  0  0  0            999 V2000
    2.0625   -0.7145    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
    0.8250    0.0000    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
  3  4  1  0  0  0  0
M  END
Download

3D MOL for NP0000995 (Propyl alcohol)

HMDB0000820
     RDKit          3D
Propyl alcohol
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.9495    0.8106   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -0.5404    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.5307    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746   -0.3369   -0.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    1.1298   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610    1.5123    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8398    0.7757   -1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919   -1.2979   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063   -0.7348    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -1.4883    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1452    0.3128    1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239    0.3879   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
Download

3D SDF for NP0000995 (Propyl alcohol)


  Mrv1652303202018592D          

  4  3  0  0  0  0            999 V2000
    2.0625   -0.7145    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
    0.8250    0.0000    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
  3  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCO

> <INCHI_IDENTIFIER>
InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3

> <INCHI_KEY>
BDERNNFJNOPAEC-UHFFFAOYSA-N

> <FORMULA>
C3H8O

> <MOLECULAR_WEIGHT>
60.095

> <EXACT_MASS>
60.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
7.234838991701065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propan-1-ol

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.3607532809999999

> <ALOGPS_LOGS>
0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.846621484175344

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9910877628217039

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
17.5339

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propanol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000995 (Propyl alcohol)

HMDB0000820
     RDKit          3D
Propyl alcohol
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.9495    0.8106   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -0.5404    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.5307    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746   -0.3369   -0.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    1.1298   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610    1.5123    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8398    0.7757   -1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919   -1.2979   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063   -0.7348    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -1.4883    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1452    0.3128    1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239    0.3879   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
Download

PDB for NP0000995 (Propyl 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       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   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                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for NP0000995 (Propyl alcohol)

COMPND    HMDB0000820
HETATM    1  C1  UNL     1      -0.949   0.811  -0.389  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.635  -0.540   0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.871  -0.531   0.505  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.475  -0.337  -0.756  1.00  0.00           O  
HETATM    5  H1  UNL     1      -0.077   1.130  -0.977  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.161   1.512   0.456  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.840   0.776  -1.045  1.00  0.00           H  
HETATM    8  H4  UNL     1      -0.892  -1.298  -0.525  1.00  0.00           H  
HETATM    9  H5  UNL     1      -1.206  -0.735   1.143  1.00  0.00           H  
HETATM   10  H6  UNL     1       1.146  -1.488   0.958  1.00  0.00           H  
HETATM   11  H7  UNL     1       1.145   0.313   1.162  1.00  0.00           H  
HETATM   12  H8  UNL     1       2.124   0.388  -0.756  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    8    9
CONECT    3    4   10   11
CONECT    4   12
END
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SMILES for NP0000995 (Propyl alcohol)

CCCO
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INCHI for NP0000995 (Propyl alcohol)

InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
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View in JSmol
Synonyms
ValueSource
1-HydroxypropaneChEBI
1-PropanolChEBI
Ethyl carbinolChEBI
EthylcarbinolChEBI
N-Propan-1-olChEBI
N-PropanolChEBI
N-Propyl alcoholChEBI
N-PropylalkoholChEBI
OptalChEBI
Osmosol extraChEBI
Propane-1-olChEBI
PropanolChEBI
Propanol-1ChEBI
UN 1274ChEBI
Propan-1-olKegg
1-Propyl alcoholHMDB
HydroxypropaneHMDB
PropanoleHMDB
PropanolenHMDB
Propylan-propyl alcoholHMDB
Propylic alcoholHMDB
1 PropanolHMDB
Alcohol, propylHMDB
N PropanolHMDB
Propyl alcoholChEBI
Chemical FormulaC3H8O
Average Mass60.0950 Da
Monoisotopic Mass60.05751 Da
IUPAC Namepropan-1-ol
Traditional Namepropanol
CAS Registry Number71-23-8
SMILES
CCCO
InChI Identifier
InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
InChI KeyBDERNNFJNOPAEC-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, 700 MHz, H2O, experimental)Ahselim2022-02-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 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 cepaFooDB
    • Heikki Kallio and Lea Salorinne. Comparison of Onion Varieties by Headspace Gas Chromatography-Ma...
Allium cepa L.FooDB
    • J. F. Carson and Francis F. Wong. The Volatile Flavor Components of Onions. J. Agric. Food Chem. ...
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. italicaFooDB
    • Charles F. Forney and Michael A. Jordan. Induction of Volatile Compounds in Broccoli by Postharve...
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carica papaya L.FooDB
CervidaeFooDB
Cervus canadensisFooDB
Coffea arabicaKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Pyrus communisFooDB
    • D. E. Heinz and W. C. Jennings. Volatile components of Bartlett Pear. V. Journal of Food Sci., 19...
Ribes nigrumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zea mays L.FooDB
Zingiber officinaleKNApSAcK Database
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).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-126.1 °CNot Available
Boiling Point296.00 to 298.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP0.25Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility391 g/LALOGPS
logP0.21ALOGPS
logP0.36ChemAxon
logS0.81ALOGPS
pKa (Strongest Acidic)16.85ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.53 m³·mol⁻¹ChemAxon
Polarizability7.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000820
DrugBank IDDB03175
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031044
KNApSAcK IDC00050488
Chemspider ID1004
KEGG Compound IDC05979
BioCyc IDPROPANOL
BiGG IDNot Available
Wikipedia LinkPropan-1-ol
METLIN ID5783
PubChem Compound1031
PDB IDNot Available
ChEBI ID28831
Good Scents IDrw1021881
References
General References
  1. Sich B, Kirch U, Tepel M, Zidek W, Schoner W: Pulse pressure correlates in humans with a proscillaridin A immunoreactive compound. Hypertension. 1996 May;27(5):1073-8. [PubMed:8621199 ]
  2. Glaros EN, Kim WS, Quinn CM, Wong J, Gelissen I, Jessup W, Garner B: Glycosphingolipid accumulation inhibits cholesterol efflux via the ABCA1/apolipoprotein A-I pathway: 1-phenyl-2-decanoylamino-3-morpholino-1-propanol is a novel cholesterol efflux accelerator. J Biol Chem. 2005 Jul 1;280(26):24515-23. Epub 2005 May 11. [PubMed:15890646 ]
  3. Lozier J, Takahashi N, Putnam FW: Purification of cyanogen bromide fragments from beta-2-glycoprotein I by high-performance liquid chromatography. J Chromatogr. 1983 Aug 26;266:545-54. [PubMed:6630361 ]
  4. Liebich HM, Al-Babbili O, Zlatkis A, Kim K: Gas-chromatographic and mass-spectrometric detection of low-molecular-weight aliphatic alcohols in urine of normal individuals and patients with diabetes mellitus. Clin Chem. 1975 Aug;21(9):1294-6. [PubMed:1149234 ]
  5. Flick JA, Schnaar RL, Perman JA: Thin-layer chromatographic determination of urinary excretion of lactulose, simplified and applied to cystic fibrosis patients. Clin Chem. 1987 Jul;33(7):1211-2. [PubMed:3594850 ]
  6. Moriya F, Hashimoto Y: Endogenous ethanol production in trauma victims associated with medical treatment. Nihon Hoigaku Zasshi. 1996 Aug;50(4):263-7. [PubMed:8810749 ]
  7. Kuba J, Knoll P, Husak V, Charamza O, Wiedermann M, Krc I: [On the use of Hg-197 labeled bromomercury hydroxypropane in splenic scintigraphy]. Z Gesamte Inn Med. 1965 Jul 15;20(14):431-6. [PubMed:5891990 ]
  8. Schwartz KD, Knoll P, Hamann D, Loechel M, Potschwadek B: [Scintigraphy of the spleen with bromomercuric hydroxypropane (197Hg-BMHP)]. Fortschr Geb Rontgenstr Nuklearmed. 1965 Sep;103(3):367-76. [PubMed:5893996 ]
  9. Li R, Manela J, Kong Y, Ladisch S: Cellular gangliosides promote growth factor-induced proliferation of fibroblasts. J Biol Chem. 2000 Nov 3;275(44):34213-23. [PubMed:10859325 ]
  10. Paravidino GF, Pagliaini R: [Splenic scintigraphy using erythrocytes devitalized by mercury hydroxypropane and labelled with Hg 197 or Cr 51]. Arch Maragliano Patol Clin. 1969 Nov-Dec;25(6):459-66. [PubMed:5409093 ]
  11. Rej R: Effect of incubation with Mg2+ on the measurement of alkaline phosphatase activity. Clin Chem. 1977 Oct;23(10):1903-11. [PubMed:902417 ]
  12. van Ketel WG: Allergy to benzylamine and benzyl-1-amino-3 chloro-2 hydroxypropane. Contact Dermatitis. 1984 Sep;11(3):186. [PubMed:6238790 ]
  13. Dodde WI, Maring JG, Hendriks G, Wachters FM, Groen HJ, de Vries EG, Uges DR: Determination of epirubicin and its metabolite epirubicinol in saliva and plasma by HPLC. Ther Drug Monit. 2003 Aug;25(4):433-40. [PubMed:12883225 ]
  14. Durley RC, Grapperhaus ML, Hickory BS, Massa MA, Wang JL, Spangler DP, Mischke DA, Parnas BL, Fobian YM, Rath NP, Honda DD, Zeng M, Connolly DT, Heuvelman DM, Witherbee BJ, Melton MA, Glenn KC, Krul ES, Smith ME, Sikorski JA: Chiral N,N-disubstituted trifluoro-3-amino-2-propanols are potent inhibitors of cholesteryl ester transfer protein. J Med Chem. 2002 Aug 29;45(18):3891-904. [PubMed:12190312 ]
  15. Memon N, Bhanger MI, Khuhawer MY: Determination of preservatives in cosmetics and food samples by micellar liquid chromatography. J Sep Sci. 2005 May;28(7):635-8. [PubMed:15912732 ]
  16. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
  17. Vujasinovic M, Kocar M, Kramer K, Bunc M, Brvar M: Poisoning with 1-propanol and 2-propanol. Hum Exp Toxicol. 2007 Dec;26(12):975-8. doi: 10.1177/0960327107087794. [PubMed:18375643 ]
  18. Li M, Chen S, Li J, Ji Z: Propanol addition improves natamycin biosynthesis of Streptomyces natalensis. Appl Biochem Biotechnol. 2014 Apr;172(7):3424-32. doi: 10.1007/s12010-014-0766-9. Epub 2014 Feb 16. [PubMed:24532463 ]