Np mrd loader

Showing NP-Card for Propargyl alcohol (NP0002712)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2020-11-23 19:38:33 UTC
Updated at2024-09-17 15:45:32 UTC
NP-MRD IDNP0002712
Secondary Accession NumbersNone
Natural Product Identification
Common NamePropargyl alcohol
Provided ByBMRBBMRB logo
Description2-Propyn-1-ol, also known as prop-2-yne-1-ol or 3-propynol, belongs to the class of organic compounds known as acetylides. Acetylides are compounds arising by replacement of one or both hydrogen atoms of acetylene (ethyne) by a metal or other cationic group. E.G. NaC#CH monosodium acetylide. By extension, analogous compounds derived from terminal acetylenes, RC#CH. The class is limited here to derivatives of acetylene where the hydrogen atom is replaced with an element with similar or lower electronegativity that carbon. 2-Propyn-1-ol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Propargyl alcohol is found in Foeniculum vulgare . Propargyl alcohol was first documented in 2008 (PMID: 18974778). Based on a literature review a significant number of articles have been published on 2-Propyn-1-ol (PMID: 23043843) (PMID: 33710232) (PMID: 31635103) (PMID: 28956235) (PMID: 28191692).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002712 (Propargyl alcohol)


  Mrv1652310101713192D          

  4  3  0  0  0  0            999 V2000
    1.6500   -1.4289    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
  2  1  3  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
Download

3D MOL for NP0002712 (Propargyl alcohol)

NP0002712
     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    1.7749   -0.2713   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.2749   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645   -0.2783   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469    1.0327   -0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.2644   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.7027    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3158   -0.9085   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5761    1.6675   -0.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  3  6  1  0
  3  7  1  0
  4  8  1  0
M  END
Download

3D SDF for NP0002712 (Propargyl alcohol)


  Mrv1652310101713192D          

  4  3  0  0  0  0            999 V2000
    1.6500   -1.4289    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
  2  1  3  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0002712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC#C

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2

> <INCHI_KEY>
TVDSBUOJIPERQY-UHFFFAOYSA-N

> <FORMULA>
C3H4O

> <MOLECULAR_WEIGHT>
56.0633

> <EXACT_MASS>
56.02621475

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
5.7799188476728505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
prop-2-yn-1-ol

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.29049402266666663

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.649209094621881

> <JCHEM_PKA_STRONGEST_BASIC>
-3.389635942012389

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
15.841499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propargyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002712 (Propargyl alcohol)

NP0002712
     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    1.7749   -0.2713   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.2749   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645   -0.2783   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469    1.0327   -0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.2644   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.7027    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3158   -0.9085   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5761    1.6675   -0.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  3  6  1  0
  3  7  1  0
  4  8  1  0
M  END
Download

PDB for NP0002712 (Propargyl alcohol)

HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0       3.080  -2.667   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
Download

3D PDB for NP0002712 (Propargyl alcohol)

COMPND    NP0002712
HETATM    1  C1  UNL     1       1.775  -0.271  -0.595  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.582  -0.275  -0.357  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.865  -0.278  -0.084  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.347   1.033  -0.181  1.00  0.00           O  
HETATM    5  H1  UNL     1       2.819  -0.264  -0.791  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.072  -0.703   0.925  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.316  -0.909  -0.891  1.00  0.00           H  
HETATM    8  H4  UNL     1      -0.576   1.667  -0.328  1.00  0.00           H  
CONECT    1    2    2    2    5
CONECT    2    3
CONECT    3    4    6    7
CONECT    4    8
END
Download

SMILES for NP0002712 (Propargyl alcohol)

OCC#C
Download

INCHI for NP0002712 (Propargyl alcohol)

InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2
Download
View in JSmolView NMR Assignments
Synonyms
ValueSource
1-Hydroxy-2-propyneChEBI
1-Propyn-3-olChEBI
1-Propyn-3-yl alcoholChEBI
2-PropynolChEBI
2-Propynyl alcoholChEBI
3-Hydroxy-1-propyneChEBI
3-PropynolChEBI
Acetylene carbinolChEBI
AcetylenylcarbinolChEBI
EthynylcarbinolChEBI
EthynylmethanolChEBI
NA 1986ChEBI
Prop-2-in-1-olChEBI
Prop-2-yne-1-olChEBI
Propargyl alcoholChEBI
Propynyl alcoholChEBI
Prop-2-yn-1-olKegg
Propargyl alcohol, sodium saltMeSH
Propargyl alcohol, lithium saltMeSH
Chemical FormulaC3H4O
Average Mass56.0633 Da
Monoisotopic Mass56.02621 Da
IUPAC Nameprop-2-yn-1-ol
Traditional Namepropargyl alcohol
CAS Registry NumberNot Available
SMILES
OCC#C
InChI Identifier
InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2
InChI KeyTVDSBUOJIPERQY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anethum foeniculumPlant
Foeniculum vulgareKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acetylides. Acetylides are compounds arising by replacement of one or both hydrogen atoms of acetylene (ethyne) by a metal or other cationic group. E.G. NaC#CH monosodium acetylide. By extension, analogous compounds derived from terminal acetylenes, RC#CH. The class is limited here to derivatives of acetylene where the hydrogen atom is replaced with an element with similar or lower electronegativity that carbon.
KingdomOrganic compounds
Super ClassAcetylides
ClassNot Available
Sub ClassNot Available
Direct ParentAcetylides
Alternative Parents
Substituents
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point113.60 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility935500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.380The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP-0.7ALOGPS
logP-0.29ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)13.65ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.84 m³·mol⁻¹ChemAxon
Polarizability5.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0180697
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00052136
Chemspider ID21106466
KEGG Compound IDC05986
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropargyl_alcohol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28905
Good Scents IDrw1278841
References
General References
  1. Authors unspecified: Toxicology and carcinogenesis studies of propargyl alcohol (CAS No. 107-19-7) in F344/N rats and B6C3F1 mice (inhalation studies). Natl Toxicol Program Tech Rep Ser. 2008 Sep;(552):1-172. [PubMed:18974778 ]
  2. Pimenta RS, da Silva JF, Buyer JS, Janisiewicz WJ: Endophytic fungi from plums (Prunus domestica) and their antifungal activity against Monilinia fructicola. J Food Prot. 2012 Oct;75(10):1883-9. doi: 10.4315/0362-028X.JFP-12-156. [PubMed:23043843 ]
  3. Sorbelli D, Segato J, Del Zotto A, Belpassi L, Zuccaccia D, Belanzoni P: The mechanism of the gold(I)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4-endo-dig cyclization. Dalton Trans. 2021 Apr 21;50(15):5154-5160. doi: 10.1039/d1dt00080b. [PubMed:33710232 ]
  4. Chen Q, Wang Y, Hua R: Base-Promoted Chemodivergent Formation of 1,4-Benzoxazepin-5(4H)-ones and 1,3-Benzoxazin-4(4H)-ones Switched by Solvents. Molecules. 2019 Oct 19;24(20). pii: molecules24203773. doi: 10.3390/molecules24203773. [PubMed:31635103 ]
  5. Shimada K, Sugawara A, Korenaga T, Kawashima H: Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma. Lipids. 2017 Dec;52(12):1019-1032. doi: 10.1007/s11745-017-4303-9. Epub 2017 Sep 27. [PubMed:28956235 ]
  6. Shoji T, Nagai D, Tanaka M, Araki T, Ohta A, Sekiguchi R, Ito S, Mori S, Okujima T: Synthesis of 2-Aminofurans by Sequential [2+2] Cycloaddition-Nucleophilic Addition of 2-Propyn-1-ols with Tetracyanoethylene and Amine-Induced Transformation into 6-Aminopentafulvenes. Chemistry. 2017 Apr 11;23(21):5126-5136. doi: 10.1002/chem.201700121. Epub 2017 Mar 23. [PubMed:28191692 ]