Showing NP-Card for Acrylic acid (NP0047297)

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Record Information
Version2.0
Created at2022-03-17 20:37:50 UTC
Updated at2022-03-17 20:37:50 UTC
NP-MRD IDNP0047297
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcrylic acid
DescriptionAcrylic acid, also known as 2-propenoic acid or acrylate, belongs to the class of organic compounds known as acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H. Acrylic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acrylic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Acrylic acid has been detected, but not quantified in, pineapples. This could make acrylic acid a potential biomarker for the consumption of these foods. Acrylic acid is found in Gynerium sagittatum , Paraburkholderia phymatum and Polygonum minus. Acrylic acid was first documented in 2014 (PMID: 24650085). A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group (PMID: 24673501).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047297 (Acrylic acid)

  Mrv0541 02231216182D          

  5  4  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 O   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   -1.4289    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
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3D MOL for NP0047297 (Acrylic acid)

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3D SDF for NP0047297 (Acrylic acid)
  Mrv0541 02231216182D          

  5  4  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 O   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   -1.4289    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)

> <INCHI_KEY>
NIXOWILDQLNWCW-UHFFFAOYSA-N

> <FORMULA>
C3H4O2

> <MOLECULAR_WEIGHT>
72.0627

> <EXACT_MASS>
72.021129372

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
6.377670052918477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
prop-2-enoic acid

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.5329472926666666

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.715808200933474

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.2914

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047297 (Acrylic acid)
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PDB for NP0047297 (Acrylic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0047297 (Acrylic acid)
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SMILES for NP0047297 (Acrylic acid)
OC(=O)C=C
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INCHI for NP0047297 (Acrylic acid)
InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
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Synonyms
Chemical FormulaC3H4O2
Average Mass72.0627 Da
Monoisotopic Mass72.02113 Da
IUPAC Nameprop-2-enoic acid
Traditional Nameacrylic acid
CAS Registry Number79-10-7
SMILES
OC(=O)C=C
InChI Identifier
InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChI KeyNIXOWILDQLNWCW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ananas comosusFooDB
Gynerium sagittatumPlant
Paraburkholderia phymatum-
Polygonum minusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAcrylic acids and derivatives  
Direct ParentAcrylic acids  
Alternative Parents
Substituents
  • Acrylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.46ALOGPS
logP0.53ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.29 m³·mol⁻¹ChemAxon
Polarizability6.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031647  
DrugBank IDDB02579  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008302  
KNApSAcK IDNot Available
Chemspider ID6333  
KEGG Compound IDC19501  
BioCyc IDMY149879  
BiGG IDNot Available
Wikipedia LinkAcrylic_acid  
METLIN IDNot Available
PubChem Compound6581  
PDB IDNot Available
ChEBI ID18308  
Good Scents IDNot Available
References
General References
  1. Johnston BF, Marshall WG, Parsons S, Urquhart AJ, Oswald ID: Investigation of acrylic acid at high pressure using neutron diffraction. J Phys Chem B. 2014 Apr 10;118(14):4044-51. doi: 10.1021/jp502095n. Epub 2014 Apr 2. [PubMed:24650085  ] 
  2. Yu Y, Huang L, Wu W, Jiang H: Palladium-catalyzed oxidative annulation of acrylic acid and amide with alkynes: a practical route to synthesize alpha-pyrones and pyridones. Org Lett. 2014 Apr 18;16(8):2146-9. doi: 10.1021/ol500611d. Epub 2014 Mar 27. [PubMed:24673501  ]