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Showing NP-Card for 3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one (NP0319981)

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Record Information
Version2.0
Created at2022-09-11 21:17:59 UTC
Updated at2022-09-11 21:17:59 UTC
NP-MRD IDNP0319981
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one
Description3-Amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. 3-Amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)


  Mrv1533004241510392D          

 10 10  0  0  0  0            999 V2000
    1.4652   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)

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3D SDF for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)

  Mrv1533004241510392D          

 10 10  0  0  0  0            999 V2000
    1.4652   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC(=O)C(O)(C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C7H9NO2/c1-2-7(10)4-5(8)3-6(7)9/h2-3,10H,1,4,8H2

> <INCHI_KEY>
RNZVUWAMBDXWDJ-UHFFFAOYSA-N

> <FORMULA>
C7H9NO2

> <MOLECULAR_WEIGHT>
139.154

> <EXACT_MASS>
139.063328534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.850132360749692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-0.5591383526666669

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.896723314821802

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.55548572608614

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7757577409113847

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
39.019499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)
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PDB for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       2.735  -1.536   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    2                                                       
CONECT    9    6   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)
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SMILES for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)
NC1=CC(=O)C(O)(C1)C=C
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INCHI for NP0319981 (3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one)
InChI=1S/C7H9NO2/c1-2-7(10)4-5(8)3-6(7)9/h2-3,10H,1,4,8H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H9NO2
Average Mass139.1540 Da
Monoisotopic Mass139.06333 Da
IUPAC Name3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one
Traditional Name3-amino-5-ethenyl-5-hydroxycyclopent-2-en-1-one
CAS Registry NumberNot Available
SMILES
NC1=CC(=O)C(O)(C1)C=C
InChI Identifier
InChI=1S/C7H9NO2/c1-2-7(10)4-5(8)3-6(7)9/h2-3,10H,1,4,8H2
InChI KeyRNZVUWAMBDXWDJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAcyloins  
Alternative Parents
Substituents
  • Acyloin
    • 

  • Tertiary alcohol
    • 

  • Vinylogous amide
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Enamine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP-0.92ALOGPS
logP-0.56ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)12.56ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.02 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72789534  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]