Np mrd loader

Showing NP-Card for 4-hydroxycyclopent-2-en-1-one (NP0326860)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-12 08:52:17 UTC
Updated at2022-09-12 08:52:17 UTC
NP-MRD IDNP0326860
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxycyclopent-2-en-1-one
Description4-Hydroxy-2-cyclopentenone 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). 4-hydroxycyclopent-2-en-1-one is found in Passiflora tetrandra. 4-hydroxycyclopent-2-en-1-one was first documented in 2002 (PMID: 12400155). Based on a literature review very few articles have been published on 4-Hydroxy-2-cyclopentenone (PMID: 18416578).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0326860 (4-hydroxycyclopent-2-en-1-one)


  Mrv1652309122210522D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    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
    1.2352    0.6294    0.0000 C   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
   -0.3297   -0.8227    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
Download

3D MOL for NP0326860 (4-hydroxycyclopent-2-en-1-one)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -1.5628    1.9065    0.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    1.0248    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    1.2727   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.1261   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2692   -1.0156   -0.1654 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4759   -1.4480    1.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1196   -0.3963   -0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099    2.2554   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -0.0272   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907   -1.8211   -0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -0.6367    1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5242   -0.3954   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090   -0.8449    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  1  0
  7  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  6 11  1  0
  5 10  1  6
  7 12  1  0
  7 13  1  0
  3  8  1  0
  4  9  1  0
M  END
Download

3D SDF for NP0326860 (4-hydroxycyclopent-2-en-1-one)


  Mrv1652309122210522D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    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
    1.2352    0.6294    0.0000 C   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
   -0.3297   -0.8227    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O2/c6-4-1-2-5(7)3-4/h1-2,4,6H,3H2

> <INCHI_KEY>
DHNDDRBMUVFQIZ-UHFFFAOYSA-N

> <FORMULA>
C5H6O2

> <MOLECULAR_WEIGHT>
98.101

> <EXACT_MASS>
98.036779433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.391051574385054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxycyclopent-2-en-1-one

> <JCHEM_LOGP>
-0.033454517666666614

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.189731988963732

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.662630478331312

> <JCHEM_PKA_STRONGEST_BASIC>
-2.945288865994942

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.1012

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0326860 (4-hydroxycyclopent-2-en-1-one)

Download
PDB for NP0326860 (4-hydroxycyclopent-2-en-1-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

Download
3D PDB for NP0326860 (4-hydroxycyclopent-2-en-1-one)
Download
SMILES for NP0326860 (4-hydroxycyclopent-2-en-1-one)
OC1CC(=O)C=C1
Download
INCHI for NP0326860 (4-hydroxycyclopent-2-en-1-one)
InChI=1S/C5H6O2/c6-4-1-2-5(7)3-4/h1-2,4,6H,3H2
Download
View in JSmol
Synonyms
ValueSource
4-Hydroxy-2-cyclopentenone, (R)-isomerMeSH
Chemical FormulaC5H6O2
Average Mass98.1010 Da
Monoisotopic Mass98.03678 Da
IUPAC Name4-hydroxycyclopent-2-en-1-one
Traditional Name4-hydroxycyclopent-2-en-1-one
CAS Registry NumberNot Available
SMILES
OC1CC(=O)C=C1
InChI Identifier
InChI=1S/C5H6O2/c6-4-1-2-5(7)3-4/h1-2,4,6H,3H2
InChI KeyDHNDDRBMUVFQIZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tetrapathaea tetrandraLOTUS 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
  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • 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-0.033ChemAxon
pKa (Strongest Acidic)14.66ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.1 m³·mol⁻¹ChemAxon
Polarizability9.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3380656  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4169160  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yamada Y: [Studies on discovery and synthesis of bioactive marine organic molecules]. Yakugaku Zasshi. 2002 Oct;122(10):727-43. doi: 10.1248/yakushi.122.727. [PubMed:12400155  ] 
  2. Pandya BA, Snapper ML: A cross-metathesis route to the 5-F(2)-isoprostanes. J Org Chem. 2008 May 16;73(10):3754-8. doi: 10.1021/jo702702s. Epub 2008 Apr 17. [PubMed:18416578  ] 
  3. LOTUS database [Link]