Np mrd loader

Showing NP-Card for (+)-Chlorosphaeropsidone (NP0074393)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-28 19:33:31 UTC
Updated at2022-04-28 19:33:31 UTC
NP-MRD IDNP0074393
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Chlorosphaeropsidone
Description(4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (+)-Chlorosphaeropsidone is found in Sphaeropsis sapinea f.sp.cupressi. Based on a literature review very few articles have been published on (4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074393 ((+)-Chlorosphaeropsidone)


  Mrv1652304282221332D          

 12 12  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  6  0  0  0
  1 12  1  1  0  0  0
M  END
Download

3D MOL for NP0074393 ((+)-Chlorosphaeropsidone)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.1433   -0.1021   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -0.5054    0.7902 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -0.5283    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790   -1.6646    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -1.6131   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7547   -2.6555   -0.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -0.3859   -0.3283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5139   -0.6355    0.7437 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3345    0.8156    0.1653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8352    1.9411   -0.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285    0.7300   -0.1357 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3601    0.8672   -1.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823    0.9600   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -0.0641    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1896   -0.7783   -0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529   -2.6034    0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951   -0.2362   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    0.9251    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    2.7703   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.6014    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778    1.1618   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  6
  9 18  1  1
 10 19  1  0
 11 20  1  1
 12 21  1  0
M  END
Download

3D SDF for NP0074393 ((+)-Chlorosphaeropsidone)


  Mrv1652304282221332D          

 12 12  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  6  0  0  0
  1 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074393

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)[C@@H](Cl)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H9ClO4/c1-12-4-2-3(9)5(8)7(11)6(4)10/h2,5-7,10-11H,1H3/t5-,6-,7+/m1/s1

> <INCHI_KEY>
QSEIAQVQXUHJCV-QYNIQEEDSA-N

> <FORMULA>
C7H9ClO4

> <MOLECULAR_WEIGHT>
192.6

> <EXACT_MASS>
192.0189365

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.797608242300832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.5823755740000003

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.720450453718815

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.053721005535143

> <JCHEM_PKA_STRONGEST_BASIC>
-3.73873570353926

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
43.0964

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0074393 ((+)-Chlorosphaeropsidone)

Download
PDB for NP0074393 ((+)-Chlorosphaeropsidone)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9                                                            
CONECT   11    2                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0074393 ((+)-Chlorosphaeropsidone)
Download
SMILES for NP0074393 ((+)-Chlorosphaeropsidone)
COC1=CC(=O)[C@@H](Cl)[C@H](O)[C@@H]1O
Download
INCHI for NP0074393 ((+)-Chlorosphaeropsidone)
InChI=1S/C7H9ClO4/c1-12-4-2-3(9)5(8)7(11)6(4)10/h2,5-7,10-11H,1H3/t5-,6-,7+/m1/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC7H9ClO4
Average Mass192.6000 Da
Monoisotopic Mass192.01894 Da
IUPAC Name(4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one
Traditional Name(4S,5R,6S)-6-chloro-4,5-dihydroxy-3-methoxycyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)[C@@H](Cl)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C7H9ClO4/c1-12-4-2-3(9)5(8)7(11)6(4)10/h2,5-7,10-11H,1H3/t5-,6-,7+/m1/s1
InChI KeyQSEIAQVQXUHJCV-QYNIQEEDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 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 NMR1H NMR Spectrum (1D, 1000 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 NMR1H NMR Spectrum (1D, 200 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 NMR1H NMR Spectrum (1D, 300 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 NMR1H NMR Spectrum (1D, 400 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 NMR1H NMR Spectrum (1D, 500 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 NMR1H NMR Spectrum (1D, 600 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 NMR1H NMR Spectrum (1D, 700 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 NMR1H NMR Spectrum (1D, 800 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
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sphaeropsis sapinea f.sp.cupressiFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Alpha-haloketone
    • 

  • Alpha-chloroketone
    • 

  • Vinylogous ester
    • 

  • 1,2-diol
    • 

  • Chlorohydrin
    • 

  • Secondary alcohol
    • 

  • Halohydrin
    • 

  • Organic oxide
    • 

  • Organohalogen compound
    • 

  • Organochloride
    • 

  • Hydrocarbon derivative
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • 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-0.45ALOGPS
logP-0.58ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.1 m³·mol⁻¹ChemAxon
Polarizability16.8 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 ID61693975  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound130894917  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References