NP-MRD: Showing NP-Card for methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate (NP0326271)

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Record Information

Version

2.0

Created at

2022-09-12 07:41:02 UTC

Updated at

2022-09-12 07:41:02 UTC

NP-MRD ID

NP0326271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate

Description

Methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate is found in Lachnum palmae. Based on a literature review very few articles have been published on methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122209412D          

 17 17  0  0  0  0            999 V2000
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 Cl  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
    1.4652   -0.8227    0.0000 Cl  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
   -0.8843    0.8843    0.0000 Cl  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
    0.1628    1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9728    1.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528    2.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977    1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    2.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)C(Cl)C(=O)C(Cl)=C1C(Cl)=CC

> <INCHI_IDENTIFIER>
InChI=1S/C10H9Cl3O4/c1-3-4(11)5-6(12)7(14)8(13)10(5,16)9(15)17-2/h3,8,16H,1-2H3

> <INCHI_KEY>
PSKFUYJUFHLCDN-UHFFFAOYSA-N

> <FORMULA>
C10H9Cl3O4

> <MOLECULAR_WEIGHT>
299.53

> <EXACT_MASS>
297.9566419

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
25.40225793112468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate

> <JCHEM_LOGP>
1.8542957516666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.585372429224934

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.577948292890325

> <JCHEM_PKA_STRONGEST_BASIC>
-4.736338459687894

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
65.492

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       4.915   0.620   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.735  -1.536   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -1.651   1.651   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.304   3.422   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.816   3.422   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.032   4.747   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.356   3.438   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.112   4.779   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylic acid	Generator

Chemical Formula

C₁₀H₉Cl₃O₄

Average Mass

299.5300 Da

Monoisotopic Mass

297.95664 Da

IUPAC Name

methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate

Traditional Name

methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)C(Cl)C(=O)C(Cl)=C1C(Cl)=CC

InChI Identifier

InChI=1S/C10H9Cl3O4/c1-3-4(11)5-6(12)7(14)8(13)10(5,16)9(15)17-2/h3,8,16H,1-2H3

InChI Key

PSKFUYJUFHLCDN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lachnum palmae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Alpha-haloketone
Alpha-chloroketone
Tertiary alcohol
Methyl ester
Carboxylic acid ester
Chlorohydrin
Halohydrin
Ketone
Cyclic ketone
Vinyl chloride
Monocarboxylic acid or derivatives
Vinyl halide
Carboxylic acid derivative
Haloalkene
Chloroalkene
Organic oxide
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.85	ChemAxon
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.49 m³·mol⁻¹	ChemAxon
Polarizability	25.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76416518

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate (NP0326271)

MOL for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

3D MOL for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

3D SDF for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

3D-SDF for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

PDB for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

3D PDB for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

SMILES for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

INCHI for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

Structure for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)

3D Structure for NP0326271 (methyl 3,5-dichloro-2-(1-chloroprop-1-en-1-yl)-1-hydroxy-4-oxocyclopent-2-ene-1-carboxylate)