NP-MRD: Showing NP-Card for methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate (NP0318591)

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Record Information

Version

2.0

Created at

2022-09-11 19:10:44 UTC

Updated at

2022-09-11 19:10:44 UTC

NP-MRD ID

NP0318591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate

Description

Cryptosporiopsinol 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-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate was first documented in 2017 (PMID: 28398744). Based on a literature review very few articles have been published on Cryptosporiopsinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -2.2142    3.0033   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183    1.8067    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892    0.6401   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -0.6010   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -1.7631   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -2.0755   -1.2655 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.8542   -0.2762 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4699   -3.6495   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175   -2.0828   -0.1630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4890   -1.8441   -1.7730 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -0.7360    0.4272 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3462   -0.8228    1.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505    0.2342   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5010    0.5091   -1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.8532    0.9127 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    1.8001    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418    2.6567    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0805    3.3792   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9643    3.7402    0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401    1.9059    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7747    0.6046   -0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127   -3.4368    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -3.6332   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -2.6045    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -1.0806    2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    2.0265    1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    2.7081    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    1.3164   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 13 11  1  0
 11 12  1  1
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4 11  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 12 25  1  0
  9 24  1  1
  7 22  1  1
  8 23  1  0
  3 21  1  0
  2 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv1652309112221102D          

 16 16  0  0  0  0            999 V2000
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    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
    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
  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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)C(Cl)C(O)C(Cl)=C1\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C10H12Cl2O4/c1-3-4-5-6(11)7(13)8(12)10(5,15)9(14)16-2/h3-4,7-8,13,15H,1-2H3/b4-3+

> <INCHI_KEY>
NOCLOSXSSSZXNK-ONEGZZNKSA-N

> <FORMULA>
C10H12Cl2O4

> <MOLECULAR_WEIGHT>
267.1

> <EXACT_MASS>
266.0112643

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.339431327909058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,5-dichloro-1,4-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate

> <JCHEM_LOGP>
0.8501672606666671

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.767109653722194

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.767071759099709

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8311643683766485

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
61.467400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,5-dichloro-1,4-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.379   1.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.915   0.620   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  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       2.735  -1.536   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -1.651   1.651   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.304   3.422   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.816   3.422   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.032   4.747   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.356   3.438   0.000  0.00  0.00           O+0
HETATM   16  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                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂Cl₂O₄

Average Mass

267.1000 Da

Monoisotopic Mass

266.01126 Da

IUPAC Name

methyl 3,5-dichloro-1,4-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate

Traditional Name

methyl 3,5-dichloro-1,4-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)C(Cl)C(O)C(Cl)=C1\C=C\C

InChI Identifier

InChI=1S/C10H12Cl2O4/c1-3-4-5-6(11)7(13)8(12)10(5,15)9(14)16-2/h3-4,7-8,13,15H,1-2H3/b4-3+

InChI Key

NOCLOSXSSSZXNK-ONEGZZNKSA-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

Not Available

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

Tertiary alcohol
Methyl ester
Carboxylic acid ester
Chlorohydrin
Halohydrin
Secondary alcohol
Vinyl chloride
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Vinyl halide
Haloalkene
Chloroalkene
Organic oxide
Carbonyl group
Organochloride
Organohalogen compound
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	0.85	ChemAxon
pKa (Strongest Acidic)	10.77	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.47 m³·mol⁻¹	ChemAxon
Polarizability	24.34 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

110416537

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155978925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McMullin DR, Green BD, Prince NC, Tanney JB, Miller JD: Natural Products of Picea Endophytes from the Acadian Forest. J Nat Prod. 2017 May 26;80(5):1475-1483. doi: 10.1021/acs.jnatprod.6b01157. Epub 2017 Apr 11. [PubMed:28398744 ]
LOTUS database [Link]

Showing NP-Card for methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate (NP0318591)

MOL for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

3D MOL for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

3D SDF for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

3D-SDF for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

PDB for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

3D PDB for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

SMILES for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

INCHI for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

Structure for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)

3D Structure for NP0318591 (methyl 3,5-dichloro-1,4-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclopent-2-ene-1-carboxylate)