NP-MRD: Showing NP-Card for (3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one (NP0314163)

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Record Information

Version

1.0

Created at

2022-09-11 12:07:29 UTC

Updated at

2022-09-11 12:07:30 UTC

NP-MRD ID

NP0314163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one

Description

CHEMBL501733 belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. Based on a literature review very few articles have been published on CHEMBL501733.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    2.0902    1.1384   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    0.3753    0.7300 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5012    1.1239    1.3508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    2.0133    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377    3.0654    1.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0573    1.8746   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752    0.8729   -0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826   -0.2288    0.1427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8532    0.0528    1.4704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -1.5843   -0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7343   -2.1456   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6216   -1.5447   -0.7018 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7247   -0.5364   -2.1417 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -1.0242    0.5597 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2872   -1.8061    0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501    1.6544   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8719    0.5989   -0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6578    2.0139    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3466    0.4298    1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9376    2.6332   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564    0.8547   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -0.1615    0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353    0.8792    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -2.2668   -0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700   -3.2282   -0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -2.4170   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4432   -1.3159    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -1.3211    0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  6 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  6
 14 27  1  1
 15 28  1  0
M  END


  Mrv1652309112214072D          

 15 15  0  0  1  0            999 V2000
    1.9690    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492    1.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8889   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314    1.1921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.6598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3488    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0314163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)\C=C/[C@H](O)\C=C\C(Cl)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13ClO4/c1-6-10(14)8(11)4-2-7(12)3-5-9(13)15-6/h2-8,10,12,14H,1H3/b4-2+,5-3-/t6-,7-,8?,10+/m1/s1

> <INCHI_KEY>
IIIFVUMJBALUGH-NMTNZHRMSA-N

> <FORMULA>
C10H13ClO4

> <MOLECULAR_WEIGHT>
232.66

> <EXACT_MASS>
232.0502366

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.04200064810762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,9S,10R)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydro-2H-oxecin-2-one

> <JCHEM_LOGP>
0.9439933166666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.487392210355473

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.086688263538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0316697030257345

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
56.9233

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,9S,10R)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one

> <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       3.676   3.971   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   2.807   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.171   1.352   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.684   1.061   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.692   2.225   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.188  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.180  -1.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.267   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.659  -2.431   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.163   0.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.651   0.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.147   1.934   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -1.365   2.225   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       1.155   3.098   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.651   4.553   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃ClO₄

Average Mass

232.6600 Da

Monoisotopic Mass

232.05024 Da

IUPAC Name

(5S,9S,10R)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydro-2H-oxecin-2-one

Traditional Name

(5S,9S,10R)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)\C=C/[C@H](O)\C=C\C(Cl)[C@H]1O

InChI Identifier

InChI=1S/C10H13ClO4/c1-6-10(14)8(11)4-2-7(12)3-5-9(13)15-6/h2-8,10,12,14H,1H3/b4-2+,5-3-/t6-,7-,8?,10+/m1/s1

InChI Key

IIIFVUMJBALUGH-NMTNZHRMSA-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 oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.94	ChemAxon
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-3	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	0	ChemAxon
Refractivity	56.92 m³·mol⁻¹	ChemAxon
Polarizability	22.04 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

24710022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25111598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one (NP0314163)

MOL for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

3D MOL for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

3D SDF for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

3D-SDF for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

PDB for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

3D PDB for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

SMILES for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

INCHI for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

Structure for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)

3D Structure for NP0314163 ((3z,5s,6e,9s,10r)-8-chloro-5,9-dihydroxy-10-methyl-5,8,9,10-tetrahydrooxecin-2-one)