NP-MRD: Showing NP-Card for (-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol (NP0077258)

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Record Information

Version

2.0

Created at

2022-04-28 22:25:17 UTC

Updated at

2022-04-28 22:25:17 UTC

NP-MRD ID

NP0077258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol

Description

(1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. (-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol is found in Pimenta dioica . Based on a literature review very few articles have been published on (1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200252D          

 15 15  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
    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  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  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
    2.1434    1.2375    0.0000 O   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
    0.0000    2.4750    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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  0  0  0
  7 12  1  6  0  0  0
  2 13  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)[C@H](O)[C@@H](O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C10H13ClO4/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,10,12-14H,5H2,1H3/t8-,10-/m0/s1

> <INCHI_KEY>
YGHRQWKTVXMGDU-WPRPVWTQSA-N

> <FORMULA>
C10H13ClO4

> <MOLECULAR_WEIGHT>
232.66

> <EXACT_MASS>
232.0502366

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.464410998543208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.8385814333333336

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.118266769799824

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908614358950306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.493279571954484

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
56.294

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -5.335   0.000   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    2                                                            
CONECT   14    1   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

(1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol

Traditional Name

(1S,2R)-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)[C@H](O)[C@@H](O)CCl

InChI Identifier

InChI=1S/C10H13ClO4/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,10,12-14H,5H2,1H3/t8-,10-/m0/s1

InChI Key

YGHRQWKTVXMGDU-WPRPVWTQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pimenta dioica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Chlorohydrin
Halohydrin
Ether
Aromatic alcohol
Alcohol
Organohalogen compound
Organochloride
Organooxygen compound
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	0.36	ALOGPS
logP	0.84	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.29 m³·mol⁻¹	ChemAxon
Polarizability	22.46 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

9022507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10847213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol (NP0077258)

MOL for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

3D MOL for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

3D SDF for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

3D-SDF for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

PDB for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

3D PDB for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

SMILES for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

INCHI for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

Structure for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)

3D Structure for NP0077258 ((-)-threo-3-Chloro-1-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol)