NP-MRD: Showing NP-Card for 6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one (NP0314687)

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Record Information

Version

2.0

Created at

2022-09-11 12:55:06 UTC

Updated at

2022-09-11 12:55:06 UTC

NP-MRD ID

NP0314687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one

Description

(?)-5,7-Dimethoxy-6-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-2H-1-benzopyran-2-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one is found in Toddalia asiatica. Based on a literature review very few articles have been published on (?)-5,7-Dimethoxy-6-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-2H-1-benzopyran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    0.1516    3.4037    2.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283    2.5499    1.0520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6226    1.5810    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.4152    1.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7295    0.4702    1.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8508    0.3342    1.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7426   -0.5645    1.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8194   -0.7186    2.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5553   -1.4022    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3739   -1.2613   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4528   -0.3155   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -0.2019   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1103   -1.0276   -1.8594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -2.2859   -2.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    0.7502   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606    1.0259   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306    0.7469   -0.4404 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1827    1.1188   -1.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4307   -0.6691   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.6065   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7385   -0.6592    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543   -1.2015    1.0533 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    4.2938    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    2.8668    3.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554    3.8074    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.0635    2.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2497   -2.1536    0.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1715   -1.8871   -1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -2.9300   -2.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2103   -2.2856   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -2.7670   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    2.0484   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8684    0.3564   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891    1.3670    0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9826    1.2319   -0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -1.1730   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -2.6141   -1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -1.7962   -1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939   -0.5457    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    0.2222    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262   -1.5871    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  1
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 10 28  1  0
  9 27  1  0
  4 26  1  0
M  END


  Mrv1652309112214552D          

 22 23  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 Cl  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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  3 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314687

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@H](O)C(C)(C)Cl)C(OC)=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19ClO5/c1-16(2,17)13(18)7-10-11(20-3)8-12-9(15(10)21-4)5-6-14(19)22-12/h5-6,8,13,18H,7H2,1-4H3/t13-/m0/s1

> <INCHI_KEY>
JDYJPQNEOXWJQN-ZDUSSCGKSA-N

> <FORMULA>
C16H19ClO5

> <MOLECULAR_WEIGHT>
326.77

> <EXACT_MASS>
326.0921014

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92270725954969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxy-2H-chromen-2-one

> <JCHEM_LOGP>
2.410737128666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.732328302135826

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3532796006457897

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
84.11640000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.437  -1.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.897  -4.414   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      -4.001  -3.850   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉ClO₅

Average Mass

326.7700 Da

Monoisotopic Mass

326.09210 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@H](O)C(C)(C)Cl)C(OC)=C2C=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C16H19ClO5/c1-16(2,17)13(18)7-10-11(20-3)8-12-9(15(10)21-4)5-6-14(19)22-12/h5-6,8,13,18H,7H2,1-4H3/t13-/m0/s1

InChI Key

JDYJPQNEOXWJQN-ZDUSSCGKSA-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
Toddalia asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Phenol ether
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Secondary alcohol
Chlorohydrin
Lactone
Halohydrin
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organohalogen compound
Organic oxygen compound
Organochloride
Alcohol
Organooxygen compound
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

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

95502779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

101628133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one (NP0314687)

MOL for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

3D MOL for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

3D SDF for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

3D-SDF for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

PDB for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

3D PDB for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

SMILES for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

INCHI for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

Structure for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)

3D Structure for NP0314687 (6-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one)