NP-MRD: Showing NP-Card for 2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione (NP0219892)

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Record Information

Version

2.0

Created at

2022-09-05 21:02:03 UTC

Updated at

2022-09-05 21:02:03 UTC

NP-MRD ID

NP0219892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione

Description

2-Chloro-1,3,7-trihydroxy-9-methoxy-1-methyl-1H,4H,6H-benzo[c]chromene-4,6-dione belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. 2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione is found in Acrocalymma vagum. Based on a literature review very few articles have been published on 2-chloro-1,3,7-trihydroxy-9-methoxy-1-methyl-1H,4H,6H-benzo[c]chromene-4,6-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223022D          

 23 25  0  0  0  0            999 V2000
   -3.0789    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768    0.7019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.6039    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.2539    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)OC3=C(C2=C1)C(C)(O)C(Cl)=C(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClO7/c1-15(21)9-6-3-5(22-2)4-7(17)8(6)14(20)23-12(9)10(18)11(19)13(15)16/h3-4,17,19,21H,1-2H3

> <INCHI_KEY>
ATVFPTGTIZZMLF-UHFFFAOYSA-N

> <FORMULA>
C15H11ClO7

> <MOLECULAR_WEIGHT>
338.7

> <EXACT_MASS>
338.0193304

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.697492467824055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-chloro-1,3,7-trihydroxy-9-methoxy-1-methyl-1H,4H,6H-benzo[c]chromene-4,6-dione

> <JCHEM_LOGP>
1.6572122836666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.372347015049145

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.262224508792513

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8474113440204976

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
81.66979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.747   1.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.207   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.437  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.207  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.207  -4.207   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.897  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127  -4.207   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.897  -5.541   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.413  -4.207   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.183  -2.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.264   0.320   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.450   1.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.723  -0.206   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       3.493   1.127   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       3.493  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.033  -1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.723  -2.874   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.493  -4.207   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13    3                                                       
CONECT   15   12   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₁ClO₇

Average Mass

338.7000 Da

Monoisotopic Mass

338.01933 Da

IUPAC Name

2-chloro-1,3,7-trihydroxy-9-methoxy-1-methyl-1H,4H,6H-benzo[c]chromene-4,6-dione

Traditional Name

2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)OC3=C(C2=C1)C(C)(O)C(Cl)=C(O)C3=O

InChI Identifier

InChI=1S/C15H11ClO7/c1-15(21)9-6-3-5(22-2)4-7(17)8(6)14(20)23-12(9)10(18)11(19)13(15)16/h3-4,17,19,21H,1-2H3

InChI Key

ATVFPTGTIZZMLF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acrocalymma vagum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
2-benzopyran
Benzopyran
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Vinylogous halide
Tertiary alcohol
Lactone
Ketone
Halohydrin
Chlorohydrin
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
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
logP	1.66	ChemAxon
pKa (Strongest Acidic)	6.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.67 m³·mol⁻¹	ChemAxon
Polarizability	30.7 Å³	ChemAxon
Number of Rings	3	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

162816063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione (NP0219892)

MOL for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

3D MOL for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

3D SDF for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

3D-SDF for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

PDB for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

3D PDB for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

SMILES for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

INCHI for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

Structure for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)

3D Structure for NP0219892 (2-chloro-1,3,7-trihydroxy-9-methoxy-1-methylbenzo[c]chromene-4,6-dione)