NP-MRD: Showing NP-Card for 2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one (NP0324788)

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Record Information

Version

2.0

Created at

2022-09-12 05:04:31 UTC

Updated at

2022-09-12 05:04:31 UTC

NP-MRD ID

NP0324788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one

Description

Palmariol B 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). Palmariol B is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one is found in Lachnum palmae. 2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one was first documented in 2012 (PMID: 23011274). A benzochromenone that is 6H-benzochromen-6-one which is substituted by a methyl group at position 1, chloro group at position 2, hydroxy groups at positions positions 3 and 7, and by a methoxy group at position 9.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.5754    1.7838   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7101    0.4890    0.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.3043    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.5676    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5845   -2.3780    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -3.6397    1.6151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -1.8699    0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896   -2.6124    0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -3.7939    1.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -2.1275    0.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -0.9328    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4089   -0.5024   -0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    0.7416   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8883    1.2017   -0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    1.5612   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492    3.1792   -1.4917 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    1.1582   -0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.0532   -0.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -0.0943   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492   -0.5755    0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413    0.2177    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    2.1445   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439    2.5110    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    1.8075   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -1.9978    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -4.3741    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -1.1679    0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.6047   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522    1.6917   -1.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    2.8122   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361    2.7974   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    1.1835   -0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 19 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 12 27  1  0
 14 28  1  0
 18 29  1  0
 18 30  1  0
 18 31  1  0
 21 32  1  0
M  END


  Mrv1533004231520032D          

 21 23  0  0  0  0            999 V2000
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   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
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)OC3=CC(O)=C(Cl)C(C)=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClO5/c1-6-12-8-3-7(20-2)4-9(17)13(8)15(19)21-11(12)5-10(18)14(6)16/h3-5,17-18H,1-2H3

> <INCHI_KEY>
WMOJBLDBGQOTOS-UHFFFAOYSA-N

> <FORMULA>
C15H11ClO5

> <MOLECULAR_WEIGHT>
306.7

> <EXACT_MASS>
306.0295012

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.361397303203518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-chloro-3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.927991598

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.458501234357731

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.182723297266381

> <JCHEM_PKA_STRONGEST_BASIC>
-4.076719060261511

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.2101

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.415   1.127   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      11.495  -4.207   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-Chloro-3,7-dihydroxy-9-methoxy-1-methyl-6H-dibenzo[b,D]pyran-6-one	ChEBI

Chemical Formula

C₁₅H₁₁ClO₅

Average Mass

306.7000 Da

Monoisotopic Mass

306.02950 Da

IUPAC Name

2-chloro-3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one

Traditional Name

2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)OC3=CC(O)=C(Cl)C(C)=C3C2=C1

InChI Identifier

InChI=1S/C15H11ClO5/c1-6-12-8-3-7(20-2)4-9(17)13(8)15(19)21-11(12)5-10(18)14(6)16/h3-5,17-18H,1-2H3

InChI Key

WMOJBLDBGQOTOS-UHFFFAOYSA-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
Lachnum palmae	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

Isocoumarin
Coumarin
Benzopyran
2-benzopyran
1-benzopyran
Anisole
2-halophenol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Aryl chloride
Aryl halide
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
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	2.82	ALOGPS
logP	3.93	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.18	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.21 m³·mol⁻¹	ChemAxon
Polarizability	29.36 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

Not Available

PDB ID

Not Available

ChEBI ID

141334

Good Scents ID

Not Available

References

General References

Meng X, Mao Z, Lou J, Xu L, Zhong L, Peng Y, Zhou L, Wang M: Benzopyranones from the endophytic fungus Hyalodendriella sp. Ponipodef12 and their bioactivities. Molecules. 2012 Sep 25;17(10):11303-14. doi: 10.3390/molecules171011303. [PubMed:23011274 ]
LOTUS database [Link]

Showing NP-Card for 2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one (NP0324788)

MOL for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

3D MOL for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

3D SDF for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

3D-SDF for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

PDB for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

3D PDB for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

SMILES for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

INCHI for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

Structure for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)

3D Structure for NP0324788 (2-chloro-3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one)