NP-MRD: Showing NP-Card for 6-Hydroxy-7-methoxy-4-phenylcoumarin (NP0051466)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:23 UTC

Updated at

2022-04-27 22:49:23 UTC

NP-MRD ID

NP0051466

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxy-7-methoxy-4-phenylcoumarin

Description

6-Hydroxy-7-methoxy-4-phenylcoumarin is found in Anadenanthera colubrina, Dalbergia baronii, Dalbergia cearensis, Dalbergia cochinchinensis, Dalbergia cultrata , Dalbergia melanoxylon, Dalbergia miscolobium, Dalbergia nigra, Dalbergia nitidula , Dalbergia odorifera , Dalbergia sissoides , Dalbergia sissoo , Dalbergia spruceana, Dalbergia stevensonii, Dalbergia volubilis , Goniorrhachis marginata, Machaerium kuhlmannii, Machaerium pedicellatum, Machaerium scleroxylon, Piptadenia macrocarpa, Prosopis kuntzei , Pterocarpus santalinus and Senna alata.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.2176    0.5046   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101    0.1666   -0.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8092    0.1517   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    0.4827    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    0.4695    1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842    0.7919    2.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    0.8067    3.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    1.1234    4.2394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350    0.4782    2.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    0.1350    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149   -0.1781    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982   -1.1997    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069   -1.5240   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5058   -0.8550   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506    0.1524   -1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    0.4774   -1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.1270    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -0.2038   -0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -0.1867   -1.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.5264   -2.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1276    0.2083   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950    1.6019   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1814   -0.0796    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3735    0.7590    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    0.4885    2.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -1.7205    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8835   -2.3146    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -1.0989   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8744    0.6827   -2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837    1.2851   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565   -0.4818   -1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277   -0.5233   -3.0426 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 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 17 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 19  3  1  0
 16 11  1  0
  6  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 18 31  1  0
 20 32  1  0
  9 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END

 
  Mrv0541 02271201342D          
 
 20 22  0  0  0  0            999 V2000
   14.3512   -8.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0652   -8.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3546   -7.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6438   -8.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0619   -9.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7829   -8.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6438   -6.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0721   -6.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9263   -8.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3477   -9.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7760   -9.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7864   -7.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9263   -7.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2121   -8.6435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3443  -10.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7726  -10.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5039   -7.0022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2121   -6.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0550  -11.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4980   -7.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051466

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)C(=CC(=O)O2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O4/c1-19-15-9-14-12(7-13(15)17)11(8-16(18)20-14)10-5-3-2-4-6-10/h2-9,17H,1H3

> <INCHI_KEY>
AZELSOYQOIUPBZ-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.2641

> <EXACT_MASS>
268.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.4253398682319

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-7-methoxy-4-phenyl-2H-chromen-2-one

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
2.7553216056666665

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.764832702864771

> <JCHEM_PKA_STRONGEST_BASIC>
-4.900790589723797

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
83.54540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dalbergin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      26.789 -15.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.122 -16.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.795 -13.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.468 -16.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.116 -17.679   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.461 -15.372   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.468 -13.052   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      28.135 -13.058   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.129 -15.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.782 -18.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.448 -18.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.468 -13.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.129 -13.821   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.796 -16.135   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.776 -19.980   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.442 -19.993   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      30.807 -13.071   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.796 -13.052   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      28.103 -20.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.463 -13.814   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    3   12                                                       
CONECT    9    4   14   13                                                  
CONECT   10    5   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17    8                                                  
CONECT   13    7   18    9                                                  
CONECT   14    9                                                            
CONECT   15   10   19                                                       
CONECT   16   11   19                                                       
CONECT   17   12                                                            
CONECT   18   13   20                                                       
CONECT   19   15   16                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₄

Average Mass

268.2641 Da

Monoisotopic Mass

268.07356 Da

IUPAC Name

6-hydroxy-7-methoxy-4-phenyl-2H-chromen-2-one

Traditional Name

dalbergin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)C(=CC(=O)O2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12O4/c1-19-15-9-14-12(7-13(15)17)11(8-16(18)20-14)10-5-3-2-4-6-10/h2-9,17H,1H3

InChI Key

AZELSOYQOIUPBZ-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, 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
Anadenanthera colubrina	Plant	KNApSAcK
Dalbergia baronii	Plant	KNApSAcK
Dalbergia cearensis	Plant	KNApSAcK
Dalbergia cochinchinensis	Plant	KNApSAcK
Dalbergia cultrata	Plant	KNApSAcK
Dalbergia melanoxylon	LOTUS Database	35616633
Dalbergia miscolobium	Plant	KNApSAcK
Dalbergia nigra	LOTUS Database	35616633
Dalbergia nitidula	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia sissoides	Plant	KNApSAcK
Dalbergia sissoo	Plant	KNApSAcK
Dalbergia spruceana	Plant	KNApSAcK
Dalbergia stevensonii	Plant	KNApSAcK
Dalbergia volubilis	Plant	KNApSAcK
Goniorrhachis marginata	Plant	KNApSAcK
Machaerium kuhlmannii	Plant	KNApSAcK
Machaerium pedicellatum	Plant	KNApSAcK
Machaerium scleroxylon	Plant	KNApSAcK
Piptadenia macrocarpa	Plant	KNApSAcK
Prosopis kuntzei	Plant	KNApSAcK
Pterocarpus santalinus	LOTUS Database	35616633
Senna alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Neoflavones

Direct Parent

Neoflavones

Alternative Parents

Substituents

4-phenylcoumarin
Hydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

neoflavonoid (CHEBI:4308 )
Neoflavonoids (C10414 )
Neoflavonoids (LMPK12100003 )

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	3.77	ALOGPS
logP	2.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.55 m³·mol⁻¹	ChemAxon
Polarizability	27.43 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

FDB029982

KNApSAcK ID

C00002519

Chemspider ID

Not Available

KEGG Compound ID

C10414

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Hydroxy-7-methoxy-4-phenylcoumarin (NP0051466)

MOL for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

3D MOL for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

3D SDF for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

3D-SDF for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

PDB for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

3D PDB for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

SMILES for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

INCHI for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

Structure for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)

3D Structure for NP0051466 (6-Hydroxy-7-methoxy-4-phenylcoumarin)