NP-MRD: Showing NP-Card for 5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol (NP0323619)

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Record Information

Version

2.0

Created at

2022-09-12 03:09:50 UTC

Updated at

2022-09-12 03:09:50 UTC

NP-MRD ID

NP0323619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol

Description

7-Hydroxy-5-methoxyflavan, also known as (2S)-5-methoxy flavan-7-ol, belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. 5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol is found in Calamus draco. 7-Hydroxy-5-methoxyflavan is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.9255    1.4771   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520    1.4169   -0.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8623    0.1994   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040   -1.0200   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405   -2.2197    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -3.4026   -0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789   -2.1611    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7845   -0.9670    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    0.1898    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162    1.4965    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.4210   -0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795    0.2898    0.7974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7029    0.1629    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -0.9752    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7497   -1.1309    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3977   -0.1522   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6975    0.9864   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615    1.1318   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9111    0.5561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    0.6709   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5519    1.4187    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1943    2.4298   -0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602   -1.0425   -0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681   -4.2960    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -3.1082    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    2.1312   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0277    1.9932    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066    2.3761    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404    1.2183   -1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389    0.5827    1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948   -1.7388    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2963   -2.0254    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379   -0.2508   -0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.7863   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    2.0225   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 19  1  0
 19  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4  3  1  0
 18 13  1  0
  8  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  1
  7 25  1  0
  6 24  1  0
  4 23  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv0541 05061309572D          

 19 21  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.7145    1.2375    0.0000 C   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    2.4750    0.0000 C   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
    3.5724    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18 15  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-18-15-9-12(17)10-16-13(15)7-8-14(19-16)11-5-3-2-4-6-11/h2-6,9-10,14,17H,7-8H2,1H3

> <INCHI_KEY>
UNCVBXFEZHBZKN-UHFFFAOYSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.2964

> <EXACT_MASS>
256.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.216782746524945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.623035321666666

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.854652759614286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.571336160108634

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
73.15870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+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   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   12   15                                                       
CONECT   10   12   16                                                       
CONECT   11    5    6   14                                                  
CONECT   12    9   10   17                                                  
CONECT   13    7   15   16                                                  
CONECT   14    8   11   19                                                  
CONECT   15    9   13   18                                                  
CONECT   16   10   13   19                                                  
CONECT   17   12                                                            
CONECT   18    1   15                                                       
CONECT   19   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
(2S)-5-Methoxy flavan-7-ol	HMDB
3,4-Dihydro-5-methoxy-2-phenyl-2H-1-benzopyran-7-ol	HMDB

Chemical Formula

C₁₆H₁₆O₃

Average Mass

256.2964 Da

Monoisotopic Mass

256.10994 Da

IUPAC Name

5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

5-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

Not Available

SMILES

COC1=C2CCC(OC2=CC(O)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H16O3/c1-18-15-9-12(17)10-16-13(15)7-8-14(19-16)11-5-3-2-4-6-11/h2-6,9-10,14,17H,7-8H2,1H3

InChI Key

UNCVBXFEZHBZKN-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
Calamus draco	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	3.47	ALOGPS
logP	3.62	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.16 m³·mol⁻¹	ChemAxon
Polarizability	28.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037686

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016813

KNApSAcK ID

C00008750

Chemspider ID

303396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

342294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol (NP0323619)

MOL for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

3D MOL for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

3D SDF for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

3D-SDF for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

PDB for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

3D PDB for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

SMILES for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

INCHI for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

Structure for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)

3D Structure for NP0323619 (5-methoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-7-ol)