NP-MRD: Showing NP-Card for 6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol (NP0288435)

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Record Information

Version

2.0

Created at

2022-09-09 18:08:07 UTC

Updated at

2022-09-09 18:08:07 UTC

NP-MRD ID

NP0288435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol

Description

6-[3-(4-Hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol is found in Dracaena cinnabari. 6-[3-(4-Hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516192D          

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  Mrv1533004241516192D          

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 22 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC=C1CCC(C1=CC=C(O)C=C1)C1=CC2=C(OC(CC2)C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H30O6/c1-36-30-17-25(34)13-6-21(30)7-14-26(19-2-9-23(32)10-3-19)27-16-22-8-15-29(37-31(22)18-28(27)35)20-4-11-24(33)12-5-20/h2-6,9-13,16-18,26,29,32-35H,7-8,14-15H2,1H3

> <INCHI_KEY>
CNVYKHIMCHCMKA-UHFFFAOYSA-N

> <FORMULA>
C31H30O6

> <MOLECULAR_WEIGHT>
498.575

> <EXACT_MASS>
498.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.46641343435593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
7.114093782666665

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.673154758949071

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.183964935507559

> <JCHEM_PKA_STRONGEST_BASIC>
-4.558340160157304

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
142.6842

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.002  -3.080   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  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   20   30                                                  
CONECT   30   29                                                            
CONECT   31   25   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₀O₆

Average Mass

498.5750 Da

Monoisotopic Mass

498.20424 Da

IUPAC Name

6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC=C1CCC(C1=CC=C(O)C=C1)C1=CC2=C(OC(CC2)C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C31H30O6/c1-36-30-17-25(34)13-6-21(30)7-14-26(19-2-9-23(32)10-3-19)27-16-22-8-15-29(37-31(22)18-28(27)35)20-4-11-24(33)12-5-20/h2-6,9-13,16-18,26,29,32-35H,7-8,14-15H2,1H3

InChI Key

CNVYKHIMCHCMKA-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
Dracaena cinnabari	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
Linear 1,3-diarylpropanoid
Cinnamylphenol
Methoxyphenol
Benzopyran
1-benzopyran
Chromane
Phenol ether
Methoxybenzene
Anisole
Phenoxy compound
Phenol
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	5.28	ALOGPS
logP	7.11	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.68 m³·mol⁻¹	ChemAxon
Polarizability	54.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

101687708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol (NP0288435)

MOL for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

3D MOL for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

3D SDF for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

3D-SDF for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

PDB for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

3D PDB for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

SMILES for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

INCHI for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

Structure for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)

3D Structure for NP0288435 (6-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol)