NP-MRD: Showing NP-Card for 4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol (NP0211702)

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Record Information

Version

2.0

Created at

2022-09-05 10:05:44 UTC

Updated at

2022-09-05 10:05:44 UTC

NP-MRD ID

NP0211702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol

Description

4'-[4-(Hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. 4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol is found in Dendrobium nobile. 4'-[4-(Hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501162D          

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M  END

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  Mrv1533004181501162D          

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M  END
> <DATABASE_ID>
NP0211702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC(CCC2=CC(O)=C(C(OC)=C2)C2=C(OC)C=C(C=C2OC)C2OOC2CO)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O8/c1-30-19-7-5-6-16(10-19)8-9-17-11-20(29)25(21(12-17)31-2)26-22(32-3)13-18(14-23(26)33-4)27-24(15-28)34-35-27/h5-7,10-14,24,27-29H,8-9,15H2,1-4H3

> <INCHI_KEY>
HVCTXCDEFSHFMW-UHFFFAOYSA-N

> <FORMULA>
C27H30O8

> <MOLECULAR_WEIGHT>
482.529

> <EXACT_MASS>
482.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
52.0249309971739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2,6-dimethoxyphenyl}-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.540437002999999

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.468382750988503

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.025185505432196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0313300693670477

> <JCHEM_POLAR_SURFACE_AREA>
95.84000000000002

> <JCHEM_REFRACTIVITY>
129.6782

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{4-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2,6-dimethoxyphenyl}-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  23.738   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  22.198   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  21.428   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  22.198   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  21.428   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  19.888   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  19.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  17.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  16.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  15.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  14.498   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  12.958   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  12.188   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  12.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  12.958   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  12.188   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667  12.958   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000  14.498   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  10.648   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   9.878   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  10.648   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335   9.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   8.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   7.568   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   8.338   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000   9.878   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  10.648   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667   9.878   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   6.028   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.245   4.939   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.423   4.939   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.963   4.939   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.733   3.605   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  19.888   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   10                                                       
CONECT   19   14   20   26                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   29   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₈

Average Mass

482.5290 Da

Monoisotopic Mass

482.19407 Da

IUPAC Name

2-{4-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2,6-dimethoxyphenyl}-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

Traditional Name

2-{4-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2,6-dimethoxyphenyl}-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

CAS Registry Number

Not Available

SMILES

COC1=CC=CC(CCC2=CC(O)=C(C(OC)=C2)C2=C(OC)C=C(C=C2OC)C2OOC2CO)=C1

InChI Identifier

InChI=1S/C27H30O8/c1-30-19-7-5-6-16(10-19)8-9-17-11-20(29)25(21(12-17)31-2)26-22(32-3)13-18(14-23(26)33-4)27-24(15-28)34-35-27/h5-7,10-14,24,27-29H,8-9,15H2,1-4H3

InChI Key

HVCTXCDEFSHFMW-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
Dendrobium nobile	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Stilbene
Biphenyl
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Dialkyl peroxide
1,2-dioxetane
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.79	ALOGPS
logP	4.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.68 m³·mol⁻¹	ChemAxon
Polarizability	52.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

101443793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol (NP0211702)

MOL for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

3D MOL for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

3D SDF for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

3D-SDF for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

PDB for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

3D PDB for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

SMILES for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

INCHI for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

Structure for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)

3D Structure for NP0211702 (4'-[4-(hydroxymethyl)-1,2-dioxetan-3-yl]-2',6,6'-trimethoxy-4-[2-(3-methoxyphenyl)ethyl]-[1,1'-biphenyl]-2-ol)