NP-MRD: Showing NP-Card for 2',3-Dihydroxy-5-methoxybibenzyl (NP0051644)

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Record Information

Version

2.0

Created at

2022-04-27 22:56:06 UTC

Updated at

2022-04-27 22:56:06 UTC

NP-MRD ID

NP0051644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',3-Dihydroxy-5-methoxybibenzyl

Description

Batatasin IV belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Thus, batatasin IV is considered to be an aromatic polyketide lipid molecule. Batatasin IV is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Batatasin IV has been detected, but not quantified in, root vegetables. 2',3-Dihydroxy-5-methoxybibenzyl is found in Bauhinia purpurea, Dioscorea alata , Dioscorea batatas , Dioscorea batatus , Dioscorea cayenensis, Dioscorea japonica, Dioscorea opposita , Dioscorea oppositifolia, Dioscorea rotundata and Pseudomonas cichorii. This could make batatasin IV a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.2818    1.8567    0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059    1.8472    0.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478    0.6975    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652   -0.5791    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575   -1.6702    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3357   -2.9790    0.0901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -1.5270   -0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -0.2680   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4852   -0.0593   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -0.0048    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.2030    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012    1.4417    0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645    1.5663    0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3517    0.4943    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7421   -0.7239   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -0.8843    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -2.1138   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    0.8152   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8988    1.7194   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541    2.8782    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6234    1.1399    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7040   -0.7168    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -3.4975   -0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347   -2.3804   -0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    0.9683   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -0.8316   -1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -0.9597    1.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    0.8069    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    2.2748    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0452    2.5333    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4239    0.6282    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177   -1.5918   -0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2898   -2.9037   -0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    1.8198   -0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 18  2  0
 18  8  1  0
  8  9  1  0
  9 10  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
 16 17  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 34  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
  7 24  1  0
  6 23  1  0
  4 22  1  0
M  END


  Mrv0541 05061306362D          

 18 19  0  0  0  0            999 V2000
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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   -2.8875    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    0.0000    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
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
  7  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC2=CC=CC=C2O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-18-14-9-11(8-13(16)10-14)6-7-12-4-2-3-5-15(12)17/h2-5,8-10,16-17H,6-7H2,1H3

> <INCHI_KEY>
IUMFLNFLJUUODE-UHFFFAOYSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.650775204126763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(2-hydroxyphenyl)ethyl]-5-methoxyphenol

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.7448065989999995

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.35856680730857

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.498795038851561

> <JCHEM_PKA_STRONGEST_BASIC>
-4.836123398972027

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
70.8212

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
batatasin IV

> <JCHEM_VEBER_RULE>
0

$$$$

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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   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  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -3.080   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      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   15                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   11   13                                                       
CONECT    9   11   14                                                       
CONECT   10   13   14                                                       
CONECT   11    6    8    9                                                  
CONECT   12    4    7   15                                                  
CONECT   13    8   10   16                                                  
CONECT   14    9   10   18                                                  
CONECT   15    5   12   17                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18    1   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
3-[2-(2-Hydroxyphenyl)ethyl]-5-methoxyphenol	Kegg
1-(2-Hydroxyphenyl)-2-(3-hydroxy-5-methoxyphenyl)ethane	HMDB
2',3-Dihydroxy-5-methoxybibenzyl	HMDB
2,3'-Dihydroxy-5'-methoxybibenzyl	HMDB
3-[2-(2-Hydroxyphenyl)ethyl]-5-methoxyphenol, 9ci	HMDB

Chemical Formula

C₁₅H₁₆O₃

Average Mass

244.2857 Da

Monoisotopic Mass

244.10994 Da

IUPAC Name

3-[2-(2-hydroxyphenyl)ethyl]-5-methoxyphenol

Traditional Name

batatasin IV

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC2=CC=CC=C2O)=CC(O)=C1

InChI Identifier

InChI=1S/C15H16O3/c1-18-14-9-11(8-13(16)10-14)6-7-12-4-2-3-5-15(12)17/h2-5,8-10,16-17H,6-7H2,1H3

InChI Key

IUMFLNFLJUUODE-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
Bauhinia purpurea	LOTUS Database	35616633
Dioscorea alata	Plant	KNApSAcK
Dioscorea batatas	Plant	KNApSAcK
Dioscorea batatus	Plant	KNApSAcK
Dioscorea cayenensis	LOTUS Database	35616633
Dioscorea japonica	LOTUS Database	35616633
Dioscorea opposita	Plant	KNApSAcK
Dioscorea oppositifolia	LOTUS Database	35616633
Dioscorea rotundata	Plant	KNApSAcK
Pseudomonas cichorii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:2997 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10247 )
Bibenzyls (C10247 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090032 )

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	2.98	ALOGPS
logP	3.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.82 m³·mol⁻¹	ChemAxon
Polarizability	26.65 Å³	ChemAxon
Number of Rings	2	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

HMDB0032641

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

181271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',3-Dihydroxy-5-methoxybibenzyl (NP0051644)

MOL for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

3D MOL for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

3D SDF for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

3D-SDF for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

PDB for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

3D PDB for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

SMILES for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

INCHI for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

Structure for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)

3D Structure for NP0051644 (2',3-Dihydroxy-5-methoxybibenzyl)