NP-MRD: Showing NP-Card for 3,4'-Dihydroxybibenzyl (NP0051659)

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Record Information

Version

2.0

Created at

2022-04-27 22:56:36 UTC

Updated at

2022-04-27 22:56:36 UTC

NP-MRD ID

NP0051659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4'-Dihydroxybibenzyl

Description

Lunularin 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, lunularin is considered to be an aromatic polyketide lipid molecule. Lunularin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lunularin is a dihydrostilbenoid found in common celery. It has also been found in the roots of Hydrangea macrophylla. It converts lunularic acid into lunularin. 3,4'-Dihydroxybibenzyl is found in Blasia pusilla, Corsinia coriandrina, Dumortiera hirsuta, Frullania bonincola, Frullania dilatata, Frullania tamarisci, Hydrangea macrophylla , Marchantia berteroana, Marchantia paleacea var. diptera , Marchantia polymorpha, Morus laevigata and Ricciocarpos natans. A lunularic acid decarboxylase has been detected from the liverwort Conocephalum conicum.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -5.7267    1.3814    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4082    0.9235    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.1164   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6186   -0.3534   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548   -0.0232    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3666   -0.5464    0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    0.3912   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531   -0.1078   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.9065   -1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345   -1.3653   -1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.0371   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -0.2324    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9684    0.0961    1.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947    0.2357    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2399    0.7810    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395    1.2459    1.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4918    0.8523    0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -0.1423   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.9770   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0240   -0.5810    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -1.5482   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    1.3828    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.5092   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.1500   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -1.9985   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033   -1.4055   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    0.6777    2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    0.8622    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671    1.0382    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    1.8809    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  2  0
 16  2  1  0
 14  8  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1533004171501152D          

 16 17  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CCC2=CC=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O2/c15-13-8-6-11(7-9-13)4-5-12-2-1-3-14(16)10-12/h1-3,6-10,15-16H,4-5H2

> <INCHI_KEY>
ILEYXPCRQKRNIJ-UHFFFAOYSA-N

> <FORMULA>
C14H14O2

> <MOLECULAR_WEIGHT>
214.264

> <EXACT_MASS>
214.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.853032924249376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(3-hydroxyphenyl)ethyl]phenol

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.9024778646666665

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.504755915682557

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.881328640467686

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4426068395465

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
64.358

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lunularin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8                                                       
CONECT   15    5   16                                                       
CONECT   16   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
3,4'-Ethylenebisphenol	Kegg
3,4'-Dihydroxybibenzyl	MeSH

Chemical Formula

C₁₄H₁₄O₂

Average Mass

214.2640 Da

Monoisotopic Mass

214.09938 Da

IUPAC Name

4-[2-(3-hydroxyphenyl)ethyl]phenol

Traditional Name

lunularin

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CCC2=CC=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C14H14O2/c15-13-8-6-11(7-9-13)4-5-12-2-1-3-14(16)10-12/h1-3,6-10,15-16H,4-5H2

InChI Key

ILEYXPCRQKRNIJ-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
Blasia pusilla	LOTUS Database	35616633
Corsinia coriandrina	-	KNApSAcK
Dumortiera hirsuta	-	KNApSAcK
Frullania bonincola	Plant	KNApSAcK
Frullania dilatata	Plant	KNApSAcK
Frullania tamarisci	Plant	KNApSAcK
Hydrangea macrophylla	Plant	KNApSAcK
Marchantia berteroana	Plant	KNApSAcK
Marchantia paleacea var. diptera	Plant	KNApSAcK
Marchantia polymorpha	Plant	KNApSAcK
Morus laevigata	Plant	KNApSAcK
Ricciocarpos natans	Plant	KNApSAcK

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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:6568 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10269 )
Bibenzyls (C10269 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090039 )

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	3.05	ALOGPS
logP	3.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.36 m³·mol⁻¹	ChemAxon
Polarizability	23.85 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002889

Chemspider ID

Not Available

KEGG Compound ID

C10269

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lunularin

METLIN ID

Not Available

PubChem Compound

181511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4'-Dihydroxybibenzyl (NP0051659)

MOL for NP0051659 (3,4'-Dihydroxybibenzyl)

3D MOL for NP0051659 (3,4'-Dihydroxybibenzyl)

3D SDF for NP0051659 (3,4'-Dihydroxybibenzyl)

3D-SDF for NP0051659 (3,4'-Dihydroxybibenzyl)

PDB for NP0051659 (3,4'-Dihydroxybibenzyl)

3D PDB for NP0051659 (3,4'-Dihydroxybibenzyl)

SMILES for NP0051659 (3,4'-Dihydroxybibenzyl)

INCHI for NP0051659 (3,4'-Dihydroxybibenzyl)

Structure for NP0051659 (3,4'-Dihydroxybibenzyl)

3D Structure for NP0051659 (3,4'-Dihydroxybibenzyl)