NP-MRD: Showing NP-Card for 4,4'-dihydroxybibenzyl (NP0267388)

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Record Information

Version

2.0

Created at

2022-09-08 12:09:30 UTC

Updated at

2022-09-08 12:09:30 UTC

NP-MRD ID

NP0267388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-dihydroxybibenzyl

Description

4,4'-Dihydroxybibenzyl 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, 4,4'-dihydroxybibenzyl is considered to be an aromatic polyketide lipid molecule. 4,4'-dihydroxybibenzyl is found in Gastrodia elata. 4,4'-Dihydroxybibenzyl is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    5.9012    0.4095   -0.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418    0.1101   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9916    0.0309    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423   -0.2670    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8156   -0.4916   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -0.8073   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    0.5067   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.2782    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6875    0.0924   -0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456   -0.1206   -0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5580   -0.1479    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9095   -0.3592    0.7784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7383    0.0336    1.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.2446    1.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3610   -0.4136   -1.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121   -0.1151   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445   -0.3886   -0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973    0.1985    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206   -0.3266    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -1.3525    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0197   -1.4417   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    1.1039    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854    0.9923   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756    0.1165   -1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084   -0.2661   -1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3268   -1.2848    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1070    0.0180    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    0.3854    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -0.5917   -2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195   -0.0589   -2.6487 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
 11 13  1  0
 13 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
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1533004171507272D          

 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
    2.1434   -8.6625    0.0000 O   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
    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
 11 13  1  0  0  0  0
 13 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>
NP0267388

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h3-10,15-16H,1-2H2

> <INCHI_KEY>
URFNSYWAGGETFK-UHFFFAOYSA-N

> <FORMULA>
C14H14O2

> <MOLECULAR_WEIGHT>
214.264

> <EXACT_MASS>
214.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.913122235610757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.9024778646666665

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.590288724066161

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.988042495362745

> <JCHEM_PKA_STRONGEST_BASIC>
-5.442599854757465

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
64.358

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4'-dihydroxybibenzyl

> <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  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    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
4,4'-(1,2-Ethanediyl)bisphenol	Kegg

Chemical Formula

C₁₄H₁₄O₂

Average Mass

214.2640 Da

Monoisotopic Mass

214.09938 Da

IUPAC Name

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

Traditional Name

4,4'-dihydroxybibenzyl

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H14O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h3-10,15-16H,1-2H2

InChI Key

URFNSYWAGGETFK-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
Gastrodia elata	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
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:34366 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C14341 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090042 )

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	3.07	ALOGPS
logP	3.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.99	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	23.91 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14341

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

80152

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'-dihydroxybibenzyl (NP0267388)

MOL for NP0267388 (4,4'-dihydroxybibenzyl)

3D MOL for NP0267388 (4,4'-dihydroxybibenzyl)

3D SDF for NP0267388 (4,4'-dihydroxybibenzyl)

3D-SDF for NP0267388 (4,4'-dihydroxybibenzyl)

PDB for NP0267388 (4,4'-dihydroxybibenzyl)

3D PDB for NP0267388 (4,4'-dihydroxybibenzyl)

SMILES for NP0267388 (4,4'-dihydroxybibenzyl)

INCHI for NP0267388 (4,4'-dihydroxybibenzyl)

Structure for NP0267388 (4,4'-dihydroxybibenzyl)

3D Structure for NP0267388 (4,4'-dihydroxybibenzyl)