NP-MRD: Showing NP-Card for Honokiol (NP0084102)

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Record Information

Version

2.0

Created at

2022-04-29 04:56:27 UTC

Updated at

2022-04-29 04:56:27 UTC

NP-MRD ID

NP0084102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Honokiol

Description

Honokiol belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. Honokiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Honokiol is found in Aconitum carmichaelii, Artemisia capillaris, Chamaecyparis formosensis, Cryptomeria japonica, Illicium fargesii, Isodon flavidus, Machilus thunbergii , Magnolia obovata, Magnolia officinalis , Magnolia virginiana, Taxus mairei, Torreya nucifera and Tripterygium wilfordii. Honokiol induces caspase-dependent apoptosis in a TRAIL-mediated manner, and potentiates the pro-apoptotic effects of doxorubicin and other etoposides.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9641    0.1050   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532    0.1406   -1.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477    1.2932   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499    0.8292   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.8568    1.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309    0.4243    2.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -0.0463    2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -0.4877    3.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -0.0785    0.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -0.5749    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327   -1.7445    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -2.2510    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725   -1.6100   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328   -2.1364   -0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.4570   -0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    0.3137   -1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243    1.1465   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208    0.9818   -1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746    0.0631   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    0.3583   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   -0.7316   -1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026    0.9516   -1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -0.7123   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    1.6821   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960    2.0981   -0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.2307    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    0.4496    3.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122   -0.4632    4.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3002   -2.3036    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5715   -3.1643    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -1.7175   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -0.4332   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8999    0.9440   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2217    1.8971   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1876    0.2419   -1.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5518    1.5851   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0380    0.9931   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265    0.3260   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 15 19  1  0
 19 10  2  0
 10 11  1  0
 11 12  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  4 20  2  0
 12 13  1  0
 20  9  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 11 29  1  0
 12 30  1  0
  8 28  1  0
  6 27  1  0
  5 26  1  0
  3 24  1  0
  3 25  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
 20 38  1  0
M  END


  Mrv1533004251517012D          

 20 21  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    0.7145   -2.8875    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084102

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2

> <INCHI_KEY>
FVYXIJYOAGAUQK-UHFFFAOYSA-N

> <FORMULA>
C18H18O2

> <MOLECULAR_WEIGHT>
266.34

> <EXACT_MASS>
266.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.16982615531196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-hydroxy-3-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
5.210482000666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.53958689318358

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.839819945738014

> <JCHEM_PKA_STRONGEST_BASIC>
-6.026182953638078

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
83.73060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
honokiol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7                                                            
CONECT   11    6   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₂

Average Mass

266.3400 Da

Monoisotopic Mass

266.13068 Da

IUPAC Name

2-[4-hydroxy-3-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol

Traditional Name

honokiol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2

InChI Key

FVYXIJYOAGAUQK-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
Aconitum carmichaelii	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Illicium fargesii	LOTUS Database	35616633
Isodon flavidus	LOTUS Database	35616633
Machilus thunbergii	Plant	KNApSAcK
Magnolia obovata	LOTUS Database	35616633
Magnolia officinalis	Plant	KNApSAcK
Magnolia virginiana	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Torreya nucifera	LOTUS Database	35616633
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:5759 )
Neolignans (C10630 )

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	4.7	ALOGPS
logP	5.21	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-6	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	5	ChemAxon
Refractivity	83.73 m³·mol⁻¹	ChemAxon
Polarizability	30.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00002609

Chemspider ID

Not Available

KEGG Compound ID

C10630

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Honokiol

METLIN ID

Not Available

PubChem Compound

72303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Honokiol (NP0084102)

MOL for NP0084102 (Honokiol)

3D MOL for NP0084102 (Honokiol)

3D SDF for NP0084102 (Honokiol)

3D-SDF for NP0084102 (Honokiol)

PDB for NP0084102 (Honokiol)

3D PDB for NP0084102 (Honokiol)

SMILES for NP0084102 (Honokiol)

INCHI for NP0084102 (Honokiol)

Structure for NP0084102 (Honokiol)

3D Structure for NP0084102 (Honokiol)