NP-MRD: Showing NP-Card for 3,6-Dimethoxy-4-hydroxyphenanthrene (NP0061159)

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Record Information

Version

2.0

Created at

2022-04-28 06:03:12 UTC

Updated at

2022-04-28 06:03:13 UTC

NP-MRD ID

NP0061159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6-Dimethoxy-4-hydroxyphenanthrene

Description

3,6-Dimethoxy-4-phenanthrenol, also known as alpha-thebaol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 3,6-Dimethoxy-4-phenanthrenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,6-Dimethoxy-4-phenanthrenol has been detected, but not quantified in, opium poppies. 3,6-Dimethoxy-4-hydroxyphenanthrene is found in Combretum hereroense , Papaver bracteatum and Papaver somniferum . This could make 3,6-dimethoxy-4-phenanthrenol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.0403   -1.5885   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6310   -1.6298   -0.1772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -0.4859    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609    0.7440    0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    1.8559    0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976    1.7541    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5491    2.8970    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8116    2.7863    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    1.5701    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    1.4923    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348    0.2774    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005   -0.8692   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -2.0604   -0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7530   -2.1989   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014   -0.7882   -0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663   -1.9686   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733    0.4043    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    0.5032    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779   -0.6181    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -0.7564   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527   -1.4736    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -2.5777   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5385    0.7846    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1432    2.8111    0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463    3.8518    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373    3.6673    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3587    2.4087    0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147    0.2629    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1470   -1.4544   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2252   -1.9490    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290   -3.1919   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -2.8578   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984   -1.6027   -0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 18  1  0
 18  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 17  2  0
 17 15  1  0
 15 16  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 10  2  0
  4  3  1  0
 10  9  1  0
 17 18  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 33  1  0
  5 24  1  0
  4 23  1  0
  7 25  1  0
  8 26  1  0
 16 32  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 11 28  1  0
 10 27  1  0
M  END


  Mrv0541 02241220132D          

 19 21  0  0  0  0            999 V2000
   -2.0623    0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249    1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0623    0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0623   -1.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623   -1.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 14  2  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
  6 15  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  2  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C=CC1=C2C(O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-18-12-7-5-10-3-4-11-6-8-14(19-2)16(17)15(11)13(10)9-12/h3-9,17H,1-2H3

> <INCHI_KEY>
GKDSKCYMUUXQLA-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.2806

> <EXACT_MASS>
254.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.35752733259887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dimethoxyphenanthren-4-ol

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.333291476333333

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.4277241625233

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5597038905552285

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
73.8657

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dimethoxyphenanthren-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.850   0.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080   2.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   2.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   3.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   3.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   2.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080   2.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   0.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -0.665   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.850  -1.999   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.850  -1.999   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.080  -0.665   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540  -0.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770   0.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.770   0.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540  -0.665   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.770  -1.999   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.080  -3.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.080  -3.334   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   18                                                       
CONECT   11   12   19                                                       
CONECT   12    1   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15    6   14   16                                                  
CONECT   16    9   15   17                                                  
CONECT   17   16                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
3,6-Dimethoxy-4-hydroxyphenanthrene	HMDB
3,6-Dimethoxy-4-phenanthrenol, 9ci	HMDB
3,6-Dimethoxy-4-phenanthrol	HMDB
alpha-Thebaol	HMDB
Thebaol	HMDB

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2806 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

3,6-dimethoxyphenanthren-4-ol

Traditional Name

3,6-dimethoxyphenanthren-4-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C=CC1=C2C(O)=C(OC)C=C1

InChI Identifier

InChI=1S/C16H14O3/c1-18-12-7-5-10-3-4-11-6-8-14(19-2)16(17)15(11)13(10)9-12/h3-9,17H,1-2H3

InChI Key

GKDSKCYMUUXQLA-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
Combretum hereroense	Plant	KNApSAcK
Papaver bracteatum	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
1-naphthol
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.53	ALOGPS
logP	3.33	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.43	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.87 m³·mol⁻¹	ChemAxon
Polarizability	27.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000873

KNApSAcK ID

C00015402

Chemspider ID

536624

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

617472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,6-Dimethoxy-4-hydroxyphenanthrene (NP0061159)

MOL for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

3D MOL for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

3D SDF for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

3D-SDF for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

PDB for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

3D PDB for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

SMILES for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

INCHI for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

Structure for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)

3D Structure for NP0061159 (3,6-Dimethoxy-4-hydroxyphenanthrene)