NP-MRD: Showing NP-Card for Hydroxyobtustyrene (NP0084109)

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Record Information

Version

2.0

Created at

2022-04-29 04:56:41 UTC

Updated at

2022-04-29 04:56:41 UTC

NP-MRD ID

NP0084109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxyobtustyrene

Description

3-Methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. 3-Methoxy-4-benzene-1,2-diol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-methoxy-4-(3-phenylprop-2-en-1-yl)phenol. 3-Methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This hydroxylation-of-benzene-ortho-to-edg occurs in humans. Hydroxyobtustyrene is found in Dalbergia odorifera , Dalbergia parviflora and Dalbergia sissoo. It is generated by cyp1a2, cyp2c9, cyp2c19, and cyp2d6 enzymes via a hydroxylation-of-benzene-ortho-to-edg reaction.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.8380    2.5176    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533    1.1314    0.8334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592    0.2277   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -0.0924   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    0.5439   -1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996   -0.0137   -1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6475    0.6989   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    0.2162    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537    1.1108    0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    0.7573    1.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1962   -0.5729    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333   -1.4839    0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2502   -1.0982    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -1.0055   -2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -1.6230   -1.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964   -1.2976   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765   -1.9158    0.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.3791    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8404   -0.0720    1.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5300    2.7804    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    2.8788   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    3.0583    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304    1.6339   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    0.4345   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0010   -1.0632   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    1.7633   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297    2.1564    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.4949    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1218   -0.8326    1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -2.5118    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6668   -1.8071   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -1.2967   -3.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0343   -2.3515   -2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5199   -1.6637    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    0.5998    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 14  4  1  0
 13  8  1  0
  6 25  1  0
  5 23  1  0
  5 24  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 35  1  0
 17 34  1  0
 15 33  1  0
 14 32  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
M  END


  Mrv1652308211922192D          

 21 22  0  0  0  0            999 V2000
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
   -2.1434    3.7125    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.6625    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
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 H   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
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
 20  5  1  0  0  0  0
 21  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC1=C(OC)C(O)=C(O)C=C1)=C(\[H])C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-19-16-13(10-11-14(17)15(16)18)9-5-8-12-6-3-2-4-7-12/h2-8,10-11,17-18H,9H2,1H3/b8-5+

> <INCHI_KEY>
WGXMQVRYJCAUFL-VMPITWQZSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.301

> <EXACT_MASS>
256.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.824841473975027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.910153607333333

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.05720911446284

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.519727939580148

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912552596008008

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
76.53880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   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      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.336  16.170   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      -5.335  10.780   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.334  11.550   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9   20                                                  
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   12   21                                                  
CONECT    9    5   13                                                       
CONECT   10   11   13                                                       
CONECT   11   10   14                                                       
CONECT   12    6    7    8                                                  
CONECT   13    9   10   16                                                  
CONECT   14   11   15   17                                                  
CONECT   15   14   16   18                                                  
CONECT   16   13   15   19                                                  
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    1   16                                                       
CONECT   20    5                                                            
CONECT   21    8                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₃

Average Mass

256.3010 Da

Monoisotopic Mass

256.10994 Da

IUPAC Name

3-methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol

Traditional Name

3-methoxy-4-[(2E)-3-phenylprop-2-en-1-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

[H]\C(CC1=C(OC)C(O)=C(O)C=C1)=C(\[H])C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H16O3/c1-19-16-13(10-11-14(17)15(16)18)9-5-8-12-6-3-2-4-7-12/h2-8,10-11,17-18H,9H2,1H3/b8-5+

InChI Key

WGXMQVRYJCAUFL-VMPITWQZSA-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
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic 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	3.62	ALOGPS
logP	3.91	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-4.9	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	76.54 m³·mol⁻¹	ChemAxon
Polarizability	27.82 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

HMDB0130335

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9951852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11777169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hydroxyobtustyrene (NP0084109)

MOL for NP0084109 (Hydroxyobtustyrene)

3D MOL for NP0084109 (Hydroxyobtustyrene)

3D SDF for NP0084109 (Hydroxyobtustyrene)

3D-SDF for NP0084109 (Hydroxyobtustyrene)

PDB for NP0084109 (Hydroxyobtustyrene)

3D PDB for NP0084109 (Hydroxyobtustyrene)

SMILES for NP0084109 (Hydroxyobtustyrene)

INCHI for NP0084109 (Hydroxyobtustyrene)

Structure for NP0084109 (Hydroxyobtustyrene)

3D Structure for NP0084109 (Hydroxyobtustyrene)