NP-MRD: Showing NP-Card for 5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol (NP0335656)

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Record Information

Version

2.0

Created at

2024-09-11 02:37:00 UTC

Updated at

2024-09-11 02:37:01 UTC

NP-MRD ID

NP0335656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol

Description

5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol, also known as 4-(3-methyl-1-butenyl)-3,4',5-trihydroxystilbene, 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. 5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol has been detected, but not quantified in, nuts. This could make 5-[(4-hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209472D          

 22 23  0  0  0  0            999 V2000
   -1.0721    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  2  0  0  0  0
  2 17  2  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
  4 22  1  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\C=C\C1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-13(2)3-10-17-18(21)11-15(12-19(17)22)5-4-14-6-8-16(20)9-7-14/h3-13,20-22H,1-2H3/b5-4-,10-3+

> <INCHI_KEY>
XTDKVQYWANHUFS-MZTCIMCMSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.3603

> <EXACT_MASS>
296.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.14950686803124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-[(1E)-3-methylbut-1-en-1-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
5.257315710333334

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.591468428185303

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.955060887987804

> <JCHEM_PKA_STRONGEST_BASIC>
-5.745719829323794

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
91.9649

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-[(1E)-3-methylbut-1-en-1-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.001   4.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.387   3.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.387  -2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -3.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.617  -2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.769  -3.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001  -2.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.619  -2.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.387  -3.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.387  -4.619   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.769  -0.001   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.617  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.001  -0.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.387  -0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.619  -0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.619   1.539   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.387   2.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.001   1.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.617   2.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.617   3.849   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.769   4.619   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.001  -4.619   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1   17                                                       
CONECT    3    4   14                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    7    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    5   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    2   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    1   19   21                                                  
CONECT   21   20                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
4-(3-Methyl-1-butenyl)-3,4',5-trihydroxystilbene	HMDB

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3603 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-[(1E)-3-methylbut-1-en-1-yl]benzene-1,3-diol

Traditional Name

5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-[(1E)-3-methylbut-1-en-1-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

CC(C)\C=C\C1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C19H20O3/c1-13(2)3-10-17-18(21)11-15(12-19(17)22)5-4-14-6-8-16(20)9-7-14/h3-13,20-22H,1-2H3/b5-4-,10-3+

InChI Key

XTDKVQYWANHUFS-MZTCIMCMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Styrene
Resorcinol
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

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	4.28	ALOGPS
logP	5.26	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.96 m³·mol⁻¹	ChemAxon
Polarizability	33.15 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

HMDB0030599

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002493

KNApSAcK ID

C00015528

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol (NP0335656)

MOL for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

3D MOL for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

3D SDF for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

3D-SDF for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

PDB for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

3D PDB for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

SMILES for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

INCHI for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

Structure for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)

3D Structure for NP0335656 (5-[(4-Hydroxypheny)ethenyl]-2-(3-methyl-1-butenyl)-1,3-benzenediol)