NP-MRD: Showing NP-Card for 6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid (NP0049407)

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Record Information

Version

2.0

Created at

2022-03-17 21:12:03 UTC

Updated at

2022-03-17 21:12:03 UTC

NP-MRD ID

NP0049407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid

Description

6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid, also known as 3-hydroxy-5-methoxy-6-prenylstilbene-2-carboxylic acid, 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. 6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid has been detected, but not quantified in, pigeon pea and pulses. This could make 6-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311092D          

 25 26  0  0  0  0            999 V2000
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   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
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   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    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  2  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25 19  1  0  0  0  0
M  END


  Mrv0541 05061311092D          

 25 26  0  0  0  0            999 V2000
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   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
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   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    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  2  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(O)=O)C(\C=C\C2=CC=CC=C2)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O4/c1-14(2)9-11-16-17(12-10-15-7-5-4-6-8-15)20(21(23)24)18(22)13-19(16)25-3/h4-10,12-13,22H,11H2,1-3H3,(H,23,24)/b12-10+

> <INCHI_KEY>
DFMCTODOEICLEB-ZRDIBKRKSA-N

> <FORMULA>
C21H22O4

> <MOLECULAR_WEIGHT>
338.397

> <EXACT_MASS>
338.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.14532879501502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylethenyl]benzoic acid

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
5.888000171333334

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.522541216928534

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.783344210606073

> <JCHEM_PKA_STRONGEST_BASIC>
-4.868914864251974

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
101.45589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylethenyl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.003  11.550   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   25                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   11   14                                                       
CONECT   10   12   15                                                       
CONECT   11    9   16                                                       
CONECT   12   10   17                                                       
CONECT   13   18   19                                                       
CONECT   14    1    2    9                                                  
CONECT   15    7    8   10                                                  
CONECT   16   11   17   19                                                  
CONECT   17   12   16   20                                                  
CONECT   18   13   20   22                                                  
CONECT   19   13   16   25                                                  
CONECT   20   17   18   21                                                  
CONECT   21   20   23   24                                                  
CONECT   22   18                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(e)-2-phenylvinyl]benzoic acid	ChEBI
6-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(e)-2-phenylvinyl]benzoate	Generator
6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoate	Generator
3-Hydroxy-5-methoxy-6-prenylstilbene-2-carboxylic acid	HMDB
6-Hydroxy-4-methoxy-3-prenyl-2-styrylbenzoic acid	HMDB
3-Hydroxy-5-methoxy-6-prenylstilbene-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₂O₄

Average Mass

338.3970 Da

Monoisotopic Mass

338.15181 Da

IUPAC Name

6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylethenyl]benzoic acid

Traditional Name

6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylethenyl]benzoic acid

CAS Registry Number

87402-83-3

SMILES

COC1=CC(O)=C(C(O)=O)C(\C=C\C2=CC=CC=C2)=C1CC=C(C)C

InChI Identifier

InChI=1S/C21H22O4/c1-14(2)9-11-16-17(12-10-15-7-5-4-6-8-15)20(21(23)24)18(22)13-19(16)25-3/h4-10,12-13,22H,11H2,1-3H3,(H,23,24)/b12-10+

InChI Key

DFMCTODOEICLEB-ZRDIBKRKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cajanus cajan	FooDB	KNAPSACK

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
P-methoxybenzoic acid or derivatives
Methoxyphenol
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Phenol ether
Anisole
Styrene
Benzoyl
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:28152 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10264 )
Stilbenes (C10264 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090009 )

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	4.96	ALOGPS
logP	5.89	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.78	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.46 m³·mol⁻¹	ChemAxon
Polarizability	37.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039439

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281715

PDB ID

Not Available

ChEBI ID

28152

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid (NP0049407)

MOL for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

3D MOL for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

3D SDF for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

3D-SDF for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

PDB for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

3D PDB for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

SMILES for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

INCHI for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

Structure for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)

3D Structure for NP0049407 (6-Hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-2-(2-phenylethenyl)benzoic acid)