NP-MRD: Showing NP-Card for 3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid (NP0176575)

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Record Information

Version

2.0

Created at

2022-09-03 14:15:53 UTC

Updated at

2022-09-03 14:15:53 UTC

NP-MRD ID

NP0176575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Description

3-(2-Hydroxy-4-methoxyphenyl)prop-2-enoic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid is found in Artemisia dracunculus. 3-(2-Hydroxy-4-methoxyphenyl)prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652308231914572D          

 14 14  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.8250    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
    0.0000    0.8250    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
    0.0000    0.0000    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
  5 10  1  4  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=CC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-14-8-4-2-7(9(11)6-8)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)

> <INCHI_KEY>
IKNVEOZIOFMENG-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.342639803977857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.6748496726666668

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.258199436750106

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9659345650256013

> <JCHEM_PKA_STRONGEST_BASIC>
-4.83290525342976

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.50400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    8    9                                                       
CONECT    7    2    3    9                                                  
CONECT    8    4    6   14                                                  
CONECT    9    6    7   11                                                  
CONECT   10    5   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    1    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-(2-Hydroxy-4-methoxyphenyl)prop-2-enoate	Generator

Chemical Formula

C₁₀H₁₀O₄

Average Mass

194.1860 Da

Monoisotopic Mass

194.05791 Da

IUPAC Name

3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Traditional Name

3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=CC(O)=O)C=C1

InChI Identifier

InChI=1S/C10H10O4/c1-14-8-4-2-7(9(11)6-8)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)

InChI Key

IKNVEOZIOFMENG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia dracunculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Anisole
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	1.59	ALOGPS
logP	1.67	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
pKa (Strongest Basic)	-4.8	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	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.34 Å³	ChemAxon
Number of Rings	1	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

HMDB0135741

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB092705

KNApSAcK ID

Not Available

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

20985633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid (NP0176575)

MOL for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

3D MOL for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

3D SDF for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

3D-SDF for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

PDB for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

3D PDB for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

SMILES for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

INCHI for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

Structure for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)

3D Structure for NP0176575 (3-(2-hydroxy-4-methoxyphenyl)prop-2-enoic acid)