NP-MRD: Showing NP-Card for methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate (NP0159265)

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Record Information

Version

2.0

Created at

2022-09-02 16:59:39 UTC

Updated at

2022-09-02 16:59:39 UTC

NP-MRD ID

NP0159265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate

Description

Methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201501122D          

 23 23  0  0  0  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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    2.0625    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    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 O   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
   -0.7145   -0.4125    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159265

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C=CC1=CC(CC=C(C)C)=C(O)C(CC=C(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-14(2)6-9-17-12-16(8-11-19(21)23-5)13-18(20(17)22)10-7-15(3)4/h6-8,11-13,22H,9-10H2,1-5H3

> <INCHI_KEY>
DKDGLQSOIBOYQO-UHFFFAOYSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.763290577901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
5.6688823263333346

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.002912041378808

> <JCHEM_PKA_STRONGEST_BASIC>
-6.058113349146049

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
98.2955

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17    7                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate

Traditional Name

methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C=CC1=CC(CC=C(C)C)=C(O)C(CC=C(C)C)=C1

InChI Identifier

InChI=1S/C20H26O3/c1-14(2)6-9-17-12-16(8-11-19(21)23-5)13-18(20(17)22)10-7-15(3)4/h6-8,11-13,22H,9-10H2,1-5H3

InChI Key

DKDGLQSOIBOYQO-UHFFFAOYSA-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 coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.47	ALOGPS
logP	5.67	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.3 m³·mol⁻¹	ChemAxon
Polarizability	36.76 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

85402151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate (NP0159265)

MOL for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

3D MOL for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

3D SDF for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

3D-SDF for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

PDB for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

3D PDB for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

SMILES for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

INCHI for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

Structure for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)

3D Structure for NP0159265 (methyl 3-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate)