NP-MRD: Showing NP-Card for 2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate (NP0330526)

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Record Information

Version

2.0

Created at

2022-09-12 15:57:50 UTC

Updated at

2022-09-12 15:57:51 UTC

NP-MRD ID

NP0330526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate

Description

2-(1-Hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. 2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate is found in Eupatorium fortunei. 2-(1-Hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231523582D          

 20 20  0  0  0  0            999 V2000
   -0.5230    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 O   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
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
    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    0.8250    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
   -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 O   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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(CO)C1=CC=C(C)C=C1OC(=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O4/c1-11(2)8-15(18)20-14-9-12(3)6-7-13(14)16(4,10-17)19-5/h6-9,17H,10H2,1-5H3

> <INCHI_KEY>
VCMSRECHCNEQOQ-UHFFFAOYSA-N

> <FORMULA>
C16H22O4

> <MOLECULAR_WEIGHT>
278.348

> <EXACT_MASS>
278.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.882566666348428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
3.2395692489999997

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.211027343610581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.143896639904731

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
79.0026

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.976   5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-(1-Hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoic acid	Generator
3-Methyl-2-butenoate 2-(1-methyl-1-methoxy-2-hydroxyethyl)-5-methylphenyl ester	Generator

Chemical Formula

C₁₆H₂₂O₄

Average Mass

278.3480 Da

Monoisotopic Mass

278.15181 Da

IUPAC Name

2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate

Traditional Name

2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC(C)(CO)C1=CC=C(C)C=C1OC(=O)C=C(C)C

InChI Identifier

InChI=1S/C16H22O4/c1-11(2)8-15(18)20-14-9-12(3)6-7-13(14)16(4,10-17)19-5/h6-9,17H,10H2,1-5H3

InChI Key

VCMSRECHCNEQOQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium fortunei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Benzylether
Phenoxy compound
Toluene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Organic oxide
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	2.87	ALOGPS
logP	3.24	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79 m³·mol⁻¹	ChemAxon
Polarizability	30.88 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

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

11119408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate (NP0330526)

MOL for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

3D MOL for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

3D SDF for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

3D-SDF for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

PDB for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

3D PDB for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

SMILES for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

INCHI for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

Structure for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)

3D Structure for NP0330526 (2-(1-hydroxy-2-methoxypropan-2-yl)-5-methylphenyl 3-methylbut-2-enoate)