NP-MRD: Showing NP-Card for 2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate (NP0318276)

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Record Information

Version

2.0

Created at

2022-09-11 18:40:39 UTC

Updated at

2022-09-11 18:40:39 UTC

NP-MRD ID

NP0318276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate

Description

2-Methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate is found in Helichrysum asperum and Helichrysum caespititium. 2-Methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241508482D          

 23 23  0  0  0  0            999 V2000
    1.4289    3.3000    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
    2.1434    2.0625    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
    0.0000    2.4750    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
    2.1434    1.2375    0.0000 O   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 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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -1.4289   -2.4750    0.0000 C   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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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  1  0  0  0  0
 14 13  1  4  0  0  0
 14 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
 19 21  1  0  0  0  0
 12 22  2  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)COC(C)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-9(2)16(21)15-14(20)7-13(19)12(17(15)22)6-5-10(3)8-23-11(4)18/h5,7,9,19-20,22H,6,8H2,1-4H3

> <INCHI_KEY>
WHQQRQUYKZUAEE-UHFFFAOYSA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.55017067919472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
4.052640747999999

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.553770917139358

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.784273601868163

> <JCHEM_PKA_STRONGEST_BASIC>
-4.611527562645544

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
86.7739

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+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  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   12    6   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetic acid	Generator
2-Methyl-4-[2',4',6'-trihydroxy-3'-(2-methyl-propanoyl)phenyl]but-2-enyl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₆

Average Mass

322.3570 Da

Monoisotopic Mass

322.14164 Da

IUPAC Name

2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate

Traditional Name

2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)COC(C)=O)=C1O

InChI Identifier

InChI=1S/C17H22O6/c1-9(2)16(21)15-14(20)7-13(19)12(17(15)22)6-5-10(3)8-23-11(4)18/h5,7,9,19-20,22H,6,8H2,1-4H3

InChI Key

WHQQRQUYKZUAEE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helichrysum asperum	LOTUS Database	35616633
Helichrysum caespititium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Phenylpropane
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	2.69	ALOGPS
logP	4.05	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.77 m³·mol⁻¹	ChemAxon
Polarizability	33.55 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

85040309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate (NP0318276)

MOL for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

3D MOL for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

3D SDF for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

3D-SDF for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

PDB for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

3D PDB for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

SMILES for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

INCHI for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

Structure for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)

3D Structure for NP0318276 (2-methyl-4-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl]but-2-en-1-yl acetate)