NP-MRD: Showing NP-Card for 1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone (NP0221271)

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Record Information

Version

2.0

Created at

2022-09-05 22:47:59 UTC

Updated at

2022-09-05 22:47:59 UTC

NP-MRD ID

NP0221271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone

Description

1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone is found in Artemisia monosperma.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200482D          

 21 21  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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
    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
   -1.4289   -1.6500    0.0000 O   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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  2  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C(C\C=C(\C)CO)=CC(=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O3/c1-12(2)5-7-15-9-17(14(4)20)10-16(18(15)21)8-6-13(3)11-19/h5-6,9-10,19,21H,7-8,11H2,1-4H3/b13-6-

> <INCHI_KEY>
RCCPQGOKROXSMK-MLPAPPSSSA-N

> <FORMULA>
C18H24O3

> <MOLECULAR_WEIGHT>
288.387

> <EXACT_MASS>
288.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.921896463848995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{4-hydroxy-3-[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethan-1-one

> <JCHEM_LOGP>
3.4036908550000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.153012874591038

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.397461731656933

> <JCHEM_PKA_STRONGEST_BASIC>
-2.725800720023403

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
88.702

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-{4-hydroxy-3-[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   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  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   14    4                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄O₃

Average Mass

288.3870 Da

Monoisotopic Mass

288.17254 Da

IUPAC Name

1-{4-hydroxy-3-[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethan-1-one

Traditional Name

1-{4-hydroxy-3-[(2Z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C(C\C=C(\C)CO)=CC(=C1)C(C)=O

InChI Identifier

InChI=1S/C18H24O3/c1-12(2)5-7-15-9-17(14(4)20)10-16(18(15)21)8-6-13(3)11-19/h5-6,9-10,19,21H,7-8,11H2,1-4H3/b13-6-

InChI Key

RCCPQGOKROXSMK-MLPAPPSSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia monosperma	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.4	ChemAxon
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88.7 m³·mol⁻¹	ChemAxon
Polarizability	32.92 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone (NP0221271)

MOL for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

3D MOL for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

3D SDF for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

3D-SDF for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

PDB for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

3D PDB for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

SMILES for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

INCHI for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

Structure for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)

3D Structure for NP0221271 (1-{4-hydroxy-3-[(2z)-4-hydroxy-3-methylbut-2-en-1-yl]-5-(3-methylbut-2-en-1-yl)phenyl}ethanone)