NP-MRD: Showing NP-Card for (2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one (NP0147671)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 03:19:19 UTC

Updated at

2022-09-02 03:19:19 UTC

NP-MRD ID

NP0147671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one

Description

Isocymopolone belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain. (2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one is found in Cymopolia barbata. Based on a literature review very few articles have been published on Isocymopolone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.8468    0.3175    1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4649    0.3616   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5411    0.2097   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.5342   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838    0.6759    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831   -0.4259    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.6197   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559   -1.0467   -1.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -0.4710   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -0.1037    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1713    0.1250    1.7569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466    0.0330    0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8736   -0.1934   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468   -0.0792   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9107   -0.3137   -1.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9617    0.2703    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8833    0.4377    0.4239 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.2924    0.4979    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8809    0.3839    1.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    0.6354    2.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6395    1.2763    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910   -0.4816    1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9117    0.0631    1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3317   -0.4179   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790   -0.2942   -1.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8884    1.2313   -1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.5689   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6444    0.6886    1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7379    1.6884    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143   -1.3628    0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7657   -0.6581    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309   -1.4984   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498   -1.8783   -2.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979   -0.2249   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -0.6465   -1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -0.4710   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8946   -0.2324   -1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8592    0.7769    2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    0.6439    3.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 15 37  1  0
 18 38  1  0
 20 39  1  0
M  END


  Mrv1652309022205192D          

 20 20  0  0  0  0            999 V2000
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   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 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    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 O   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 Br  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  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
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C/C(=O)C1=CC(O)=C(Br)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19BrO3/c1-10(2)5-4-6-11(3)7-14(18)12-8-16(20)13(17)9-15(12)19/h5,7-9,19-20H,4,6H2,1-3H3/b11-7-

> <INCHI_KEY>
VJTRXVYGZCUUJN-XFFZJAGNSA-N

> <FORMULA>
C16H19BrO3

> <MOLECULAR_WEIGHT>
339.229

> <EXACT_MASS>
338.051757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.00982412093766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
5.388518865

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.317176239073545

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.988296033281719

> <JCHEM_PKA_STRONGEST_BASIC>
-6.640833384911699

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.4512

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       1.334  -2.310   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  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                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉BrO₃

Average Mass

339.2290 Da

Monoisotopic Mass

338.05176 Da

IUPAC Name

(2Z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one

Traditional Name

(2Z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C/C(=O)C1=CC(O)=C(Br)C=C1O

InChI Identifier

InChI=1S/C16H19BrO3/c1-10(2)5-4-6-11(3)7-14(18)12-8-16(20)13(17)9-15(12)19/h5,7-9,19-20H,4,6H2,1-3H3/b11-7-

InChI Key

VJTRXVYGZCUUJN-XFFZJAGNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cymopolia barbata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylated hydroquinones

Alternative Parents

Substituents

Prenylbenzoquinol
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
1,4-dihydroxy-2-halobenzenoid
Benzoyl
3-halophenol
2-halophenol
Hydroquinone
3-bromophenol
2-bromophenol
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Halobenzene
Bromobenzene
Monocyclic benzene moiety
Benzenoid
Aryl halide
Aryl bromide
Vinylogous acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Ketone
Organobromide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organohalogen 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	4.15	ALOGPS
logP	5.39	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.45 m³·mol⁻¹	ChemAxon
Polarizability	32.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

10269365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13893962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one (NP0147671)

MOL for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

3D MOL for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

3D SDF for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

3D-SDF for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

PDB for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

3D PDB for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

SMILES for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

INCHI for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

Structure for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)

3D Structure for NP0147671 ((2z)-1-(4-bromo-2,5-dihydroxyphenyl)-3,7-dimethylocta-2,6-dien-1-one)