NP-MRD: Showing NP-Card for 2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione (NP0153194)

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Record Information

Version

2.0

Created at

2022-09-02 09:48:35 UTC

Updated at

2022-09-02 09:48:35 UTC

NP-MRD ID

NP0153194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

Description

(S)-4-Methoxydalbergione belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2. 2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione is found in Dalbergia baronii, Dalbergia cearensis, Dalbergia cultrata, Dalbergia inundata, Dalbergia latifolia, Dalbergia melanoxylon, Dalbergia miscolobium, Dalbergia nitidula, Dalbergia odorifera, Dalbergia riparia, Dalbergia sissoo, Dalbergia spruceana and Dalbergia stevensonii. 2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione was first documented in 2015 (PMID: 25766504). Based on a literature review very few articles have been published on (S)-4-Methoxydalbergione (PMID: 31826027).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.9754   -3.1168   -0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -2.2577   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275   -0.9096   -0.7292 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4335   -0.4747   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759   -0.2534   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    0.1704   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    0.3650   -1.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    0.3636    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3179    0.7708    1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    0.9575    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    0.1455    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733   -0.2815    1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -0.4714    2.0096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    0.0800   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -0.1665    0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6711    0.7208    1.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8554    1.8995    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    2.1640   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1348    1.2417   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1527   -4.1077   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.8511   -1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027   -2.5699    0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -0.9004   -1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -0.3837   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026    0.0038   -0.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758    1.7795   -0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    1.1723    0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264    0.2807    2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974   -1.0708    1.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741    0.5307    2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5901    2.6481    0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2273    3.0890   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445    1.4321   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6  8  1  0
 19 14  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
  5 24  1  0
  3 23  1  6
  2 22  1  0
  1 20  1  0
  1 21  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652309022211482D          

 19 20  0  0  1  0            999 V2000
    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  2  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
    2.8579   -1.6500    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
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   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
    2.8579    0.8250    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
    4.2868    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  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
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(=CC1=O)[C@@H](C=C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-10,12H,1H2,2H3/t12-/m0/s1

> <INCHI_KEY>
RGSUZUQISVAJJF-LBPRGKRZSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.593659367716256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-5-[(1S)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.019806421333333

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.940178735594977

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
75.99420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-5-[(1S)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

> <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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14    3   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

2-methoxy-5-[(1S)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

2-methoxy-5-[(1S)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(=CC1=O)[C@@H](C=C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-10,12H,1H2,2H3/t12-/m0/s1

InChI Key

RGSUZUQISVAJJF-LBPRGKRZSA-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
Dalbergia baronii	LOTUS Database	35616633
Dalbergia cearensis	LOTUS Database	35616633
Dalbergia cultrata	LOTUS Database	35616633
Dalbergia inundata	LOTUS Database	35616633
Dalbergia latifolia	LOTUS Database	35616633
Dalbergia melanoxylon	LOTUS Database	35616633
Dalbergia miscolobium	LOTUS Database	35616633
Dalbergia nitidula	LOTUS Database	35616633
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia riparia	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dalbergia spruceana	LOTUS Database	35616633
Dalbergia stevensonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Dalbergiones

Direct Parent

Dalbergiones

Alternative Parents

Substituents

Dalbergione skeleton
Quinone
P-benzoquinone
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.65	ALOGPS
logP	3.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.99 m³·mol⁻¹	ChemAxon
Polarizability	26.59 Å³	ChemAxon
Number of Rings	2	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

C00010252

Chemspider ID

8575492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10400054

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pfohler C, Tilgen W: Contact dermatitis of the lips due to late-type sensitization against dalbergiones in a wooden recorder. Allergol Select. 2018 Sep 1;2(1):29-31. doi: 10.5414/ALX01323E. eCollection 2018. [PubMed:31826027 ]
Caruana L, Mondatori M, Corti V, Morales S, Mazzanti A, Fochi M, Bernardi L: Catalytic asymmetric addition of Meldrum's acid, malononitrile, and 1,3-dicarbonyls to ortho-quinone methides generated in situ under basic conditions. Chemistry. 2015 Apr 13;21(16):6037-41. doi: 10.1002/chem.201500710. Epub 2015 Mar 12. [PubMed:25766504 ]
LOTUS database [Link]

Showing NP-Card for 2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione (NP0153194)

MOL for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

PDB for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

SMILES for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

INCHI for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

Structure for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0153194 (2-methoxy-5-[(1s)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione)