NP-MRD: Showing NP-Card for Obtusaquinone (NP0063773)

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Record Information

Version

2.0

Created at

2022-04-28 08:07:01 UTC

Updated at

2022-04-28 08:07:01 UTC

NP-MRD ID

NP0063773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Obtusaquinone

Description

Obtusaquinone belongs to the class of organic compounds known as p-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 4, respectively. Obtusaquinone is found in Dalbergia retusa. Obtusaquinone was first documented in 2004 (PMID: 15081296). Based on a literature review a small amount of articles have been published on Obtusaquinone (PMID: 33134921) (PMID: 32338864) (PMID: 23479453) (PMID: 16242087).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.2347   -2.3317    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789   -1.3881    0.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1712   -0.1164    0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1599    0.7246    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9196    2.1090   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646    2.9054   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    2.5456   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3206    3.8368   -0.9602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    1.7168   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    0.3505    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615   -0.4435    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -0.0710    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434   -0.9919    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9420   -0.6891    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517    0.5077   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098    0.7241   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -0.3035   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1785   -1.5148    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406   -1.7335    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189   -3.2951    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2716   -1.9911    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088   -2.5557   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1740    0.4163    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708    4.2838   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    2.1094   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -1.4622    0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020    0.8950   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327   -1.9784    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    1.3173   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    1.6671   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7458   -0.1924   -0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530   -2.3506    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -2.7008    0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10  3  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652304282210072D          

 19 20  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   -2.8875    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
    1.4289   -4.1250    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
    2.1434   -2.8875    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
    2.8579   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
   -0.7145   -2.8875    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
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  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
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(O)=C\C1=C/C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-19-16-11-15(18)14(17)10-13(16)9-5-8-12-6-3-2-4-7-12/h2-11,17H,1H3/b8-5+,13-9+

> <INCHI_KEY>
LUZUAYAKZLCOCQ-BHHNFLQBSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.609093497193374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-2-hydroxy-5-methoxy-4-[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.476891979

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.321114048692102

> <JCHEM_PKA_STRONGEST_BASIC>
-3.651204715107359

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
79.45810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-2-hydroxy-5-methoxy-4-[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-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  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2   15   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    3   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    1   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Obtusaquinone, (e,e)-isomer	MeSH

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

(4E)-2-hydroxy-5-methoxy-4-[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexa-2,5-dien-1-one

Traditional Name

(4E)-2-hydroxy-5-methoxy-4-[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(O)=C\C1=C/C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O3/c1-19-16-11-15(18)14(17)10-13(16)9-5-8-12-6-3-2-4-7-12/h2-11,17H,1H3/b8-5+,13-9+

InChI Key

LUZUAYAKZLCOCQ-BHHNFLQBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 retusa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 4, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-quinomethanes

Alternative Parents

Substituents

Styrene
P-quinomethane
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Enol
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	2.89	ALOGPS
logP	2.48	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.46 m³·mol⁻¹	ChemAxon
Polarizability	27.61 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

C00020661

Chemspider ID

4765897

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5967872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Teng J, Lashgari G, Tabet EI, Tannous BA: The natural compound obtusaquinone targets pediatric high-grade gliomas through ROS-mediated ER stress. Neurooncol Adv. 2020 Aug 27;2(1):vdaa106. doi: 10.1093/noajnl/vdaa106. eCollection 2020 Jan-Dec. [PubMed:33134921 ]
Badr CE, da Hora CC, Kirov AB, Tabet E, Amante R, Maksoud S, Nibbs AE, Fitzsimons E, Boukhali M, Chen JW, Chiu NHL, Nakano I, Haas W, Mazitschek R, Tannous BA: Obtusaquinone: A Cysteine-Modifying Compound That Targets Keap1 for Degradation. ACS Chem Biol. 2020 Jun 19;15(6):1445-1454. doi: 10.1021/acschembio.0c00104. Epub 2020 May 8. [PubMed:32338864 ]
Badr CE, Van Hoppe S, Dumbuya H, Tjon-Kon-Fat LA, Tannous BA: Targeting cancer cells with the natural compound obtusaquinone. J Natl Cancer Inst. 2013 May 1;105(9):643-53. doi: 10.1093/jnci/djt037. Epub 2013 Mar 11. [PubMed:23479453 ]
Moratinos MM, Tevar E, Conde-Salazar L: Contact allergy to a cocobolo bracelet. Dermatitis. 2005 Sep;16(3):139-41. [PubMed:16242087 ]
Barragan-Huerta BE, Peralta-Cruz J, Gonzalez-Laredo RF, Karchesy J: Neocandenatone, an isoflavan-cinnamylphenol quinone methide pigment from Dalbergia congestiflora. Phytochemistry. 2004 Apr;65(7):925-8. doi: 10.1016/j.phytochem.2003.11.011. [PubMed:15081296 ]

Showing NP-Card for Obtusaquinone (NP0063773)

MOL for NP0063773 (Obtusaquinone)

3D MOL for NP0063773 (Obtusaquinone)

3D SDF for NP0063773 (Obtusaquinone)

3D-SDF for NP0063773 (Obtusaquinone)

PDB for NP0063773 (Obtusaquinone)

3D PDB for NP0063773 (Obtusaquinone)

SMILES for NP0063773 (Obtusaquinone)

INCHI for NP0063773 (Obtusaquinone)

Structure for NP0063773 (Obtusaquinone)

3D Structure for NP0063773 (Obtusaquinone)