NP-MRD: Showing NP-Card for irisquinone (NP0179007)

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Record Information

Version

2.0

Created at

2022-09-03 17:07:12 UTC

Updated at

2022-09-03 17:07:12 UTC

NP-MRD ID

NP0179007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

irisquinone

Description

Irisquinone belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. irisquinone is found in Iris pallasii and Iris pseudacorus. irisquinone was first documented in 2005 (PMID: 16011270). Based on a literature review a small amount of articles have been published on Irisquinone (PMID: 26963468) (PMID: 23276827).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219072D          

 27 27  0  0  0  0            999 V2000
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   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    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   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 23 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032219072D          

 27 27  0  0  0  0            999 V2000
   -0.7145   -1.2375    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    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   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0179007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC\C=C/CCCCCCCCCC1=CC(=O)C=C(OC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-19-22(25)20-23(27-2)24(21)26/h8-9,19-20H,3-7,10-18H2,1-2H3/b9-8-

> <INCHI_KEY>
YYCCUFKHCNSRIA-HJWRWDBZSA-N

> <FORMULA>
C24H38O3

> <MOLECULAR_WEIGHT>
374.565

> <EXACT_MASS>
374.282095084

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.86096092543036

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(10Z)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

> <JCHEM_LOGP>
7.7650109920000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.941242845221177

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
116.83709999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(10Z)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   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  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -6.160   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  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336 -13.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   18   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
6-Methoxy-2-(10-heptadecenyl)-1,4-benzoquinone	MeSH

Chemical Formula

C₂₄H₃₈O₃

Average Mass

374.5650 Da

Monoisotopic Mass

374.28210 Da

IUPAC Name

2-[(10Z)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[(10Z)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCCCC1=CC(=O)C=C(OC)C1=O

InChI Identifier

InChI=1S/C24H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-19-22(25)20-23(27-2)24(21)26/h8-9,19-20H,3-7,10-18H2,1-2H3/b9-8-

InChI Key

YYCCUFKHCNSRIA-HJWRWDBZSA-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
Iris pallasii	LOTUS Database	35616633
Iris pseudacorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Vinylogous ester
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	7.77	ChemAxon
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	16	ChemAxon
Refractivity	116.84 m³·mol⁻¹	ChemAxon
Polarizability	46.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00050849

Chemspider ID

4477043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang H, Zhang Y, Yu W, Zhao X, Xue Y, Xu H: Radiosensitizing effect of irisquinone on glioma through the downregulation of HIF-1alpha evaluated by 18F-FDG and 18F-FMISO PET/CT. Nucl Med Commun. 2016 Jul;37(7):705-14. doi: 10.1097/MNM.0000000000000498. [PubMed:26963468 ]
Xu H, Sun G, Wang H, Yue Q, Tang H, Wu Q: Dynamic observation of the radiosensitive effect of irisquinone on rabbit VX2 lung transplant tumors by using fluorine-18-deoxyglucose positron emission tomography/computed tomography. Nucl Med Commun. 2013 Mar;34(3):220-8. doi: 10.1097/MNM.0b013e32835d3730. [PubMed:23276827 ]
Zhang XN, Yan XY, Tang LH, Gong JH, Zhang Q: [Preparation, identification and inclusion actions of irisquinone hydroxypropyl-beta-cyclodextrin inclusion complex]. Yao Xue Xue Bao. 2005 Apr;40(4):369-72. [PubMed:16011270 ]
LOTUS database [Link]

Showing NP-Card for irisquinone (NP0179007)

MOL for NP0179007 (irisquinone)

3D MOL for NP0179007 (irisquinone)

3D SDF for NP0179007 (irisquinone)

3D-SDF for NP0179007 (irisquinone)

PDB for NP0179007 (irisquinone)

3D PDB for NP0179007 (irisquinone)

SMILES for NP0179007 (irisquinone)

INCHI for NP0179007 (irisquinone)

Structure for NP0179007 (irisquinone)

3D Structure for NP0179007 (irisquinone)