NP-MRD: Showing NP-Card for 2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one (NP0263876)

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Record Information

Version

2.0

Created at

2022-09-08 07:12:22 UTC

Updated at

2022-09-08 07:12:22 UTC

NP-MRD ID

NP0263876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one

Description

Stigmatellin belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. 2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one was first documented in 2020 (PMID: 31971990). Based on a literature review a small amount of articles have been published on stigmatellin (PMID: 35889529) (PMID: 35355286) (PMID: 34299598) (PMID: 32930405).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082209122D          

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M  END

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M  END


  Mrv1652309082209122D          

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    9.6877   -6.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -6.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -7.7564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -6.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -6.5091    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
  3  4  1  0  0  0  0
  3  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  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  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
 14 17  1  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 21 36  2  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(\C=C\C=C\C(\C)=C/C)C(C)C(OC)C(C)CCC1=C(C)C(=O)C2=C(OC)C=C(OC)C(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10-

> <INCHI_KEY>
UZHDGDDPOPDJGM-XSEAFXJRSA-N

> <FORMULA>
C30H42O7

> <MOLECULAR_WEIGHT>
514.659

> <EXACT_MASS>
514.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.69828273933878

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(7E,9E,11Z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-chromen-4-one

> <JCHEM_LOGP>
5.658795710333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.058062551144655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.760068190844964

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
150.67020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(7E,9E,11Z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.506   0.364   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.994   0.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.490  -1.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.978  -1.673   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.498  -2.546   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.994  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -5.166   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.498  -6.621   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.506  -7.785   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.490  -9.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.018  -7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.522  -6.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.027  -8.658   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.522 -10.113   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.531 -11.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.539  -8.367   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.043  -6.912   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.547  -9.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.059  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.067 -10.404   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.580 -10.113   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.588 -11.277   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.100 -10.986   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.604  -9.531   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.108 -12.150   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      22.620 -11.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      23.629 -13.023   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.604 -13.605   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.092 -13.897   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      18.588 -15.352   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.076 -15.643   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.084 -12.732   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.571 -13.023   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.067 -14.479   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      15.563 -11.859   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.051 -12.150   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   23   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   21   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₇

Average Mass

514.6590 Da

Monoisotopic Mass

514.29305 Da

IUPAC Name

2-[(7E,9E,11Z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-chromen-4-one

Traditional Name

2-[(7E,9E,11Z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one

CAS Registry Number

Not Available

SMILES

COC(\C=C\C=C\C(\C)=C/C)C(C)C(OC)C(C)CCC1=C(C)C(=O)C2=C(OC)C=C(OC)C(O)=C2O1

InChI Identifier

InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10-

InChI Key

UZHDGDDPOPDJGM-XSEAFXJRSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Anisole
Phenol ether
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Dialkyl ether
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.66	ChemAxon
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	150.67 m³·mol⁻¹	ChemAxon
Polarizability	58.7 Å³	ChemAxon
Number of Rings	2	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

C00018584

Chemspider ID

4940265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stigmatellin

METLIN ID

Not Available

PubChem Compound

6435507

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Okoth DA, Hug JJ, Garcia R, Muller R: Three New Stigmatellin Derivatives Reveal Biosynthetic Insights of Its Side Chain Decoration. Molecules. 2022 Jul 21;27(14):4656. doi: 10.3390/molecules27144656. [PubMed:35889529 ]
Boopathi S, Vashisth R, Mohanty AK, Jia AQ, Sivakumar N, Arockiaraj J: Bacillus subtilis BR4 derived stigmatellin Y interferes Pqs-PqsR mediated quorum sensing system of Pseudomonas aeruginosa. J Basic Microbiol. 2022 Jul;62(7):801-814. doi: 10.1002/jobm.202200017. Epub 2022 Mar 30. [PubMed:35355286 ]
Jovic O, Smuc T: Search for Novel Lead Inhibitors of Yeast Cytochrome bc1, from Drugbank and COCONUT. Molecules. 2021 Jul 16;26(14):4323. doi: 10.3390/molecules26144323. [PubMed:34299598 ]
Gao M, Qin Y, Li A, Wei S, Liu B, Tian X, Gong G: Mitoflash generated at the Qo site of mitochondrial Complex III. J Cell Physiol. 2021 Apr;236(4):2920-2933. doi: 10.1002/jcp.30059. Epub 2020 Sep 15. [PubMed:32930405 ]
Lupien A, Foo CS, Savina S, Vocat A, Piton J, Monakhova N, Benjak A, Lamprecht DA, Steyn AJC, Pethe K, Makarov VA, Cole ST: New 2-Ethylthio-4-methylaminoquinazoline derivatives inhibiting two subunits of cytochrome bc1 in Mycobacterium tuberculosis. PLoS Pathog. 2020 Jan 23;16(1):e1008270. doi: 10.1371/journal.ppat.1008270. eCollection 2020 Jan. [PubMed:31971990 ]
LOTUS database [Link]

Showing NP-Card for 2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one (NP0263876)

MOL for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

3D MOL for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

3D SDF for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

3D-SDF for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

PDB for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

3D PDB for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

SMILES for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

INCHI for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

Structure for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)

3D Structure for NP0263876 (2-[(7e,9e,11z)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one)