NP-MRD: Showing NP-Card for 2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one (NP0310938)

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Record Information

Version

2.0

Created at

2022-09-11 06:35:47 UTC

Updated at

2022-09-11 06:35:47 UTC

NP-MRD ID

NP0310938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one

Description

Deoxyspectinabilin belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one is found in Streptomyces spectabilis. Based on a literature review very few articles have been published on deoxyspectinabilin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112208352D          

 34 35  0  0  0  0            999 V2000
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 33  2  0  0  0  0
 33 34  1  0  0  0  0
M  CHG  2  24   1  26  -1
M  END

     RDKit          3D

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M  CHG  2  24   1  26  -1
M  END


  Mrv1652309112208352D          

 34 35  0  0  0  0            999 V2000
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M  CHG  2  24   1  26  -1
M  END
> <DATABASE_ID>
NP0310938

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C(C)=C(CC\C(C)=C\C(\C)=C\C(\C)=C\C(\C)=C\C2=CC=C(C=C2)[N+]([O-])=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO5/c1-18(8-13-26-22(5)27(30)23(6)28(33-7)34-26)14-19(2)15-20(3)16-21(4)17-24-9-11-25(12-10-24)29(31)32/h9-12,14-17H,8,13H2,1-7H3/b18-14+,19-15+,20-16+,21-17+

> <INCHI_KEY>
DNKUZPCQKAFHJN-FUPFHJOOSA-N

> <FORMULA>
C28H33NO5

> <MOLECULAR_WEIGHT>
463.574

> <EXACT_MASS>
463.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.327936873251794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxy-3,5-dimethyl-6-[(3E,5E,7E,9E)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]-4H-pyran-4-one

> <JCHEM_LOGP>
7.039049204666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.910981696707246

> <JCHEM_POLAR_SURFACE_AREA>
78.66999999999999

> <JCHEM_REFRACTIVITY>
150.44140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-3,5-dimethyl-6-[(3E,5E,7E,9E)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.674 -16.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      28.007 -19.250   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      29.341 -18.480   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      28.007 -20.790   0.000  0.00  0.00           O-1
HETATM   27  C   UNK     0      25.340 -19.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.006 -18.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   20                                                       
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃NO₅

Average Mass

463.5740 Da

Monoisotopic Mass

463.23587 Da

IUPAC Name

2-methoxy-3,5-dimethyl-6-[(3E,5E,7E,9E)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]-4H-pyran-4-one

Traditional Name

2-methoxy-3,5-dimethyl-6-[(3E,5E,7E,9E)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C(C)=C(CC\C(C)=C\C(\C)=C\C(\C)=C\C(\C)=C\C2=CC=C(C=C2)[N+]([O-])=O)O1

InChI Identifier

InChI=1S/C28H33NO5/c1-18(8-13-26-22(5)27(30)23(6)28(33-7)34-26)14-19(2)15-20(3)16-21(4)17-24-9-11-25(12-10-24)29(31)32/h9-12,14-17H,8,13H2,1-7H3/b18-14+,19-15+,20-16+,21-17+

InChI Key

DNKUZPCQKAFHJN-FUPFHJOOSA-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
Streptomyces spectabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Aromatic monoterpenoid
Nitrobenzene
Nitroaromatic compound
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Organic nitro compound
Cyclic ketone
C-nitro compound
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	7.04	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.67 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	150.44 m³·mol⁻¹	ChemAxon
Polarizability	53.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

76962515

KEGG Compound ID

Not Available

BioCyc ID

CPD-21836

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122606041

PDB ID

Not Available

ChEBI ID

142843

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one (NP0310938)

MOL for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

3D MOL for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

3D SDF for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

3D-SDF for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

PDB for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

3D PDB for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

SMILES for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

INCHI for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

Structure for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)

3D Structure for NP0310938 (2-methoxy-3,5-dimethyl-6-[(3e,5e,7e,9e)-3,5,7,9-tetramethyl-10-(4-nitrophenyl)deca-3,5,7,9-tetraen-1-yl]pyran-4-one)