NP-MRD: Showing NP-Card for 7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate (NP0200115)

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Record Information

Version

2.0

Created at

2022-09-04 18:53:21 UTC

Updated at

2022-09-04 18:53:21 UTC

NP-MRD ID

NP0200115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate

Description

7-(Furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]Heptadec-12-en-2-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate is found in Aster verticillatus. 7-(Furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]Heptadec-12-en-2-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505522D          

 33 37  0  0  0  0            999 V2000
    4.1644    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    2.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    2.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7746    3.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044    2.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095    2.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    1.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    1.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892    0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593    2.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167    0.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0140   -0.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -1.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4896    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1740   -0.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0210   -1.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227   -1.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
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  3  5  1  0  0  0  0
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 32 33  2  0  0  0  0
 29 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004201505522D          

 33 37  0  0  0  0            999 V2000
    4.1644    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    2.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    2.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7746    3.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044    2.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095    2.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0200115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CC2C(=O)OC(CC2(C)C2C(=O)C=CC3C(=O)OCC123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O8/c1-4-13(2)21(27)33-19-9-16-23(29)32-18(14-7-8-30-11-14)10-24(16,3)20-17(26)6-5-15-22(28)31-12-25(15,19)20/h4-8,11,15-16,18-20H,9-10,12H2,1-3H3

> <INCHI_KEY>
SEBUPTPBKYZXJN-UHFFFAOYSA-N

> <FORMULA>
C25H26O8

> <MOLECULAR_WEIGHT>
454.475

> <EXACT_MASS>
454.162767797

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.64107905792114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.036709935666666

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.03532320167196

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.556223212882763

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8877932535453574

> <JCHEM_POLAR_SURFACE_AREA>
109.11000000000001

> <JCHEM_REFRACTIVITY>
115.30369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       7.774   4.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.406   3.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.109   4.798   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.179   6.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.742   4.090   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.444   4.920   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.671   2.552   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.176   1.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.336   2.430   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.633   1.600   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.001   2.308   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.071   3.847   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.298   1.478   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.228  -0.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.860  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.563   0.062   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.493  -1.477   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.196  -0.647   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.125  -2.185   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.423  -3.015   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.758  -2.894   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.461  -2.064   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.531  -0.525   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.435   0.556   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.915   0.305   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.125   1.933   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.647   1.703   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.898   0.183   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.525  -0.890   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.959  -0.328   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.936  -1.519   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.106  -2.816   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.616  -2.427   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    8   18   23                                             
CONECT   29   14   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
7-(Furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0,.0,]heptadec-12-en-2-yl 2-methylbut-2-enoic acid	Generator
7-(Furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₂₆O₈

Average Mass

454.4750 Da

Monoisotopic Mass

454.16277 Da

IUPAC Name

7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate

Traditional Name

7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CC2C(=O)OC(CC2(C)C2C(=O)C=CC3C(=O)OCC123)C1=COC=C1

InChI Identifier

InChI=1S/C25H26O8/c1-4-13(2)21(27)33-19-9-16-23(29)32-18(14-7-8-30-11-14)10-24(16,3)20-17(26)6-5-15-22(28)31-12-25(15,19)20/h4-8,11,15-16,18-20H,9-10,12H2,1-3H3

InChI Key

SEBUPTPBKYZXJN-UHFFFAOYSA-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
Aster verticillatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Fatty acid ester
Cyclohexenone
Delta_valerolactone
Gamma butyrolactone
Fatty acyl
Oxane
Pyran
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	2.64	ALOGPS
logP	3.04	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.3 m³·mol⁻¹	ChemAxon
Polarizability	45.64 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate (NP0200115)

MOL for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

3D MOL for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

3D SDF for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

3D-SDF for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

PDB for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

3D PDB for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

SMILES for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

INCHI for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

Structure for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)

3D Structure for NP0200115 (7-(furan-3-yl)-9-methyl-5,11,15-trioxo-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-en-2-yl 2-methylbut-2-enoate)