NP-MRD: Showing NP-Card for (15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione (NP0236503)

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Record Information

Version

2.0

Created at

2022-09-06 19:25:18 UTC

Updated at

2022-09-06 19:25:18 UTC

NP-MRD ID

NP0236503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione

Description

(15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]Heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione belongs to the class of organic compounds known as coumarino-alpha-pyrones. These are organic compounds with a structure characterized by the presence of a pyrano[3,2-c]chromene that carries two ketone groups at the 2- and 5-positions. (15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione is found in Lysimachia fordiana. Based on a literature review very few articles have been published on (15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]Heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062221252D          

 33 36  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309062221252D          

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M  END
> <DATABASE_ID>
NP0236503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1=CC2=C(OC1=O)C1=C3C[C@@H](CCCCC)OC3=C(OC)C=C1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O6/c1-4-6-8-9-11-12-17-14-20-25(33-26(17)28)23-19-15-18(13-10-7-5-2)31-24(19)22(30-3)16-21(23)32-27(20)29/h14,16,18H,4-13,15H2,1-3H3/t18-/m1/s1

> <INCHI_KEY>
JWDWHWWHBHVHBZ-GOSISDBHSA-N

> <FORMULA>
C27H34O6

> <MOLECULAR_WEIGHT>
454.563

> <EXACT_MASS>
454.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.86824416898899

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione

> <JCHEM_LOGP>
6.186566139666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.61565932551247

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
127.21139999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.006  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      25.340  -3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.674  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.674  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.007  -8.470   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.007 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.340  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.006  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.006  -6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      21.339  -6.160   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.672  -6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.862  -8.730   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.488 -10.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.718 -11.471   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.178 -11.471   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.408 -12.805   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.178 -14.138   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.718 -14.138   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      25.020  -9.976   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   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   33                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   14   22                                                  
CONECT   22   21   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24                                                            
CONECT   26   20   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   27   19                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₆

Average Mass

454.5630 Da

Monoisotopic Mass

454.23554 Da

IUPAC Name

(15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione

Traditional Name

(15R)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),5,10,12-pentaene-4,8-dione

CAS Registry Number

Not Available

SMILES

CCCCCCCC1=CC2=C(OC1=O)C1=C3C[C@@H](CCCCC)OC3=C(OC)C=C1OC2=O

InChI Identifier

InChI=1S/C27H34O6/c1-4-6-8-9-11-12-17-14-20-25(33-26(17)28)23-19-15-18(13-10-7-5-2)31-24(19)22(30-3)16-21(23)32-27(20)29/h14,16,18H,4-13,15H2,1-3H3/t18-/m1/s1

InChI Key

JWDWHWWHBHVHBZ-GOSISDBHSA-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
Lysimachia fordiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarino-alpha-pyrones. These are organic compounds with a structure characterized by the presence of a pyrano[3,2-c]chromene that carries two ketone groups at the 2- and 5-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarino-alpha-pyrones

Direct Parent

Coumarino-alpha-pyrones

Alternative Parents

Substituents

Coumarino-alpha-pyrone
Angular furanocoumarin
Furanocoumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	6.19	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	127.21 m³·mol⁻¹	ChemAxon
Polarizability	52.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162946201

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione (NP0236503)

MOL for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

3D MOL for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

3D SDF for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

3D-SDF for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

PDB for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

3D PDB for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

SMILES for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

INCHI for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

Structure for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)

3D Structure for NP0236503 ((15r)-5-heptyl-12-methoxy-15-pentyl-3,9,14-trioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),5,11,13(17)-pentaene-4,8-dione)