NP-MRD: Showing NP-Card for 2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate (NP0303299)

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Record Information

Version

2.0

Created at

2022-09-10 17:32:44 UTC

Updated at

2022-09-10 17:32:44 UTC

NP-MRD ID

NP0303299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate

Description

2,3,13,14,15-Pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]Heptadeca-2,5,11,13,15-pentaen-7-yl acetate belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring. 2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate is found in Kadsura coccinea. 2,3,13,14,15-Pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]Heptadeca-2,5,11,13,15-pentaen-7-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514562D          

 34 37  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004241514562D          

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M  END
> <DATABASE_ID>
NP0303299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=C1)C1OC22C(=CC(=O)C(OC)=C2OC)C(OC(C)=O)C(C)C1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O9/c1-11-12(2)20(33-13(3)26)15-10-16(27)21(29-5)24(32-8)25(15)18-14(19(11)34-25)9-17(28-4)22(30-6)23(18)31-7/h9-12,19-20H,1-8H3

> <INCHI_KEY>
OHOKZEXDBOSOBF-UHFFFAOYSA-N

> <FORMULA>
C25H30O9

> <MOLECULAR_WEIGHT>
474.506

> <EXACT_MASS>
474.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.055405419293756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
1.673662459

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.70650357752475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.986937696394135

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000001

> <JCHEM_REFRACTIVITY>
123.38799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.809   1.893   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.034   0.843   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.702  -0.697   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.002  -1.541   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.281  -0.585   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.000   1.203   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.135  -3.115   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.967  -4.286   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.986  -5.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.997  -6.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.882  -7.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.391  -6.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.933  -8.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.342  -5.401   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.830  -6.009   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.116  -7.406   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.953  -8.699   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.422  -7.484   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.660  -3.830   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.312  -2.972   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.341  -1.422   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.102  -0.759   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.771  -3.734   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.273  -3.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.729  -1.922   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.354  -1.949   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.642  -2.851   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.683  -0.792   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.659   0.556   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.084   1.377   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.181  -1.132   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.162   0.538   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.554   2.175   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.725  -2.603   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   19   34                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
CONECT   23    9   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    7   23                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2,3,13,14,15-Pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0,.0,]heptadeca-2,5,11,13,15-pentaen-7-yl acetic acid	Generator
2,3,13,14,15-Pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₀O₉

Average Mass

474.5060 Da

Monoisotopic Mass

474.18898 Da

IUPAC Name

2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate

Traditional Name

2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C(=C1)C1OC22C(=CC(=O)C(OC)=C2OC)C(OC(C)=O)C(C)C1C

InChI Identifier

InChI=1S/C25H30O9/c1-11-12(2)20(33-13(3)26)15-10-16(27)21(29-5)24(32-8)25(15)18-14(19(11)34-25)9-17(28-4)22(30-6)23(18)31-7/h9-12,19-20H,1-8H3

InChI Key

OHOKZEXDBOSOBF-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
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
Anisole
Alkyl aryl ether
Oxepane
Benzenoid
Vinylogous ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.95	ALOGPS
logP	1.67	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	123.39 m³·mol⁻¹	ChemAxon
Polarizability	48.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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 2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate (NP0303299)

MOL for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

3D MOL for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

3D SDF for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

3D-SDF for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

PDB for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

3D PDB for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

SMILES for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

INCHI for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

Structure for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)

3D Structure for NP0303299 (2,3,13,14,15-pentamethoxy-8,9-dimethyl-4-oxo-17-oxatetracyclo[8.6.1.0¹,⁶.0¹¹,¹⁶]heptadeca-2,5,11,13,15-pentaen-7-yl acetate)