NP-MRD: Showing NP-Card for 2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione (NP0234076)

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Record Information

Version

2.0

Created at

2022-09-06 15:55:01 UTC

Updated at

2022-09-06 15:55:02 UTC

NP-MRD ID

NP0234076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione

Description

2,14-Dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]Icosa-4(9),7-diene-5,19-dione 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. Based on a literature review very few articles have been published on 2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]Icosa-4(9),7-diene-5,19-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217552D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062217552D          

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    7.9725    0.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7798    0.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3306    0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1380    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0363   -0.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8436   -0.7548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3944   -0.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 16 32  1  0  0  0  0
  8 32  1  0  0  0  0
  5 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1=CC2=C(CC3(O)C(C)(CCC4(O)C(C)(C)C5CC(=O)C34CO5)O2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O10/c1-25(2)22-12-21(30)27(14-37-22)28(25,32)8-7-26(3)29(27,33)13-16-18(39-26)11-17(38-24(16)31)15-9-19(34-4)23(36-6)20(10-15)35-5/h9-11,22,32-33H,7-8,12-14H2,1-6H3

> <INCHI_KEY>
ATLGSZPVKAPATP-UHFFFAOYSA-N

> <FORMULA>
C29H34O10

> <MOLECULAR_WEIGHT>
542.581

> <EXACT_MASS>
542.215197295

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.85191478253252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0^{1,14}.0^{2,11}.0^{4,9}]icosa-4(9),7-diene-5,19-dione

> <JCHEM_LOGP>
1.3132805429999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.789528487968848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.819476152470983

> <JCHEM_PKA_STRONGEST_BASIC>
-3.401757332893901

> <JCHEM_POLAR_SURFACE_AREA>
129.98000000000002

> <JCHEM_REFRACTIVITY>
138.87589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0^{1,14}.0^{2,11}.0^{4,9}]icosa-4(9),7-diene-5,19-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      17.825  -4.019   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.318  -3.702   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.840  -2.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.333  -1.921   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.854  -0.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.347  -0.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.319  -1.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.812  -0.969   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.333   0.494   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.361   1.641   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.882   3.105   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.868   1.324   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.826   0.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.798  -0.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.502   1.176   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.276  -1.799   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.723  -3.272   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.165  -2.933   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.665  -2.416   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.178  -0.900   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.635   0.541   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.461  -0.719   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.578  -2.255   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.972  -1.112   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.714   0.867   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.935   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.655   2.012   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.540   3.273   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.351   0.369   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.117   1.063   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.948   0.383   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.783  -2.116   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.882   0.689   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.389   0.372   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.417   1.518   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      18.924   1.201   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.868  -1.092   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      18.375  -1.409   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      19.403  -0.263   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15   16   29                                             
CONECT   15   14                                                            
CONECT   16   14   17   18   32                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   29                                             
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   20   30                                             
CONECT   30   29   31                                                       
CONECT   31   30   25                                                       
CONECT   32   16    8                                                       
CONECT   33    5   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34    3   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₀

Average Mass

542.5810 Da

Monoisotopic Mass

542.21520 Da

IUPAC Name

2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0^{1,14}.0^{2,11}.0^{4,9}]icosa-4(9),7-diene-5,19-dione

Traditional Name

2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0^{1,14}.0^{2,11}.0^{4,9}]icosa-4(9),7-diene-5,19-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1=CC2=C(CC3(O)C(C)(CCC4(O)C(C)(C)C5CC(=O)C34CO5)O2)C(=O)O1

InChI Identifier

InChI=1S/C29H34O10/c1-25(2)22-12-21(30)27(14-37-22)28(25,32)8-7-26(3)29(27,33)13-16-18(39-26)11-17(38-24(16)31)15-9-19(34-4)23(36-6)20(10-15)35-5/h9-11,22,32-33H,7-8,12-14H2,1-6H3

InChI Key

ATLGSZPVKAPATP-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

Not Available

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
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Tertiary alcohol
Cyclic alcohol
Lactone
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.31	ChemAxon
pKa (Strongest Acidic)	12.82	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	129.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.88 m³·mol⁻¹	ChemAxon
Polarizability	56.85 Å³	ChemAxon
Number of Rings	6	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

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

162959725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione (NP0234076)

MOL for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

3D MOL for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

3D SDF for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

3D-SDF for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

PDB for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

3D PDB for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

SMILES for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

INCHI for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

Structure for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)

3D Structure for NP0234076 (2,14-dihydroxy-11,15,15-trimethyl-7-(3,4,5-trimethoxyphenyl)-6,10,17-trioxapentacyclo[14.2.2.0¹,¹⁴.0²,¹¹.0⁴,⁹]icosa-4(9),7-diene-5,19-dione)