NP-MRD: Showing NP-Card for 7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione (NP0254776)

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Record Information

Version

2.0

Created at

2022-09-07 19:02:48 UTC

Updated at

2022-09-07 19:02:49 UTC

NP-MRD ID

NP0254776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione

Description

Territrem B 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. Territrem B is an extremely weak basic (essentially neutral) compound (based on its pKa). Territrem B is a potentially toxic compound. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. The biotransformation of territrems involves hydroxylation and 0-demethylation. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212482D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241212482D          

 38 42  0  0  0  0            999 V2000
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  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 34  1  0  0  0  0
 11 35  1  0  0  0  0
  8 36  1  0  0  0  0
  7 37  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1=CC2=C(CC3(O)C(C)(CCC4(O)C(C)(C)C=CC(=O)C34C)O2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O9/c1-25(2)9-8-22(30)27(4)28(25,32)11-10-26(3)29(27,33)15-17-19(38-26)14-18(37-24(17)31)16-12-20(34-5)23(36-7)21(13-16)35-6/h8-9,12-14,32-33H,10-11,15H2,1-7H3

> <INCHI_KEY>
PBXNNDFKPQPJBB-UHFFFAOYSA-N

> <FORMULA>
C29H34O9

> <MOLECULAR_WEIGHT>
526.5749

> <EXACT_MASS>
526.220282686

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
55.910635967965916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.5050752239999983

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.756136782456121

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.496045503460596

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3658431139009384

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000001

> <JCHEM_REFRACTIVITY>
140.3431

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       9.423  -1.934   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.374   3.098   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.350  -1.558   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.326   1.934   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.342   3.680   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.691   0.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.195  -1.267   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.707  -1.558   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.715  -0.394   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.211   1.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.699   1.352   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.219   2.225   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.715   3.680   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.228  -0.685   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.732  -2.140   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.211  -3.013   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.724  -3.304   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.870   1.643   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.358  -2.722   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.895  -1.849   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.747   2.013   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.920  -0.638   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   38                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   37                                             
CONECT    8    7    2    9   36                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   35                                             
CONECT   12   11    7   13   34                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30                                                            
CONECT   32   24   33                                                       
CONECT   33   32                                                            
CONECT   34   12                                                            
CONECT   35   11                                                            
CONECT   36    8                                                            
CONECT   37    7                                                            
CONECT   38    2                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₉

Average Mass

526.5749 Da

Monoisotopic Mass

526.22028 Da

IUPAC Name

7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

Traditional Name

7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1=CC2=C(CC3(O)C(C)(CCC4(O)C(C)(C)C=CC(=O)C34C)O2)C(=O)O1

InChI Identifier

InChI=1S/C29H34O9/c1-25(2)9-8-22(30)27(4)28(25,32)11-10-26(3)29(27,33)15-17-19(38-26)14-18(37-24(17)31)16-12-20(34-5)23(36-7)21(13-16)35-6/h8-9,12-14,32-33H,10-11,15H2,1-7H3

InChI Key

PBXNNDFKPQPJBB-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
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Cyclohexenone
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous ester
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Lactone
Ketone
Ether
Oxacycle
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.93	ALOGPS
logP	2.51	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.5	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.34 m³·mol⁻¹	ChemAxon
Polarizability	55.91 Å³	ChemAxon
Number of Rings	5	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

5255814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione (NP0254776)

MOL for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

3D MOL for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

3D SDF for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

3D-SDF for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

PDB for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

3D PDB for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

SMILES for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

INCHI for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

Structure for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)

3D Structure for NP0254776 (7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-3-(3,4,5-trimethoxyphenyl)-7,12-dihydro-6h-2,5-dioxatetraphene-1,11-dione)