NP-MRD: Showing NP-Card for (2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione (NP0149028)

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Record Information

Version

2.0

Created at

2022-09-02 04:51:26 UTC

Updated at

2022-09-02 04:51:26 UTC

NP-MRD ID

NP0149028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione

Description

(2R,12S)-5-hydroxy-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-12-(propan-2-yl)-2,3,4,10,11,12-hexahydro-1,7-dioxatetraphene-4,11-dione belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. (2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione is found in Baeckea frutescens. Based on a literature review very few articles have been published on (2R,12S)-5-hydroxy-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-12-(propan-2-yl)-2,3,4,10,11,12-hexahydro-1,7-dioxatetraphene-4,11-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206512D          

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M  END

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M  END


  Mrv1652309022206512D          

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 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  2  0  0  0  0
 18 36  1  0  0  0  0
  6 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C2=C([C@@H](C(C)C)C3=C(O2)C(C)=C(O)C2=C3O[C@H](CC2=O)C2=CC=CC=C2)C(=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O6/c1-14(2)20-22-25(36-26-16(4)29(34-7)30(5,6)28(33)23(20)26)15(3)24(32)21-18(31)13-19(35-27(21)22)17-11-9-8-10-12-17/h8-12,14,19-20,32H,13H2,1-7H3/t19-,20+/m1/s1

> <INCHI_KEY>
NJQFCQXFOHVYQJ-UXHICEINSA-N

> <FORMULA>
C30H32O6

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.93976089169801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,12S)-5-hydroxy-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-12-(propan-2-yl)-2,3,4,10,11,12-hexahydro-1,7-dioxatetraphene-4,11-dione

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
6.043142481333335

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.841436869583962

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.567029802421407

> <JCHEM_PKA_STRONGEST_BASIC>
-4.50254402931093

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
139.615

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,12S)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2H-1,7-dioxatetraphene-4,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      12.424   0.188   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+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       9.399   3.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+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  O   UNK     0       7.383  -2.140   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.743  -1.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.836  -0.949   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.358   5.427   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   4.844   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.342  -0.394   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -3.304   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.830  -4.760   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.683  -5.051   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.691  -3.887   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.187  -2.431   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.375   3.098   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   36                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   24                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   34                                                  
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   26   34                                                       
CONECT   34   33   23   35                                                  
CONECT   35   34                                                            
CONECT   36   18    6                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₆

Average Mass

488.5800 Da

Monoisotopic Mass

488.21989 Da

IUPAC Name

(2R,12S)-5-hydroxy-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-12-(propan-2-yl)-2,3,4,10,11,12-hexahydro-1,7-dioxatetraphene-4,11-dione

Traditional Name

(2R,12S)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2H-1,7-dioxatetraphene-4,11-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C2=C([C@@H](C(C)C)C3=C(O2)C(C)=C(O)C2=C3O[C@H](CC2=O)C2=CC=CC=C2)C(=O)C1(C)C

InChI Identifier

InChI=1S/C30H32O6/c1-14(2)20-22-25(36-26-16(4)29(34-7)30(5,6)28(33)23(20)26)15(3)24(32)21-18(31)13-19(35-27(21)22)17-11-9-8-10-12-17/h8-12,14,19-20,32H,13H2,1-7H3/t19-,20+/m1/s1

InChI Key

NJQFCQXFOHVYQJ-UXHICEINSA-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
Baeckea frutescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Dibenzopyran
Xanthene
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Vinylogous ester
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	5.38	ALOGPS
logP	6.04	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	139.62 m³·mol⁻¹	ChemAxon
Polarizability	53.94 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

162928235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione (NP0149028)

MOL for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

3D MOL for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

3D SDF for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

3D-SDF for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

PDB for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

3D PDB for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

SMILES for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

INCHI for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

Structure for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)

3D Structure for NP0149028 ((2r,12s)-5-hydroxy-12-isopropyl-9-methoxy-6,8,10,10-tetramethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,11-dione)