NP-MRD: Showing NP-Card for 5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione (NP0250559)

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Record Information

Version

2.0

Created at

2022-09-07 13:24:39 UTC

Updated at

2022-09-07 13:24:39 UTC

NP-MRD ID

NP0250559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione

Description

5-Hydroxy-6,8,8,10,10-pentamethyl-2-phenyl-12-(propan-2-yl)-2,3,4,8,9,10,11,12-octahydro-1,7-dioxatetraphene-4,9,11-trione 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. 5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione is found in Luma chequen. 5-Hydroxy-6,8,8,10,10-pentamethyl-2-phenyl-12-(propan-2-yl)-2,3,4,8,9,10,11,12-octahydro-1,7-dioxatetraphene-4,9,11-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503592D          

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  Mrv1533004161503592D          

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 21 26  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0250559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1C2=C(OC3=C(C)C(O)=C4C(=O)CC(OC4=C13)C1=CC=CC=C1)C(C)(C)C(=O)C(C)(C)C2=O

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

> <INCHI_KEY>
OPEYJCQUCFYYHO-UHFFFAOYSA-N

> <FORMULA>
C30H32O6

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.46147513512202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-6,8,8,10,10-pentamethyl-2-phenyl-12-(propan-2-yl)-2,3,4,8,9,10,11,12-octahydro-1,7-dioxatetraphene-4,9,11-trione

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
7.151439595

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.846213024766715

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.572248479174585

> <JCHEM_PKA_STRONGEST_BASIC>
-4.805110659662912

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
137.3416

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2H-1,7-dioxatetraphene-4,9,11-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      13.043  -3.868   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.531  -3.577   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.522  -4.741   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.018   0.788   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.035   3.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.059   2.534   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.076   0.788   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.051  -2.704   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.067  -4.450   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.580  -4.741   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.084  -6.197   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.076  -7.361   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.563  -7.070   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.059  -5.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.047   1.354   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.176   0.706   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.978  -0.958   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.473  -2.948   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.970  -4.244   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.010  -4.450   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6   35                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19    4    8                                                  
CONECT   21   17   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    6   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    5   36                                                  
CONECT   36   35                                                            
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

5-hydroxy-6,8,8,10,10-pentamethyl-2-phenyl-12-(propan-2-yl)-2,3,4,8,9,10,11,12-octahydro-1,7-dioxatetraphene-4,9,11-trione

Traditional Name

5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2H-1,7-dioxatetraphene-4,9,11-trione

CAS Registry Number

Not Available

SMILES

CC(C)C1C2=C(OC3=C(C)C(O)=C4C(=O)CC(OC4=C13)C1=CC=CC=C1)C(C)(C)C(=O)C(C)(C)C2=O

InChI Identifier

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

InChI Key

OPEYJCQUCFYYHO-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
Luma chequen	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
Alkyl aryl ether
Phenol
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Vinylogous ester
Cyclic ketone
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.46	ALOGPS
logP	7.15	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.34 m³·mol⁻¹	ChemAxon
Polarizability	53.46 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

85376106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione (NP0250559)

MOL for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

3D MOL for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

3D SDF for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

3D-SDF for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

PDB for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

3D PDB for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

SMILES for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

INCHI for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

Structure for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)

3D Structure for NP0250559 (5-hydroxy-12-isopropyl-6,8,8,10,10-pentamethyl-2-phenyl-3,12-dihydro-2h-1,7-dioxatetraphene-4,9,11-trione)