NP-MRD: Showing NP-Card for (2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione (NP0315445)

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Record Information

Version

2.0

Created at

2022-09-11 14:04:57 UTC

Updated at

2022-09-11 14:04:58 UTC

NP-MRD ID

NP0315445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione

Description

Ericifolione belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione is found in Kunzea ericifolia. (2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione was first documented in 2021 (PMID: 34878459). Based on a literature review very few articles have been published on ericifolione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216042D          

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M  END


  Mrv1652309112216042D          

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    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  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  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  7 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
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0315445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H]1[C@H](C(C)C)[C@@H](OC2=C1C(=O)C(C)(C)C(=O)C2(C)C)C1=C(O)C(C)(C)C(=O)C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O6/c1-14(2)13-16-17(15(3)4)20(19-22(32)28(7,8)25(34)29(9,10)23(19)33)36-24-18(16)21(31)27(5,6)26(35)30(24,11)12/h14-17,20,32H,13H2,1-12H3/t16-,17-,20+/m0/s1

> <INCHI_KEY>
VXGYLHHZNVRJQJ-ABSDTBQOSA-N

> <FORMULA>
C30H44O6

> <MOLECULAR_WEIGHT>
500.676

> <EXACT_MASS>
500.313789137

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.93250858765172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3-(propan-2-yl)-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-5,7-dione

> <JCHEM_LOGP>
7.424050551666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.495342017999555

> <JCHEM_PKA_STRONGEST_BASIC>
-4.86158975939759

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
141.5932

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2H-1-benzopyran-5,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.861  -1.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.851   0.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.991   3.490   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.011   3.490   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.573  -4.326   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.199  -3.241   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.518  -2.043   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.528  -3.757   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   10   22                                                  
CONECT   22   21                                                            
CONECT   23    9    5   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    7   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    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₆

Average Mass

500.6760 Da

Monoisotopic Mass

500.31379 Da

IUPAC Name

(2R,3S,4S)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3-(propan-2-yl)-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-5,7-dione

Traditional Name

(2R,3S,4S)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2H-1-benzopyran-5,7-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H]1[C@H](C(C)C)[C@@H](OC2=C1C(=O)C(C)(C)C(=O)C2(C)C)C1=C(O)C(C)(C)C(=O)C(C)(C)C1=O

InChI Identifier

InChI=1S/C30H44O6/c1-14(2)13-16-17(15(3)4)20(19-22(32)28(7,8)25(34)29(9,10)23(19)33)36-24-18(16)21(31)27(5,6)26(35)30(24,11)12/h14-17,20,32H,13H2,1-12H3/t16-,17-,20+/m0/s1

InChI Key

VXGYLHHZNVRJQJ-ABSDTBQOSA-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
Kunzea ericifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Secoiridoid-skeleton
Benzopyran
Bicyclic monoterpenoid
M-benzoquinone
Quinone
Cyclohexenone
Vinylogous ester
Vinylogous acid
Ketone
Cyclic ketone
Enol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	7.42	ChemAxon
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.59 m³·mol⁻¹	ChemAxon
Polarizability	55.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

8990559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10815254

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou T, Zheng A, Huo L, Li C, Tan H, Wang S, Chen H: Total syntheses of ericifolione and its analogues via a biomimetic inverse-electron-demand Diels-Alder reaction. Chem Commun (Camb). 2021 Dec 23;58(2):270-273. doi: 10.1039/d1cc06361h. [PubMed:34878459 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione (NP0315445)

MOL for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

3D MOL for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

3D SDF for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

3D-SDF for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

PDB for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

3D PDB for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

SMILES for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

INCHI for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

Structure for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)

3D Structure for NP0315445 ((2r,3s,4s)-2-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-isopropyl-6,6,8,8-tetramethyl-4-(2-methylpropyl)-3,4-dihydro-2h-1-benzopyran-5,7-dione)