NP-MRD: Showing NP-Card for 5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate (NP0323222)

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Record Information

Version

2.0

Created at

2022-09-12 02:30:35 UTC

Updated at

2022-09-12 02:30:35 UTC

NP-MRD ID

NP0323222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate

Description

5-Hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]Undec-9-en-4-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate is found in Stevia connata. 5-Hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]Undec-9-en-4-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509062D          

 31 33  0  0  0  0            999 V2000
   -3.4643   -1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -2.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -0.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033   -1.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -2.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371   -2.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450   -2.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708   -3.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -3.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420   -3.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3838    0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031    0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968    0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 29  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251509062D          

 31 33  0  0  0  0            999 V2000
   -3.4643   -1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0323222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(OC(=O)C(C)=CC)C(O)C(C)(C)C2C3C(C)=CC(=O)C2C13C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-9-12(3)22(28)30-19-20(27)24(6,7)18-16-14(5)11-15(26)17(18)25(16,8)21(19)31-23(29)13(4)10-2/h9,11,13,16-21,27H,10H2,1-8H3

> <INCHI_KEY>
ZKHHASNAMXUZIT-UHFFFAOYSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.557

> <EXACT_MASS>
432.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.82892786631399

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
4.655095403666666

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.36325600184357

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.651437175224114

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3885663847391374

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
117.20659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -6.467  -2.944   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.133  -2.174   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.799  -2.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.799  -4.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.466  -2.174   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.466  -0.634   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.132  -2.944   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.202  -2.174   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.686  -2.802   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.710  -4.342   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.056  -5.091   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.377  -4.301   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.080  -6.631   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.426  -7.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -6.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.758  -7.422   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.125  -2.140   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.307  -3.127   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.526  -0.579   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.914  -1.245   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.450   0.654   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.432   0.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.990   1.075   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.554   0.699   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.673  -0.872   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.849  -1.551   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.959  -3.087   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.055  -0.791   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.422  -0.399   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.032   0.110   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.728   1.696   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   28                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29                                                  
CONECT   29   28    8   23   30                                             
CONECT   30   29                                                            
CONECT   31   24                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0,]undec-9-en-4-yl 2-methylbut-2-enoic acid	Generator
5-Hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5570 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate

Traditional Name

5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(OC(=O)C(C)=CC)C(O)C(C)(C)C2C3C(C)=CC(=O)C2C13C

InChI Identifier

InChI=1S/C25H36O6/c1-9-12(3)22(28)30-19-20(27)24(6,7)18-16-14(5)11-15(26)17(18)25(16,8)21(19)31-23(29)13(4)10-2/h9,11,13,16-21,27H,10H2,1-8H3

InChI Key

ZKHHASNAMXUZIT-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
Stevia connata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Cyclohexenone
Fatty acid ester
Cyclitol or derivatives
Fatty acyl
Dicarboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.84	ALOGPS
logP	4.66	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.21 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

73817321

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-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate (NP0323222)

MOL for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

3D MOL for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

3D SDF for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

3D-SDF for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

PDB for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

3D PDB for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

SMILES for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

INCHI for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

Structure for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)

3D Structure for NP0323222 (5-hydroxy-2,6,6,9-tetramethyl-3-[(2-methylbutanoyl)oxy]-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-4-yl 2-methylbut-2-enoate)