NP-MRD: Showing NP-Card for 5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate (NP0215811)

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Record Information

Version

2.0

Created at

2022-09-05 15:33:17 UTC

Updated at

2022-09-05 15:33:17 UTC

NP-MRD ID

NP0215811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate

Description

5-(Acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl 3-phenyloxirane-2-carboxylate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). 5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate is found in Celastrus gemmatus. 5-(Acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl 3-phenyloxirane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171502592D          

 32 36  0  0  0  0            999 V2000
    2.6419    2.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588    1.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7894    1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332    0.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0079   -0.7014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298   -0.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1786   -1.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -0.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281    0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2176   -0.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    0.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    0.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154    0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    1.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575    1.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    1.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8164   -1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960   -2.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711   -2.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -3.2117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916   -3.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3713   -4.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -5.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5463   -4.3171    0.0000 C   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
  3  4  1  0  0  0  0
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  5  6  1  0  0  0  0
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  5 10  1  0  0  0  0
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  2 16  1  0  0  0  0
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 27 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004171502592D          

 32 36  0  0  0  0            999 V2000
    2.6419    2.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588    1.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5711   -2.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0215811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(OC(C)=O)C2(C)C(CC3CC12OC3(C)C)OC(=O)C1OC1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-15-11-12-19(29-16(2)27)25(5)20(13-18-14-26(15,25)32-24(18,3)4)30-23(28)22-21(31-22)17-9-7-6-8-10-17/h6-10,15,18-22H,11-14H2,1-5H3

> <INCHI_KEY>
UVQBFVAQOIQSEE-UHFFFAOYSA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.552

> <EXACT_MASS>
442.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.79374471993279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.030909942333331

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.959135461682718

> <JCHEM_POLAR_SURFACE_AREA>
74.36

> <JCHEM_REFRACTIVITY>
116.37150000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.932   4.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.523   2.905   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.074   2.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.715   1.354   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.830   0.086   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.481  -1.309   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.016  -1.443   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.667  -2.839   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.899  -0.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.279   0.223   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.006  -1.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.502  -1.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.907  -1.128   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.148   0.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.379   0.935   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.509   1.678   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.188   2.714   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.787   1.878   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.851   3.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.257   1.709   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.257  -2.543   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.473  -3.868   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.933  -3.852   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.228  -5.211   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.553  -5.995   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.211  -6.750   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.426  -8.076   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.182  -9.418   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.397 -10.743   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.857 -10.726   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.102  -9.384   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.886  -8.059   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   10   17                                             
CONECT   17   16   18                                                       
CONECT   18   17   14   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25   24   27                                                  
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                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-7-yl 3-phenyloxirane-2-carboxylic acid	Generator
5-(Acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5520 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate

Traditional Name

5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1CCC(OC(C)=O)C2(C)C(CC3CC12OC3(C)C)OC(=O)C1OC1C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H34O6/c1-15-11-12-19(29-16(2)27)25(5)20(13-18-14-26(15,25)32-24(18,3)4)30-23(28)22-21(31-22)17-9-7-6-8-10-17/h6-10,15,18-22H,11-14H2,1-5H3

InChI Key

UVQBFVAQOIQSEE-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
Celastrus gemmatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Oxepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Oxirane carboxylic acid
Benzenoid
Oxirane carboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	4.64	ALOGPS
logP	4.03	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.37 m³·mol⁻¹	ChemAxon
Polarizability	47.79 Å³	ChemAxon
Number of Rings	5	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

14757794

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate (NP0215811)

MOL for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

3D MOL for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

3D SDF for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

3D-SDF for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

PDB for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

3D PDB for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

SMILES for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

INCHI for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

Structure for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)

3D Structure for NP0215811 (5-(acetyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl 3-phenyloxirane-2-carboxylate)