NP-MRD: Showing NP-Card for (1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate (NP0160003)

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Record Information

Version

2.0

Created at

2022-09-02 17:51:33 UTC

Updated at

2022-09-02 17:51:33 UTC

NP-MRD ID

NP0160003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate

Description

(1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]Heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate is found in Conyza pyrrhopappa. Based on a literature review very few articles have been published on (1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]Heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219512D          

 32 35  0  0  1  0            999 V2000
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   -0.3121   -5.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022219512D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0160003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@H](C[C@@H](C)[C@@H]1C[C@@H](OC1=O)C1=COC=C1)[C@@]1(C)C(=O)CC[C@H]2O[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-6-14(2)22(27)31-21(24(4)19(26)7-8-20-25(24,5)32-20)11-15(3)17-12-18(30-23(17)28)16-9-10-29-13-16/h9-10,13-15,17-18,20-21H,6-8,11-12H2,1-5H3/t14-,15-,17+,18-,20-,21-,24-,25-/m1/s1

> <INCHI_KEY>
BVRLIAHAPALMLE-VQKFQMBVSA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.335470011561966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.507050695666665

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.64664688697228

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869329270610436

> <JCHEM_POLAR_SURFACE_AREA>
95.34

> <JCHEM_REFRACTIVITY>
114.8236

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate

> <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      -2.123  -7.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.583  -7.203   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.187  -8.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.583  -9.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.727  -8.537   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.497  -7.203   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.497  -9.871   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.037  -9.871   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.807  -8.537   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.037  -7.203   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.792  -6.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.807  -5.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.181  -4.463   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.325  -3.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.165  -1.901   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.831  -1.131   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.151   0.376   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.683   0.537   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.309  -0.870   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.659  -4.202   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.339  -5.709   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.369  -6.853   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.807 -11.204   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.360 -11.731   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.987 -10.215   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.720  -8.698   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.434 -10.741   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.702 -12.258   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.522 -13.248   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.342 -14.238   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.075 -12.721   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.558 -12.988   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   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   14   21                                                       
CONECT   21   20   12   22                                                  
CONECT   22   21                                                            
CONECT   23    8   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30   29   23   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R)-1-[(1S,2R,6R)-1,2-Dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₃₄O₇

Average Mass

446.5400 Da

Monoisotopic Mass

446.23045 Da

IUPAC Name

(1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate

Traditional Name

(1R,3R)-1-[(1S,2R,6R)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3S,5R)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@H](C[C@@H](C)[C@@H]1C[C@@H](OC1=O)C1=COC=C1)[C@@]1(C)C(=O)CC[C@H]2O[C@@]12C

InChI Identifier

InChI=1S/C25H34O7/c1-6-14(2)22(27)31-21(24(4)19(26)7-8-20-25(24,5)32-20)11-15(3)17-12-18(30-23(17)28)16-9-10-29-13-16/h9-10,13-15,17-18,20-21H,6-8,11-12H2,1-5H3/t14-,15-,17+,18-,20-,21-,24-,25-/m1/s1

InChI Key

BVRLIAHAPALMLE-VQKFQMBVSA-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
Conyza pyrrhopappa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	3.59	ALOGPS
logP	4.51	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	17.65	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	114.82 m³·mol⁻¹	ChemAxon
Polarizability	47.34 Å³	ChemAxon
Number of Rings	4	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

162971202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate (NP0160003)

MOL for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

3D MOL for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

3D SDF for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

3D-SDF for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

PDB for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

3D PDB for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

SMILES for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

INCHI for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

Structure for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)

3D Structure for NP0160003 ((1r,3r)-1-[(1s,2r,6r)-1,2-dimethyl-3-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-[(3s,5r)-5-(furan-3-yl)-2-oxooxolan-3-yl]butyl (2r)-2-methylbutanoate)