NP-MRD: Showing NP-Card for (1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate (NP0256355)

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Record Information

Version

1.0

Created at

2022-09-07 21:09:16 UTC

Updated at

2022-09-07 21:09:16 UTC

NP-MRD ID

NP0256355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate

Description

[(1S,2S,3'aR,5R,7'aR)-1,3'a-dimethyl-3-oxo-1',3',3'a,7'a-tetrahydro-4,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-indene]-7'-yl]methyl acetate belongs to the class of organic compounds known as enol ester epoxides. These are epoxide containing derivatives of enol esters. They have an acyloxy substituent on either carbon atom of the epoxide ring and their general structure is CC1OC1OC(R)=O, R = H or organyl chain. (1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate is found in Tubipora musica. Based on a literature review very few articles have been published on [(1S,2S,3'aR,5R,7'aR)-1,3'a-dimethyl-3-oxo-1',3',3'a,7'a-tetrahydro-4,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-indene]-7'-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223092D          

 22 25  0  0  1  0            999 V2000
    7.2313    3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6442    2.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8487    2.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527    1.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    1.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4741    0.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2696    0.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4781   -0.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8911   -1.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955   -0.9336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2194   -1.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4008   -1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -0.8553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0635   -0.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8871   -0.1354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4624   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074   -2.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389   -1.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304   -0.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3924    0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.3321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5788    0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
  6 15  1  0  0  0  0
 10 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
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0256355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=CC=C[C@@]2(C)C[C@]3(C[C@@H]12)C(=O)O[C@H]1O[C@@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-10(18)20-8-11-5-4-6-15(2)9-17(7-12(11)15)13(19)21-14-16(17,3)22-14/h4-6,12,14H,7-9H2,1-3H3/t12-,14-,15-,16+,17+/m0/s1

> <INCHI_KEY>
BDSXZZAVGRHBQR-ZZTPXLKCSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.906613895922252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2S,3'aR,5R,7'aR)-1,7'a-dimethyl-3-oxo-1',3',3'a,7'a-tetrahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-4'-yl]methyl acetate

> <JCHEM_LOGP>
1.8123924173333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4245112213346305

> <JCHEM_POLAR_SURFACE_AREA>
65.13000000000001

> <JCHEM_REFRACTIVITY>
78.5624

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3'aR,5R,7'aR)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'H-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-4'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      13.498   5.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.403   4.891   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.918   5.299   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.792   3.401   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.696   2.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.085   0.829   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.570   0.421   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.959  -1.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.863  -2.151   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.378  -1.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.610  -3.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.081  -2.573   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.891  -1.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.452  -0.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.989  -0.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.330  -3.031   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.160  -4.328   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.793  -2.940   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.403  -1.450   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.333   0.088   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.700  -0.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.547   0.666   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   16   21                                             
CONECT   14   13   15                                                       
CONECT   15   14    6   10                                                  
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   13   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2S,3'AR,5R,7'ar)-1,3'a-dimethyl-3-oxo-1',3',3'a,7'a-tetrahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-7'-yl]methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

[(1S,2S,3'aR,5R,7'aR)-1,7'a-dimethyl-3-oxo-1',3',3'a,7'a-tetrahydro-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-4'-yl]methyl acetate

Traditional Name

(1S,2S,3'aR,5R,7'aR)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'H-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-4'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=CC=C[C@@]2(C)C[C@]3(C[C@@H]12)C(=O)O[C@H]1O[C@@]31C

InChI Identifier

InChI=1S/C17H20O5/c1-10(18)20-8-11-5-4-6-15(2)9-17(7-12(11)15)13(19)21-14-16(17,3)22-14/h4-6,12,14H,7-9H2,1-3H3/t12-,14-,15-,16+,17+/m0/s1

InChI Key

BDSXZZAVGRHBQR-ZZTPXLKCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tubipora musica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enol ester epoxides. These are epoxide containing derivatives of enol esters. They have an acyloxy substituent on either carbon atom of the epoxide ring and their general structure is CC1OC1OC(R)=O, R = H or organyl chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Enol ester epoxides

Direct Parent

Enol ester epoxides

Alternative Parents

Substituents

Enol ester epoxide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Meta-dioxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.81	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.56 m³·mol⁻¹	ChemAxon
Polarizability	30.91 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	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

10472532

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23426587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate (NP0256355)

MOL for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

3D MOL for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

3D SDF for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

3D-SDF for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

PDB for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

3D PDB for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

SMILES for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

INCHI for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

Structure for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)

3D Structure for NP0256355 ((1s,2s,3'ar,5r,7'ar)-1,7'a-dimethyl-3-oxo-3',3'a-dihydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-4'-ylmethyl acetate)