NP-MRD: Showing NP-Card for (1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate (NP0260798)

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Record Information

Version

2.0

Created at

2022-09-08 03:03:44 UTC

Updated at

2022-09-08 03:03:44 UTC

NP-MRD ID

NP0260798

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate

Description

(1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]Dodecan-3-yl acetate 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. (1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate is found in Valeriana officinalis. Based on a literature review very few articles have been published on (1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]Dodecan-3-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082205032D          

 24 26  0  0  1  0            999 V2000
    5.4577   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6243    0.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3263    1.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.2489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2167    0.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327    0.2191    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3239   -0.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037    0.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    1.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9646    1.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594    1.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.9561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2622    2.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    1.4935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7431    0.6719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9853    0.3459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8036   -0.4588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -1.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -0.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410    0.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    1.6752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5365    2.4330    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  1  0  0  0
 16 15  1  6  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0260798

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](OC(C)=O)[C@@H]2[C@@H]1C[C@H]1[C@H](C[C@]2(C)OC1(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O5/c1-10-7-15(22-11(2)20)17-13(10)8-14-16(23-12(3)21)9-19(17,6)24-18(14,4)5/h10,13-17H,7-9H2,1-6H3/t10-,13-,14+,15-,16+,17+,19+/m1/s1

> <INCHI_KEY>
UVUBMUALYRCMQK-KJGIFLGISA-N

> <FORMULA>
C19H30O5

> <MOLECULAR_WEIGHT>
338.444

> <EXACT_MASS>
338.209324066

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.16062646023858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

> <JCHEM_LOGP>
1.8319752673333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20858194814517

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
88.23029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.188  -0.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.832   1.216   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.365   1.357   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.942   2.473   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.409   2.331   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.871   0.888   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.408   0.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.205  -1.118   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.540   1.590   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.943   2.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.534   3.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.524   2.072   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.616   3.651   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.090   3.855   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.979   2.788   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.120   1.254   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.706   0.646   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.367  -0.856   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.896  -1.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.557  -2.816   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.765  -0.269   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.690   1.803   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.477   3.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.868   4.542   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   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   16                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15    7   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   15   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3R,5R,6R,8S,12S)-12-(Acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0,]dodecan-3-yl acetic acid	Generator

Chemical Formula

C₁₉H₃₀O₅

Average Mass

338.4440 Da

Monoisotopic Mass

338.20932 Da

IUPAC Name

(1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

Traditional Name

(1S,2S,3R,5R,6R,8S,12S)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](OC(C)=O)[C@@H]2[C@@H]1C[C@H]1[C@H](C[C@]2(C)OC1(C)C)OC(C)=O

InChI Identifier

InChI=1S/C19H30O5/c1-10-7-15(22-11(2)20)17-13(10)8-14-16(23-12(3)21)9-19(17,6)24-18(14,4)5/h10,13-17H,7-9H2,1-6H3/t10-,13-,14+,15-,16+,17+,19+/m1/s1

InChI Key

UVUBMUALYRCMQK-KJGIFLGISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Valeriana officinalis	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

Oxepane
Oxane
Dicarboxylic acid or derivatives
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
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	1.83	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.23 m³·mol⁻¹	ChemAxon
Polarizability	37.16 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	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

88297816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101620273

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,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate (NP0260798)

MOL for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D MOL for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D SDF for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D-SDF for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

PDB for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D PDB for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

SMILES for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

INCHI for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

Structure for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)

3D Structure for NP0260798 ((1s,2s,3r,5r,6r,8s,12s)-12-(acetyloxy)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecan-3-yl acetate)