NP-MRD: Showing NP-Card for ((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate (NP0331811)

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Record Information

Version

2.0

Created at

2023-09-13 16:01:08 UTC

Updated at

2024-09-03 04:17:02 UTC

NP-MRD ID

NP0331811

Natural Product DOI

https://doi.org/10.57994/0899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate

Description

((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]Dodecan-4-yl)methyl methanesulfonate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on ((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]Dodecan-4-yl)methyl methanesulfonate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09132316012D          

 23 25  0  0  1  0            999 V2000
   -0.2886   -1.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600   -2.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906   -0.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2045   -0.6355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0154   -0.7874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4027    0.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -0.6606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4281   -1.4715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2062   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330   -2.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -2.9003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8180   -3.6191    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229   -4.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992   -4.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5367   -3.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7905   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656   -1.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -1.4495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1173   -2.2441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009    0.7121    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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21  2  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
  7 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(COS(C)(=O)=O)O[C@@H]1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O4S/c1-11-5-6-14-16(20-14,10-19-21(4,17)18)8-7-13-12(11)9-15(13,2)3/h12-14H,1,5-10H2,2-4H3/t12-,13-,14-,16-/m1/s1

> <INCHI_KEY>
IJTRIZAXBPAFGC-IXYNUQLISA-N

> <FORMULA>
C16H26O4S

> <MOLECULAR_WEIGHT>
314.44

> <EXACT_MASS>
314.155180491

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.45774415559712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4R,6R,10S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl methanesulfonate

> <JCHEM_LOGP>
2.5077821390000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.24388038728339

> <JCHEM_POLAR_SURFACE_AREA>
55.9

> <JCHEM_REFRACTIVITY>
80.50909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4R,6R,10S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl methanesulfonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-23         0                                  
HETATM    1  C   UNK     0      -0.539  -3.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.981  -2.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.232  -4.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.729  -1.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.248  -1.186   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       3.762  -1.470   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       3.032   0.139   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.485   0.651   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.927   0.109   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.682  -1.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.399  -2.747   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.852  -2.235   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.155  -4.088   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.371  -5.414   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       7.127  -6.756   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       7.883  -8.097   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.785  -7.512   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.469  -6.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.209  -3.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.669  -3.708   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.500  -2.706   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       2.086  -4.189   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       2.055   1.329   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   21                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   21                                             
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   12   13   19                                             
CONECT   12   11   10                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   11   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2    5   22                                             
CONECT   22   21                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonic acid	Generator
((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulphonate	Generator
((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulphonic acid	Generator

Chemical Formula

C₁₆H₂₆O₄S

Average Mass

314.4400 Da

Monoisotopic Mass

314.15518 Da

IUPAC Name

[(1R,4R,6R,10S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl methanesulfonate

Traditional Name

[(1R,4R,6R,10S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl methanesulfonate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(COS(C)(=O)=O)O[C@@H]1CCC2=C

InChI Identifier

InChI=1S/C16H26O4S/c1-11-5-6-14-16(20-14,10-19-21(4,17)18)8-7-13-12(11)9-15(13,2)3/h12-14H,1,5-10H2,2-4H3/t12-,13-,14-,16-/m1/s1

InChI Key

IJTRIZAXBPAFGC-IXYNUQLISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C6D6, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C6D6, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C6D6, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C6D6, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.578570142, C₆D₆, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-14	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Caryophyllane sesquiterpenoid
Sesquiterpenoid
Organosulfonic acid ester
Sulfonic acid ester
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Methanesulfonate
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
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	2.51	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.51 m³·mol⁻¹	ChemAxon
Polarizability	34.46 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate (NP0331811)

MOL for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

3D MOL for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

3D SDF for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

3D-SDF for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

PDB for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

3D PDB for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

SMILES for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

INCHI for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

Structure for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)

3D Structure for NP0331811 (((1R,4R,6R,10S)-12,12-Dimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecan-4-yl)methyl methanesulfonate)