NP-MRD: Showing NP-Card for (1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol (NP0224447)

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Record Information

Version

2.0

Created at

2022-09-06 02:48:23 UTC

Updated at

2022-09-06 02:48:23 UTC

NP-MRD ID

NP0224447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol

Description

(1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]Heptadeca-3,13(16)-dien-5-ol belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Based on a literature review very few articles have been published on (1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]Heptadeca-3,13(16)-dien-5-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204482D          

 26 28  0  0  1  0            999 V2000
    6.2848    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5071    1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575    0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -0.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2525    0.1746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5865   -0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021    0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4045    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    2.0723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9055    2.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957    3.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014    2.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791    2.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295    1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    2.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841    2.5931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6115    3.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    1.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    2.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741    1.3239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2903    1.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1652309062204482D          

 26 28  0  0  1  0            999 V2000
    6.2848    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5071    1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575    0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -0.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2525    0.1746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5865   -0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021    0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4045    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9076    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    2.0723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9055    2.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957    3.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014    2.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791    2.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295    1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    2.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841    2.5931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6115    3.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    1.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    2.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741    1.3239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2903    1.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@]2(C\C(C)=C\[C@H](O)CC(=C)CC[C@H]3CCC1=C2C3(C)C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-14-7-8-16-9-10-18-19(21(16,3)4)22(25-6,26-20(18)24-5)13-15(2)12-17(23)11-14/h12,16-17,20,23H,1,7-11,13H2,2-6H3/b15-12+/t16-,17+,20-,22-/m0/s1

> <INCHI_KEY>
XFWZSUKBNFVIMQ-YURZRUJYSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.1174297373455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-5-ol

> <JCHEM_LOGP>
4.058319681666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.227681843985074

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3857532272041535

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
104.39399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      11.732   1.812   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.280   2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.390  -0.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.938   0.326   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.695  -0.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.286   0.039   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.120   1.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.206   2.354   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.657   1.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.222   3.273   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.161   2.173   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.925   3.868   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.424   5.324   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.912   5.618   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.096   4.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.548   4.354   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.828   2.840   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.719   5.355   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.170   4.841   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.341   5.841   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.451   3.326   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.343   3.937   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.872   2.471   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.409   1.991   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.261   3.018   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   16   23                                             
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2                                                       
CONECT   23   13   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-5-ol

Traditional Name

(1S,3E,5R,10S,14S)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-5-ol

CAS Registry Number

Not Available

SMILES

CO[C@H]1O[C@]2(C\C(C)=C\[C@H](O)CC(=C)CC[C@H]3CCC1=C2C3(C)C)OC

InChI Identifier

InChI=1S/C22H34O4/c1-14-7-8-16-9-10-18-19(21(16,3)4)22(25-6,26-20(18)24-5)13-15(2)12-17(23)11-14/h12,16-17,20,23H,1,7-11,13H2,2-6H3/b15-12+/t16-,17+,20-,22-/m0/s1

InChI Key

XFWZSUKBNFVIMQ-YURZRUJYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Dihydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
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	4.06	ChemAxon
pKa (Strongest Acidic)	18.23	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.39 m³·mol⁻¹	ChemAxon
Polarizability	41.12 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

163018465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol (NP0224447)

MOL for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

3D MOL for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

3D SDF for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

3D-SDF for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

PDB for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

3D PDB for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

SMILES for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

INCHI for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

Structure for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)

3D Structure for NP0224447 ((1s,3e,5r,10s,14s)-1,14-dimethoxy-3,17,17-trimethyl-7-methylidene-15-oxatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-5-ol)