NP-MRD: Showing NP-Card for 14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one (NP0168442)

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Record Information

Version

2.0

Created at

2022-09-03 04:15:26 UTC

Updated at

2022-09-03 04:15:26 UTC

NP-MRD ID

NP0168442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one

Description

14-Ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]Tetradecan-5-one belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. 14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one is found in Hymenoxys hoopesii, Hymenoxys richardsonii and Psilostrophe cooperi. 14-Ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]Tetradecan-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161523372D          

 22 24  0  0  0  0            999 V2000
    1.1189   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443   -3.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553   -2.7318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807   -1.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -1.6735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206   -0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650   -0.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172   -0.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933   -0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6112   -1.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1817   -1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2464   -2.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782   -1.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -1.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056   -2.1882    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1OC(O)CC2C(C)CC3OC(=O)C(=C)C3CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O5/c1-5-20-16-17(4)8-11-10(3)15(19)21-13(11)6-9(2)12(17)7-14(18)22-16/h9,11-14,16,18H,3,5-8H2,1-2,4H3

> <INCHI_KEY>
UIFSGDQXHQSWGC-UHFFFAOYSA-N

> <FORMULA>
C17H26O5

> <MOLECULAR_WEIGHT>
310.39

> <EXACT_MASS>
310.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.94519342124423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
2.6563859436666677

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.398967732929947

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9364915136164393

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.0854

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.089  -7.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.763  -6.134   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.903  -5.099   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.577  -3.594   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.111  -3.124   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.785  -1.619   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.681  -1.148   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.926  -0.584   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.392  -1.054   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.366   0.139   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.713   1.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.906   0.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.852  -1.093   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.387  -0.972   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.977  -2.395   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.474  -2.754   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.806  -3.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.927  -4.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.493  -2.590   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.098  -3.243   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.718  -2.559   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.930  -4.085   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4    9   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₅

Average Mass

310.3900 Da

Monoisotopic Mass

310.17802 Da

IUPAC Name

14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one

Traditional Name

14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one

CAS Registry Number

Not Available

SMILES

CCOC1OC(O)CC2C(C)CC3OC(=O)C(=C)C3CC12C

InChI Identifier

InChI=1S/C17H26O5/c1-5-20-16-17(4)8-11-10(3)15(19)21-13(11)6-9(2)12(17)7-14(18)22-16/h9,11-14,16,18H,3,5-8H2,1-2,4H3

InChI Key

UIFSGDQXHQSWGC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dugaldia hoopesii	LOTUS Database	35616633
Hymenoxys richardsonii	LOTUS Database	35616633
Psilostrophe cooperi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Gamma butyrolactone
Oxane
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Hemiacetal
Lactone
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	1.23	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.4	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.09 m³·mol⁻¹	ChemAxon
Polarizability	33.95 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

282785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one (NP0168442)

MOL for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

3D MOL for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

3D SDF for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

3D-SDF for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

PDB for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

3D PDB for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

SMILES for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

INCHI for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

Structure for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)

3D Structure for NP0168442 (14-ethoxy-12-hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0³,⁷]tetradecan-5-one)