NP-MRD: Showing NP-Card for {9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate (NP0224260)

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Record Information

Version

2.0

Created at

2022-09-06 02:34:47 UTC

Updated at

2022-09-06 02:34:47 UTC

NP-MRD ID

NP0224260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate

Description

{9-Methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. {9-Methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121518292D          

 22 24  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044   -1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9594   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -2.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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  2  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC=C(COC(C)=O)C2=C(C)C2=C(C)C=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c1-10-6-5-7-14-15(10)11(2)16-13(8-21-12(3)19)9-22-18(16)17(14)20-4/h5-7,9H,8H2,1-4H3

> <INCHI_KEY>
QZKFLEVSBJRTEL-UHFFFAOYSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.53712383438825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
3.664793129333333

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.932015176237389

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
83.86230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.782  -2.261   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.257  -3.725   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.764  -4.046   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.227  -4.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7    4   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetic acid	Generator

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate

Traditional Name

{9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C2OC=C(COC(C)=O)C2=C(C)C2=C(C)C=CC=C12

InChI Identifier

InChI=1S/C18H18O4/c1-10-6-5-7-14-15(10)11(2)16-13(8-21-12(3)19)9-22-18(16)17(14)20-4/h5-7,9H,8H2,1-4H3

InChI Key

QZKFLEVSBJRTEL-UHFFFAOYSA-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Naphthalene
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.21	ALOGPS
logP	3.66	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.86 m³·mol⁻¹	ChemAxon
Polarizability	32.54 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

101634579

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate (NP0224260)

MOL for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

3D MOL for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

3D SDF for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

3D-SDF for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

PDB for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

3D PDB for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

SMILES for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

INCHI for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

Structure for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)

3D Structure for NP0224260 ({9-methoxy-4,5-dimethylnaphtho[2,3-b]furan-3-yl}methyl acetate)