NP-MRD: Showing NP-Card for 9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione (NP0319771)

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Record Information

Version

2.0

Created at

2022-09-11 20:58:38 UTC

Updated at

2022-09-11 20:58:38 UTC

NP-MRD ID

NP0319771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione

Description

9-[2-(Furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodec-4-ene-3,11-dione belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Based on a literature review very few articles have been published on 9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodec-4-ene-3,11-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112222582D          

 24 27  0  0  0  0            999 V2000
    0.0978   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192   -2.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -4.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940   -4.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -3.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0732   -0.4181    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 13 23  1  0  0  0  0
  9 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)C2OC(=O)C3=CCCC(C23C)C1(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-12-16(21)17-20(3)14(18(22)24-17)5-4-6-15(20)19(12,2)9-7-13-8-10-23-11-13/h5,8,10-12,15,17H,4,6-7,9H2,1-3H3

> <INCHI_KEY>
CFELHBJGZFKRSN-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.7105065652778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-3,11-dione

> <JCHEM_LOGP>
4.336708533666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.54244909234039

> <JCHEM_PKA_STRONGEST_BASIC>
-2.784123947100777

> <JCHEM_POLAR_SURFACE_AREA>
56.510000000000005

> <JCHEM_REFRACTIVITY>
89.58990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-3,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.182  -1.890   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.504   1.174   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.412  -3.596   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.974  -3.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.649  -4.829   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.788  -6.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.315  -7.553   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.101  -8.501   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.176  -7.640   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.249  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.737  -0.780   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13    2   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   13    9    5   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-3,11-dione

Traditional Name

9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-3,11-dione

CAS Registry Number

Not Available

SMILES

CC1C(=O)C2OC(=O)C3=CCCC(C23C)C1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C20H24O4/c1-12-16(21)17-20(3)14(18(22)24-17)5-4-6-15(20)19(12,2)9-7-13-8-10-23-11-13/h5,8,10-12,15,17H,4,6-7,9H2,1-3H3

InChI Key

CFELHBJGZFKRSN-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 alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Gamma butyrolactone
Furan
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Lactone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
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	4.34	ChemAxon
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.59 m³·mol⁻¹	ChemAxon
Polarizability	34.71 Å³	ChemAxon
Number of Rings	4	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

163028413

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione (NP0319771)

MOL for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

3D MOL for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

3D SDF for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

3D-SDF for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

PDB for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

3D PDB for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

SMILES for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

INCHI for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

Structure for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)

3D Structure for NP0319771 (9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-ene-3,11-dione)