NP-MRD: Showing NP-Card for [8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate (NP0243751)

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Record Information

Version

2.0

Created at

2022-09-07 04:22:20 UTC

Updated at

2022-09-07 04:22:20 UTC

NP-MRD ID

NP0243751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate

Description

[8-(Acetyloxy)-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. [8-(Acetyloxy)-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251504262D          

 26 28  0  0  0  0            999 V2000
   -0.5463   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -1.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -3.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -2.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4761   -1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235   -0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    0.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0847   -1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -2.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958   -2.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7974   -3.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -3.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -4.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051   -5.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9370   -4.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654   -5.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849   -4.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5691   -4.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -3.9193    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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END


  Mrv1533004251504262D          

 26 28  0  0  0  0            999 V2000
   -0.5463   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -1.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -3.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -2.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4761   -1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235   -0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    0.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0847   -1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -2.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958   -2.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7974   -3.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -3.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -4.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051   -5.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9370   -4.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654   -5.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849   -4.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5691   -4.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -3.9193    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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OCC1=C2CC(OC(C)=O)C(=C)C2C2OC(=O)C(=C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-5-17(22)24-9-13-6-7-14-10(2)20(23)26-19(14)18-11(3)16(8-15(13)18)25-12(4)21/h14,16,18-19H,2-3,5-9H2,1,4H3

> <INCHI_KEY>
TYMFAPVKTZAHEP-UHFFFAOYSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.426976173148674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[8-(acetyloxy)-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.0448681663333326

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.489872827664888

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
92.9974

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[8-(acetyloxy)-3,9-dimethylidene-2-oxo-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.020  -5.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.314  -5.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.648  -5.010   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.648  -3.470   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.981  -5.780   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.315  -5.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.649  -5.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.921  -4.913   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.898  -3.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.355  -2.875   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.809  -1.404   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.311  -1.061   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.765   0.411   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.358  -2.190   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.279  -4.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.819  -4.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.393  -5.367   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.955  -6.800   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.462  -7.121   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.623  -8.652   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.956  -9.422   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.216  -9.278   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.895 -10.785   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.185  -8.134   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.662  -8.364   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.534  -7.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    7                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
[8-(Acetyloxy)-3,9-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,7H,8H,9H,9ah,9BH-azuleno[4,5-b]furan-6-yl]methyl propanoic acid	Generator

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

[8-(acetyloxy)-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate

Traditional Name

[8-(acetyloxy)-3,9-dimethylidene-2-oxo-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-6-yl]methyl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OCC1=C2CC(OC(C)=O)C(=C)C2C2OC(=O)C(=C)C2CC1

InChI Identifier

InChI=1S/C20H24O6/c1-5-17(22)24-9-13-6-7-14-10(2)20(23)26-19(14)18-11(3)16(8-15(13)18)25-12(4)21/h14,16,18-19H,2-3,5-9H2,1,4H3

InChI Key

TYMFAPVKTZAHEP-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 tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.26	ALOGPS
logP	2.04	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93 m³·mol⁻¹	ChemAxon
Polarizability	38.43 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	Yes	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

14262524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate (NP0243751)

MOL for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

3D MOL for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

3D SDF for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

3D-SDF for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

PDB for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

3D PDB for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

SMILES for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

INCHI for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

Structure for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)

3D Structure for NP0243751 ([8-(acetyloxy)-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-6-yl]methyl propanoate)