NP-MRD: Showing NP-Card for 5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate (NP0287031)

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Record Information

Version

2.0

Created at

2022-09-09 15:53:54 UTC

Updated at

2022-09-09 15:53:54 UTC

NP-MRD ID

NP0287031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate

Description

5-Methyl-3,8-dimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl acetate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate is found in Stevia ovata. 5-Methyl-3,8-dimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251511212D          

 21 23  0  0  0  0            999 V2000
    6.0115    0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4068    0.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5903    1.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    2.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    1.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    2.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    2.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    2.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326    3.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    2.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    1.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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
  5 10  1  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
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)CCC2C1CC1C(CC2=C)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-9-7-15-13(10(2)16(19)20-15)8-14-12(9)5-6-17(14,4)21-11(3)18/h12-15H,1-2,5-8H2,3-4H3

> <INCHI_KEY>
RFARYQBJLCEXIX-UHFFFAOYSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.623479413336106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-3,8-dimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl acetate

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.4708654836666666

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.63120381341263

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
77.10449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate

> <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      11.222   0.416   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.093   1.464   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.435   2.965   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.621   1.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.492   2.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.568   0.825   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.652   3.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.047   4.487   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.513   4.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.170   2.847   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.783   2.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.395   2.847   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.052   4.349   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.013   5.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.553   5.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.221   6.940   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.519   4.487   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.913   3.071   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.588   2.728   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.073   2.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.935   0.524   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   10                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-3,8-dimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

5-methyl-3,8-dimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl acetate

Traditional Name

5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)CCC2C1CC1C(CC2=C)OC(=O)C1=C

InChI Identifier

InChI=1S/C17H22O4/c1-9-7-15-13(10(2)16(19)20-15)8-14-12(9)5-6-17(14,4)21-11(3)18/h12-15H,1-2,5-8H2,3-4H3

InChI Key

RFARYQBJLCEXIX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stevia ovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.74	ALOGPS
logP	2.47	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.1 m³·mol⁻¹	ChemAxon
Polarizability	30.62 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

13817969

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate (NP0287031)

MOL for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

3D MOL for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

3D SDF for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

3D-SDF for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

PDB for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

3D PDB for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

SMILES for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

INCHI for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

Structure for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)

3D Structure for NP0287031 (5-methyl-3,8-dimethylidene-2-oxo-octahydroazuleno[6,5-b]furan-5-yl acetate)