NP-MRD: Showing NP-Card for 4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate (NP0211433)

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Record Information

Version

2.0

Created at

2022-09-05 09:42:45 UTC

Updated at

2022-09-05 09:42:45 UTC

NP-MRD ID

NP0211433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate

Description

4A-hydroxy-3,5-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate 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. 4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate is found in Arctotis hirsuta and Arctotis stoechadifolia. 4A-hydroxy-3,5-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171516502D          

 26 29  0  0  0  0            999 V2000
   -4.2509   -1.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466   -1.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -0.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914   -1.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4302   -1.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    0.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3571   -0.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840   -1.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7696   -1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -2.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -1.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342   -0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0944   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    0.8196    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
  3  5  1  0  0  0  0
  5  6  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1533004171516502D          

 26 29  0  0  0  0            999 V2000
   -4.2509   -1.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466   -1.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -0.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914   -1.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4302   -1.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    0.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3571   -0.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840   -1.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7696   -1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -2.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -1.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342   -0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8826    0.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0944   -0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    0.8196    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
  3  5  1  0  0  0  0
  5  6  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0211433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1CC2C3(CO3)CC3OC(=O)C(=C)C3CC2(O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-5-10(2)17(21)25-14-6-16-19(9-24-19)8-15-13(11(3)18(22)26-15)7-20(16,23)12(14)4/h10,13-16,23H,3-9H2,1-2H3

> <INCHI_KEY>
LEEQHPIPKYKRAR-UHFFFAOYSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.453175534785956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4a-hydroxy-3,5-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.8524017686666654

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.825930094769454

> <JCHEM_PKA_STRONGEST_BASIC>
-3.312338176547841

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
91.84169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3aH-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -7.935  -2.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.434  -2.590   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.386  -1.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.840   0.011   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.885  -1.803   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.431  -3.275   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.837  -0.674   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.336  -1.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.731  -2.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.803  -2.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.146  -0.794   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.215   0.745   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.533  -0.126   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.921  -0.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.263  -2.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.303  -3.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.763  -3.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.878  -5.035   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.491  -4.367   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.797  -2.433   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.403  -1.017   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.904  -0.674   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.243  -0.004   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.381   1.530   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.176  -0.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.314   1.530   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17   19                                                       
CONECT   19   18   17                                                       
CONECT   20   15   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   11    8   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
4a-Hydroxy-3,5-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

4a-hydroxy-3,5-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate

Traditional Name

4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3aH-spiro[azuleno[6,5-b]furan-8,2'-oxirane]-6-yl 2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CC2C3(CO3)CC3OC(=O)C(=C)C3CC2(O)C1=C

InChI Identifier

InChI=1S/C20H26O6/c1-5-10(2)17(21)25-14-6-16-19(9-24-19)8-15-13(11(3)18(22)26-15)7-20(16,23)12(14)4/h10,13-16,23H,3-9H2,1-2H3

InChI Key

LEEQHPIPKYKRAR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arctotis hirsuta	LOTUS Database	35616633
Arctotis stoechadifolia	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
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	1.16	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.84 m³·mol⁻¹	ChemAxon
Polarizability	38.45 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

14285654

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate (NP0211433)

MOL for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

3D MOL for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

3D SDF for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

3D-SDF for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

PDB for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

3D PDB for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

SMILES for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

INCHI for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

Structure for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)

3D Structure for NP0211433 (4a-hydroxy-3,5-dimethylidene-2-oxo-hexahydro-3ah-spiro[azuleno[6,5-b]furan-8,2'-oxiran]-6-yl 2-methylbutanoate)