NP-MRD: Showing NP-Card for 7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate (NP0252229)

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Record Information

Version

2.0

Created at

2022-09-07 15:40:15 UTC

Updated at

2022-09-07 15:40:15 UTC

NP-MRD ID

NP0252229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate

Description

NSC165260 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. 7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate is found in Xylocarpus granatum. Based on a literature review very few articles have been published on NSC165260.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217402D          

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M  END

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M  END


  Mrv1652309072217402D          

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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  6 37  1  0  0  0  0
 24 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/CO)C(=O)OC1C=C(C)C2C3OC(=O)C(=C)C3C(CC3(CO3)C12)OC(=O)C(\COC(C)=O)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O10/c1-6-16(10-28)25(31)35-18-8-13(3)20-22(18)27(12-34-27)9-19(21-14(4)24(30)37-23(20)21)36-26(32)17(7-2)11-33-15(5)29/h6-8,18-23,28H,4,9-12H2,1-3,5H3/b16-6+,17-7+

> <INCHI_KEY>
ARVIDAQMVLXQIX-KGMKFKQSSA-N

> <FORMULA>
C27H32O10

> <MOLECULAR_WEIGHT>
516.543

> <EXACT_MASS>
516.19954723

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.67820578721029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

> <JCHEM_LOGP>
1.8628011589999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.886041332431564

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8486455211944346

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
130.2864

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7-{[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.939   1.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.464  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.369  -1.309   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.909  -1.309   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.464  -2.555   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.001  -2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001  -0.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.205   0.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.862   1.923   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.991   2.970   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.649   4.472   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.463   2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.806   1.015   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.277   0.561   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.592   3.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.249   5.065   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.378   6.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.035   7.614   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.850   5.659   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.706   0.079   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.375  -1.309   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.708  -0.539   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.708  -2.079   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.706  -2.696   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.496  -4.018   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.030  -4.156   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.677  -5.554   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.211  -5.692   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.791  -6.813   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.257  -6.675   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.371  -7.934   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.438  -8.210   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.972  -8.348   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.483  -5.178   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.067  -4.573   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.745  -5.363   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.205  -3.039   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21   23                                                       
CONECT   23   22   21                                                       
CONECT   24   21   25   37                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34   25   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    6   24                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₀

Average Mass

516.5430 Da

Monoisotopic Mass

516.19955 Da

IUPAC Name

7-{[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

Traditional Name

7-{[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/CO)C(=O)OC1C=C(C)C2C3OC(=O)C(=C)C3C(CC3(CO3)C12)OC(=O)C(\COC(C)=O)=C\C

InChI Identifier

InChI=1S/C27H32O10/c1-6-16(10-28)25(31)35-18-8-13(3)20-22(18)27(12-34-27)9-19(21-14(4)24(30)37-23(20)21)36-26(32)17(7-2)11-33-15(5)29/h6-8,18-23,28H,4,9-12H2,1-3,5H3/b16-6+,17-7+

InChI Key

ARVIDAQMVLXQIX-KGMKFKQSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylocarpus granatum	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
Tetracarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	1.86	ChemAxon
pKa (Strongest Acidic)	14.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.29 m³·mol⁻¹	ChemAxon
Polarizability	51.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4572328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5458357

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate (NP0252229)

MOL for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

3D MOL for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

3D SDF for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

3D-SDF for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

PDB for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

3D PDB for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

SMILES for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

INCHI for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

Structure for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)

3D Structure for NP0252229 (7-{[(2e)-2-(hydroxymethyl)but-2-enoyl]oxy}-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-2-[(acetyloxy)methyl]but-2-enoate)