NP-MRD: Showing NP-Card for (3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0328357)

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Record Information

Version

2.0

Created at

2022-09-12 11:45:30 UTC

Updated at

2022-09-12 11:45:31 UTC

NP-MRD ID

NP0328357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione

Description

(3AS,6R,6aS,9aS,9bS)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione 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. (3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione is found in Artemisia rutifolia and Schistostephium umbellatum. Based on a literature review very few articles have been published on (3aS,6R,6aS,9aS,9bS)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    4.0605    0.5730    0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    0.9327    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    2.2519   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330    3.2901   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187    2.1912   -0.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    0.8215   -0.2302 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6393    0.0845    0.4018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7243   -1.2868   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7261   -2.1640    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994   -1.8085    0.2287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0663   -1.7906   -1.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -2.8897    0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.6223    0.9946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6742   -0.5457    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963   -1.4152    1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9203    0.6895    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    1.4182   -0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323    2.7281   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    0.7028    0.6205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4647    1.4410    1.8029 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892    1.2370    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -0.4416    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    0.6294   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4187   -0.0160    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -1.6898    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036   -1.2924   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9319   -2.2065    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763   -3.2158    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -2.7505   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -1.0207   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -1.6183   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6034   -3.5871    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -0.8475    2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9038    0.9469   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1324    3.4604   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7280    3.2172   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597    2.6807   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716    1.9128    2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 19  1  0
 19 20  1  1
 19  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 19 17  1  0
  7  6  1  0
 10 13  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 16 34  1  0
 13 33  1  1
 20 38  1  0
  6 23  1  6
  1 21  1  0
  1 22  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
M  END


  Mrv1652309122213452D          

 20 22  0  0  1  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3265   -2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -1.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2319    0.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  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  6  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  6 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@@H]2[C@@]1(O)[C@H]1OC(=O)C(=C)[C@@H]1CC[C@@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-7-6-10(16)11-14(3,18)5-4-9-8(2)13(17)20-12(9)15(7,11)19/h6,9,11-12,18-19H,2,4-5H2,1,3H3/t9-,11-,12-,14+,15+/m0/s1

> <INCHI_KEY>
VXENIKHPXCFDEG-CPSKLWFRSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.086974974407447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6R,6aS,9aS,9bS)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_LOGP>
0.794677351

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.397171287584637

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.559859801669667

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0215778092282006

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
70.65859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6R,6aS,9aS,9bS)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.343  -4.649   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.146  -3.148   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.616  -1.954   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.033   0.914   0.000  0.00  0.00           O+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   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    6   13   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)[C@@H]2[C@@]1(O)[C@H]1OC(=O)C(=C)[C@@H]1CC[C@@]2(C)O

InChI Identifier

InChI=1S/C15H18O5/c1-7-6-10(16)11-14(3,18)5-4-9-8(2)13(17)20-12(9)15(7,11)19/h6,9,11-12,18-19H,2,4-5H2,1,3H3/t9-,11-,12-,14+,15+/m0/s1

InChI Key

VXENIKHPXCFDEG-CPSKLWFRSA-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
Artemisia rutifolia	LOTUS Database	35616633
Schistostephium umbellatum	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
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

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

162902995

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0328357)

MOL for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D MOL for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D SDF for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D-SDF for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

PDB for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D PDB for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

SMILES for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

INCHI for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

Structure for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D Structure for NP0328357 ((3as,6r,6as,9as,9bs)-6,9a-dihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,9bh-azuleno[4,5-b]furan-2,7-dione)