NP-MRD: Showing NP-Card for (3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0198731)

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Record Information

Version

1.0

Created at

2022-09-04 17:13:28 UTC

Updated at

2022-09-04 17:13:29 UTC

NP-MRD ID

NP0198731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate

Description

(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate is found in Achillea millefolium, Artemisia deserti, Artemisia tilesii and Lactuca serriola. It was first documented in 2012 (PMID: 36070501). Based on a literature review a significant number of articles have been published on (3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate (PMID: 36070500) (PMID: 36070964) (PMID: 36070963) (PMID: 36070962) (PMID: 36070959) (PMID: 36070958).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    4.2814   -0.3816    2.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.2900    2.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859   -0.7590    3.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    0.3194    1.0984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222    0.4429    0.8194 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6013    1.8924    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204    2.1550    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    3.5663   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    1.3294   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.7088   -0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    2.8740   -0.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7597    0.4769   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526   -0.5354   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598   -1.9478   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -0.1326    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6759   -0.8564   -0.6195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5091   -2.1381   -0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -2.5536   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242   -3.6907    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140   -1.4417   -0.6977 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8629   -1.5862   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.2649   -0.4803 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7352   -1.0930    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833    0.5977    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -0.7985    3.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085   -0.0317    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    2.5196    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    2.2102    1.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1194    3.6135   -1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271    4.0115    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    4.2184    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7624    0.4190   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418   -1.9822    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -2.2567   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7965   -2.6184    0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811   -0.2884    1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369   -0.9384   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545   -1.2932   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.7960   -2.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4787   -2.5575   -2.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9469   -1.5584   -2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450    0.4357   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  0
 22 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 18 20  1  0
  9 15  1  0
  5 22  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 20 38  1  1
 22 42  1  6
 16 37  1  6
 15 36  1  1
 14 33  1  0
 14 34  1  0
 14 35  1  0
 12 32  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  6 27  1  0
  6 28  1  0
  5 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652309042219132D          

 22 24  0  0  1  0            999 V2000
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  2  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 20  1  6  0  0  0
  5 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@@H](OC1=O)[C@@H]1C(C)=CC(=O)C1=C(C)C[C@@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3/t9-,12-,14+,15+,16-/m0/s1

> <INCHI_KEY>
QONYNSMAVSRIRD-HFDOBSEUSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.435791682273788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_LOGP>
1.5625007430000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.018362697577242

> <JCHEM_PKA_STRONGEST_BASIC>
-5.352192106566

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
79.43849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.530   1.186   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.343   0.879   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   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(3S,3AR,4S,9ar,9BS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@@H](OC1=O)[C@@H]1C(C)=CC(=O)C1=C(C)C[C@@H]2OC(C)=O

InChI Identifier

InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3/t9-,12-,14+,15+,16-/m0/s1

InChI Key

QONYNSMAVSRIRD-HFDOBSEUSA-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
Achillea millefolium	LOTUS Database	35616633
Artemisia deserti	LOTUS Database	35616633
Artemisia tilesii	LOTUS Database	35616633
Lactuca serriola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
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	1.56	ChemAxon
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	31.44 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

162944841

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Thalidomide. 2012. [PubMed:36070501 ]
Authors unspecified: Lenalidomide. 2012. [PubMed:36070500 ]
Uehara M, Wada-Hiraike O, Koga K, Yamamoto N, Hirano M, Harada M, Hirota Y, Osuga Y: Prediction of the final menstrual period in women taking Dienogest using estradiol and follicle-stimulating hormone values: a case-control study. Endocr J. 2022 Sep 7. doi: 10.1507/endocrj.EJ22-0158. [PubMed:36070964 ]
Oginosawa Y: Validation of the Implantable Cardioverter-Defibrillators Indication Criteria for Nonischemic Cardiomyopathy- Why? When? How? Circ J. 2022 Sep 6. doi: 10.1253/circj.CJ-22-0478. [PubMed:36070963 ]
Kodera S, Morita H, Nishi H, Takeda N, Ando J, Komuro I: Cost-Effectiveness of Dapagliflozin for Chronic Kidney Disease in Japan. Circ J. 2022 Sep 6. doi: 10.1253/circj.CJ-22-0086. [PubMed:36070962 ]
Niwa R, Ichi S, Nomura R, Sato K: Hypofractionated Stereotactic Radiotherapy with CyberKnife for Large Arteriovenous Malformations and Arteriovenous Malformations Located in Eloquent Areas. Neurol Med Chir (Tokyo). 2022 Oct 15;62(10):445-450. doi: 10.2176/jns-nmc.2022-0033. Epub 2022 Sep 6. [PubMed:36070959 ]
Cohen RB, Severance G, Olafson SN, Ward CL, Parsikia A, Bloom AR, Moran B, Kaplan MJ, Leung P: Laparoscopic Cholecystectomy in the Time of Coronavirus: A Level-1 Trauma Center's Experience. Am Surg. 2022 Sep 7:31348221121552. doi: 10.1177/00031348221121552. [PubMed:36070958 ]
Fujino A, Tanaka Y, Abe D, Ariizumi Y, Inaji M, Maehara T: A New Technique for the Endoscopic Reconstruction of Skull Base Defects Using Multiple-balloon Catheters. Neurol Med Chir (Tokyo). 2022 Oct 15;62(10):483-487. doi: 10.2176/jns-nmc.2022-0146. Epub 2022 Sep 6. [PubMed:36070960 ]
Hara R, Hasegawa E, Inoue N, Sekine A, Tanaka K, Ikuma D, Mizuno H, Oba Y, Yamanouchi M, Suwabe T, Sawa N, Kono K, Kinowaki K, Ohashi K, Ubara Y, Hoshino J: Crescentic Glomerulonephritis with Fibrinoid Vasculitis after Administration of Influenza Vaccine. Intern Med. 2023 Apr 1;62(7):1077-1080. doi: 10.2169/internalmedicine.9410-22. Epub 2022 Sep 6. [PubMed:36070955 ]
Teranishi K, Mishima Y, Taniguchi T, Fujii T, Nonaka S, Kitamura T, Kondo A, Oishi H: Preliminary Experience of the Surpass Streamline Flow Diverter for Large and Giant Unruptured Internal Carotid Artery Aneurysms. Neurol Med Chir (Tokyo). 2022 Oct 15;62(10):451-457. doi: 10.2176/jns-nmc.2022-0167. Epub 2022 Sep 6. [PubMed:36070961 ]
Futamura M, Ozaki Y, Makino H, Tsujimoto S, Shigesaka M, Tanaka A, Shimamoto K, Son Y, Ito T, Nomura S: Anti-MDA-5 Antibody-positive Dermatomyositis after Allogeneic Bone Marrow Transplantation for Acute Transformation of Chronic Myelogenous Leukemia. Intern Med. 2023 Apr 1;62(7):1081-1087. doi: 10.2169/internalmedicine.9529-22. Epub 2022 Sep 6. [PubMed:36070956 ]
Goto R, Kawakami H, Horiuchi Y, Chikada A, Yasuda T, Suzuki T, Miyazato Y, Ishikane M, Kishino Y, Miyazaki H, Igari T, Katano H, Suzuki T, Murayama S, Arai N: An Autopsy Report of a Case with Cerebral Infarction Complicated by Coronavirus Disease 2019 Infection. Intern Med. 2022 Nov 15;61(22):3439-3444. doi: 10.2169/internalmedicine.9726-22. Epub 2022 Sep 6. [PubMed:36070957 ]
Hamada O, Tsutsumi T, Imanaka Y: Efficiency of the Japanese Hospitalist System for Patients with Urinary Tract Infection: A Propensity-matched Analysis. Intern Med. 2023 Apr 15;62(8):1131-1138. doi: 10.2169/internalmedicine.8944-21. Epub 2022 Sep 6. [PubMed:36070954 ]
Naito T: Will the Introduction of the Hospitalist System Save Japan? Intern Med. 2023 Apr 15;62(8):1105-1106. doi: 10.2169/internalmedicine.0693-22. Epub 2022 Sep 6. [PubMed:36070953 ]
Isaac S, Pasha MA, Thinagaran JKR, Kyei-Nimako E: Letter to the editor: Delayed Metastasis of Renal Cell Carcinoma. Intern Med. 2023 May 1;62(9):1385. doi: 10.2169/internalmedicine.0674-22. Epub 2022 Sep 6. [PubMed:36070952 ]
Yokoyama T, Hayashi D, Kosugi S: Nocardia Subcutaneous Abscess in a Waldenstrom Macroglobulinemia Patient. Intern Med. 2023 Apr 15;62(8):1247-1248. doi: 10.2169/internalmedicine.0496-22. Epub 2022 Sep 6. [PubMed:36070951 ]
LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0198731)

MOL for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D MOL for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D SDF for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D-SDF for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

PDB for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D PDB for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

SMILES for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

INCHI for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

Structure for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D Structure for NP0198731 ((3s,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)