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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:52:54 UTC

Update Date

2022-03-07 02:54:40 UTC

HMDB ID

HMDB0035858

Secondary Accession Numbers

HMDB35858

Metabolite Identification

Common Name

Obacunone

Description

Obacunone belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review a significant number of articles have been published on Obacunone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02241219542D          

 33 38  0  0  0  0            999 V2000
   -0.8278   -1.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128   -2.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008   -1.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3159   -2.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627    2.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0309    1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    2.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    2.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183    2.9138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0309    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447    0.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4597   -0.8319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4727   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3159   -1.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0035858
     RDKit          3D
Obacunone
 63 68  0  0  0  0  0  0  0  0999 V2000
   -4.7736   -0.7837    1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6065    1.3956    0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.4827   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    3.4501   -0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
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 31 63  1  0
M  END

  Mrv0541 02241219542D          

 33 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0035858

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3

> <INCHI_KEY>
MAYJEFRPIKEYBL-UHFFFAOYSA-N

> <FORMULA>
C26H30O7

> <MOLECULAR_WEIGHT>
454.5122

> <EXACT_MASS>
454.199153314

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
47.09377714221641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.882319155333332

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.92373987219294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.160139226129598

> <JCHEM_POLAR_SURFACE_AREA>
95.34

> <JCHEM_REFRACTIVITY>
116.18639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035858
     RDKit          3D
Obacunone
 63 68  0  0  0  0  0  0  0  0999 V2000
   -4.7736   -0.7837    1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    0.0859    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7827   -0.4331   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6065    1.3956    0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.4827   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    3.4501   -0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    2.5950   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624    1.9124   -0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242    0.9270    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7288    1.7686    1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -0.1553    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.3428   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0655   -1.8122   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7900   -2.8344   -1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -0.9876    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561   -1.4514    1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3498    0.4113   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.4305    0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    1.0408   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -0.3486   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.2401    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260   -0.6413   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010    0.1790   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411    1.3649   -1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    1.7623   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6113    0.8851    0.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7071   -0.0578    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566   -1.9870   -0.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -2.9382   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -3.9965    0.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511   -2.6851   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076   -2.0815   -1.6320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.3289   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434   -1.8170    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6766   -0.3282    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896   -0.8534    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8498   -0.0654   -0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739    0.0609   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8302   -1.5193   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    3.2975   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043    2.1299   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666    2.8511    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    1.6267    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5227    2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -0.5752    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0719   -2.1750   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255   -1.1183   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -2.2805    1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2025   -0.7345    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975   -2.0100    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964    0.3758   -1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    2.3996   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    1.6048    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    0.9428   -1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.7792   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117    0.0846    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3412   -1.1381    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    0.6255    1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610   -0.4073   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7732    1.8566   -2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9927    2.6316   -0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6711   -0.9030    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260   -3.4497    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 11  2  1  0
 33 15  1  0
 17  9  1  0
 33 20  1  0
 27 23  2  0
 33 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 24 60  1  0
 25 61  1  0
 27 62  1  0
 31 63  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.545  -3.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.211  -3.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.121  -3.090   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.456  -3.860   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.544   3.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.791   3.067   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.036   3.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.561   5.439   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.021   5.439   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.791   1.527   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.123   0.757   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.123  -0.783   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.458  -1.553   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.430  -0.015   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.545  -1.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.749  -0.590   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.251  -0.934   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.918  -2.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.251  -3.709   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.458  -2.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.891  -2.888   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.121  -1.553   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.211  -0.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.211   0.760   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.121   1.530   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.456   0.760   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.456   2.297   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.416  -5.439   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.749  -4.053   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.545  -5.013   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.456  -0.780   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.791  -1.553   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.456  -2.323   0.000  0.00  0.00           O+0
CONECT    1    2   15   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3                                                            
CONECT    5    6    9                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    6   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   14   16   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   29                                                       
CONECT   20   18                                                            
CONECT   21   22                                                            
CONECT   22    3   21   23   31                                             
CONECT   23   15   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   10   25   27   31                                             
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29    1   19   28   30                                             
CONECT   30   29                                                            
CONECT   31   22   26   32   33                                             
CONECT   32   12   31   33                                                  
CONECT   33   31   32                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0035858
HETATM    1  C1  UNL     1      -4.774  -0.784   1.471  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.132   0.086   0.380  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.783  -0.433  -0.915  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.606   1.396   0.620  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.347   2.483  -0.236  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.150   3.450  -0.266  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.182   2.595  -1.130  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.062   1.912  -0.962  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.724   0.927   0.104  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.729   1.769   1.395  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.702  -0.155   0.332  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.456  -1.343  -0.616  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.066  -1.812  -0.587  1.00  0.00           C  
HETATM   14  O3  UNL     1      -0.790  -2.834  -1.149  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.023  -0.988   0.154  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.056  -1.451   1.543  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.350   0.411  -0.200  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.714   1.430   0.129  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.934   1.041  -0.660  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.402  -0.349  -0.192  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.809  -0.240   1.242  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.626  -0.641  -0.995  1.00  0.00           C  
HETATM   23  C20 UNL     1       4.801   0.179  -0.603  1.00  0.00           C  
HETATM   24  C21 UNL     1       5.241   1.365  -1.189  1.00  0.00           C  
HETATM   25  C22 UNL     1       6.369   1.762  -0.502  1.00  0.00           C  
HETATM   26  O4  UNL     1       6.611   0.885   0.442  1.00  0.00           O  
HETATM   27  C23 UNL     1       5.707  -0.058   0.408  1.00  0.00           C  
HETATM   28  O5  UNL     1       4.057  -1.987  -0.944  1.00  0.00           O  
HETATM   29  C24 UNL     1       3.201  -2.938  -0.440  1.00  0.00           C  
HETATM   30  O6  UNL     1       3.649  -3.996   0.026  1.00  0.00           O  
HETATM   31  C25 UNL     1       1.751  -2.685  -0.462  1.00  0.00           C  
HETATM   32  O7  UNL     1       1.308  -2.081  -1.632  1.00  0.00           O  
HETATM   33  C26 UNL     1       1.299  -1.329  -0.464  1.00  0.00           C  
HETATM   34  H1  UNL     1      -4.943  -1.817   1.114  1.00  0.00           H  
HETATM   35  H2  UNL     1      -5.677  -0.328   1.873  1.00  0.00           H  
HETATM   36  H3  UNL     1      -3.990  -0.853   2.278  1.00  0.00           H  
HETATM   37  H4  UNL     1      -5.850  -0.065  -0.839  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.374   0.061  -1.795  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.830  -1.519  -0.930  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.268   3.297  -1.977  1.00  0.00           H  
HETATM   41  H8  UNL     1      -1.304   2.130  -1.734  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.667   2.851   1.192  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.686   1.627   1.958  1.00  0.00           H  
HETATM   44  H11 UNL     1      -0.921   1.523   2.071  1.00  0.00           H  
HETATM   45  H12 UNL     1      -2.413  -0.575   1.353  1.00  0.00           H  
HETATM   46  H13 UNL     1      -3.072  -2.175  -0.162  1.00  0.00           H  
HETATM   47  H14 UNL     1      -2.726  -1.118  -1.648  1.00  0.00           H  
HETATM   48  H15 UNL     1      -0.807  -2.280   1.749  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.202  -0.735   2.340  1.00  0.00           H  
HETATM   50  H17 UNL     1       0.897  -2.010   1.810  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.296   0.376  -1.344  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.351   2.400  -0.325  1.00  0.00           H  
HETATM   53  H20 UNL     1       0.905   1.605   1.173  1.00  0.00           H  
HETATM   54  H21 UNL     1       1.666   0.943  -1.731  1.00  0.00           H  
HETATM   55  H22 UNL     1       2.747   1.779  -0.598  1.00  0.00           H  
HETATM   56  H23 UNL     1       2.012   0.085   1.935  1.00  0.00           H  
HETATM   57  H24 UNL     1       3.341  -1.138   1.570  1.00  0.00           H  
HETATM   58  H25 UNL     1       3.536   0.625   1.288  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.461  -0.407  -2.089  1.00  0.00           H  
HETATM   60  H27 UNL     1       4.773   1.857  -2.017  1.00  0.00           H  
HETATM   61  H28 UNL     1       6.993   2.632  -0.661  1.00  0.00           H  
HETATM   62  H29 UNL     1       5.671  -0.903   1.076  1.00  0.00           H  
HETATM   63  H30 UNL     1       1.126  -3.450   0.035  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   11
CONECT    3   37   38   39
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   40
CONECT    8    9   41
CONECT    9   10   11   17
CONECT   10   42   43   44
CONECT   11   12   45
CONECT   12   13   46   47
CONECT   13   14   14   15
CONECT   15   16   17   33
CONECT   16   48   49   50
CONECT   17   18   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   22   33
CONECT   21   56   57   58
CONECT   22   23   28   59
CONECT   23   24   27   27
CONECT   24   25   25   60
CONECT   25   26   61
CONECT   26   27
CONECT   27   62
CONECT   28   29
CONECT   29   30   30   31
CONECT   31   32   33   63
CONECT   32   33
END

HMDB0035858
     RDKit          3D
Obacunone
 63 68  0  0  0  0  0  0  0  0999 V2000
   -4.7736   -0.7837    1.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    0.0859    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7827   -0.4331   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6065    1.3956    0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.4827   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    3.4501   -0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    2.5950   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624    1.9124   -0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242    0.9270    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7288    1.7686    1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -0.1553    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.3428   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0655   -1.8122   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7900   -2.8344   -1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -0.9876    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561   -1.4514    1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3498    0.4113   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.4305    0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    1.0408   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -0.3486   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.2401    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260   -0.6413   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010    0.1790   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411    1.3649   -1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    1.7623   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6113    0.8851    0.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7071   -0.0578    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566   -1.9870   -0.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -2.9382   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -3.9965    0.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511   -2.6851   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076   -2.0815   -1.6320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.3289   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434   -1.8170    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6766   -0.3282    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896   -0.8534    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8498   -0.0654   -0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739    0.0609   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8302   -1.5193   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    3.2975   -1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043    2.1299   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666    2.8511    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    1.6267    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5227    2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -0.5752    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0719   -2.1750   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255   -1.1183   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -2.2805    1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2025   -0.7345    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8975   -2.0100    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964    0.3758   -1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    2.3996   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    1.6048    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    0.9428   -1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    1.7792   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117    0.0846    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3412   -1.1381    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    0.6255    1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610   -0.4073   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7732    1.8566   -2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9927    2.6316   -0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6711   -0.9030    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260   -3.4497    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 11  2  1  0
 33 15  1  0
 17  9  1  0
 33 20  1  0
 27 23  2  0
 33 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 24 60  1  0
 25 61  1  0
 27 62  1  0
 31 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Casimirolide	HMDB
Obacunoic acid, eta-lactone	HMDB
Tricoccin S3	HMDB

Chemical Formula

C₂₆H₃₀O₇

Average Molecular Weight

454.5122

Monoisotopic Molecular Weight

454.199153314

IUPAC Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

Traditional Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

CAS Registry Number

751-03-1

SMILES

CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1

InChI Identifier

InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3

InChI Key

MAYJEFRPIKEYBL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Dicarboxylic acid or derivatives
Pyran
Oxane
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035858)

Source

Endogenous

Endogenous (HMDB: HMDB0035858)

Plant

Plant (HMDB: HMDB0035858)

Animal

Animal (HMDB: HMDB0035858)

Exogenous

Food

Food (HMDB: HMDB0035858)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sour orange (FooDB: FOOD00918)

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035858)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035858)

Lipid metabolism pathway (HMDB: HMDB0035858)

Cellular process

Cell signaling (HMDB: HMDB0035858)

Biochemical process

Lipid transport (HMDB: HMDB0035858)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035858)

Agriculture

Pesticide (HMDB: HMDB0035858)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 - 230 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	3.76	ALOGPS
logP	3.88	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.92	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.19 m³·mol⁻¹	ChemAxon
Polarizability	47.09 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.272	31661259
DarkChem	[M-H]-	194.903	31661259
DeepCCS	[M-2H]-	240.196	30932474
DeepCCS	[M+Na]+	215.768	30932474
AllCCS	[M+H]+	206.6	32859911
AllCCS	[M+H-H2O]+	204.4	32859911
AllCCS	[M+NH4]+	208.6	32859911
AllCCS	[M+Na]+	209.1	32859911
AllCCS	[M-H]-	212.8	32859911
AllCCS	[M+Na-2H]-	213.7	32859911
AllCCS	[M+HCOO]-	214.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Obacunone	CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	4381.9	Standard polar	33892256
Obacunone	CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	3017.5	Standard non polar	33892256
Obacunone	CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	3923.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Obacunone,1TMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3562.3	Semi standard non polar	33892256
Obacunone,1TMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3115.8	Standard non polar	33892256
Obacunone,1TBDMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3810.6	Semi standard non polar	33892256
Obacunone,1TBDMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3322.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Obacunone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g3-4763900000-f92282a5dc1cc0f37780	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Obacunone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 10V, Negative-QTOF	splash10-0pb9-0001900000-91f82701dfbe9c1b8937	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 20V, Negative-QTOF	splash10-0pbi-0002900000-67e1b74e789b5b5f69bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 40V, Negative-QTOF	splash10-016s-9006000000-9e9ffb6bdd1b887e9452	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 10V, Negative-QTOF	splash10-0ufr-0000900000-2a1dbb5cddee36a5b409	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 20V, Negative-QTOF	splash10-0udi-0000900000-f1afb1f1fe1011d9791e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 40V, Negative-QTOF	splash10-0kk9-1023900000-aeeeda4f35507c3c79e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 10V, Positive-QTOF	splash10-0a4i-0002900000-e1ec4288c41df91d3ba3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 20V, Positive-QTOF	splash10-000i-0025900000-6a379fce8acd6dafc36d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 40V, Positive-QTOF	splash10-0f6t-9324100000-2e07d772eab4f19d665e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 10V, Positive-QTOF	splash10-0a4i-0000900000-edd8aed905ca850e4d7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 20V, Positive-QTOF	splash10-0a4i-0044900000-ce3894bf62d35dff6da5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Obacunone 40V, Positive-QTOF	splash10-03xu-2952200000-55cb094ddec8d0b8027d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

500031

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1852111

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Obacunone (HMDB0035858)

MOL for HMDB0035858 (Obacunone)

3D MOL for HMDB0035858 (Obacunone)

3D SDF for HMDB0035858 (Obacunone)

3D-SDF for HMDB0035858 (Obacunone)

PDB for HMDB0035858 (Obacunone)

3D PDB for HMDB0035858 (Obacunone)

SMILES for HMDB0035858 (Obacunone)

INCHI for HMDB0035858 (Obacunone)

Structure for HMDB0035858 (Obacunone)

3D Structure for HMDB0035858 (Obacunone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra