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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:45:23 UTC

Update Date

2022-03-07 02:54:37 UTC

HMDB ID

HMDB0035740

Secondary Accession Numbers

HMDB35740

Metabolite Identification

Common Name

Arlatin

Description

Arlatin 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. Based on a literature review a small amount of articles have been published on Arlatin.

Structure

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

HMDB0035740
     RDKit          3D
Arlatin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.3071    3.2814   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    1.9327   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5305   -1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.1468   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8448    0.0355    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.4513    1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    0.8343    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.5713    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.7269   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8218    1.3611   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.1582   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.1154    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306   -0.7126   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594   -0.4781   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -1.8935    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -1.7522    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4821    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068   -1.7002    2.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -2.1336   -0.1836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    3.6100    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    3.3788   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541    4.0091   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3079    2.0644   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -0.5185   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    0.0094   -1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.5794    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    1.4513    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    0.5404    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1222   -0.3838    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    0.0426   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4113   -1.1408   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361   -1.5531   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -0.4543   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -2.6481   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.2196    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -1.4345   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0188    1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.7794    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -1.3194    2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -1.1602    2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406   -2.8172   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  8  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv0541 05061308412D          

 19 21  0  0  0  0            999 V2000
    2.6763   -0.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    3.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    2.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    2.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    1.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    1.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    2.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851    2.5113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5679    2.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035740

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-4-7-15(18)11(8)12-10(5-6-14(15,3)17)9(2)13(16)19-12/h4,9-12,17-18H,5-7H2,1-3H3

> <INCHI_KEY>
VBQMPXNFLQSHMH-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.5442658109126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,6a-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
0.8683161206666672

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.71400936503122

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.181413324582387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3022050719309686

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.49739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,6a-dihydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035740
     RDKit          3D
Arlatin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.3071    3.2814   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    1.9327   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5305   -1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.1468   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8448    0.0355    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.4513    1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    0.8343    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.5713    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.7269   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8218    1.3611   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.1582   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.1154    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306   -0.7126   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594   -0.4781   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -1.8935    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -1.7522    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4821    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068   -1.7002    2.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -2.1336   -0.1836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    3.6100    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    3.3788   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541    4.0091   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3079    2.0644   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -0.5185   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    0.0094   -1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.5794    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    1.4513    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    0.5404    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1222   -0.3838    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    0.0426   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4113   -1.1408   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361   -1.5531   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -0.4543   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -2.6481   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.2196    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -1.4345   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0188    1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.7794    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -1.3194    2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -1.1602    2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406   -2.8172   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  8  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.996  -0.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.530   3.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.343   6.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.970   1.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.461   4.688   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.073   5.356   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.901   2.645   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.455   0.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.245   2.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.803   3.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.303   1.982   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.843   1.982   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.176   1.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.686   4.688   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.343   3.186   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.380   0.147   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.146   4.688   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.927   3.792   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.691   0.697   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    7    8                                                       
CONECT    5    6   10                                                       
CONECT    6    5   14                                                       
CONECT    7    4   15                                                       
CONECT    8    1    4   11                                                  
CONECT    9    2   10   13                                                  
CONECT   10    5    9   12                                                  
CONECT   11    8   12   15                                                  
CONECT   12   10   11   19                                                  
CONECT   13    9   16   19                                                  
CONECT   14    3    6   15   17                                             
CONECT   15    7   11   14   18                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0035740
HETATM    1  C1  UNL     1      -0.307   3.281  -0.717  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.925   1.933  -0.626  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.859   1.531  -1.469  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.289   0.147  -1.140  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.845   0.035   0.289  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.918   0.451   1.065  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.626   0.834   0.386  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.739   0.571   0.412  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.484   1.727  -0.080  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.822   1.361  -0.010  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.774   2.158  -0.069  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.933  -0.115   0.146  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.931  -0.713  -0.819  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.559  -0.478  -0.289  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.112  -1.894   0.207  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.282  -1.752   0.419  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.637  -1.482   0.649  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.207  -1.700   2.046  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.583  -2.134  -0.184  1.00  0.00           O  
HETATM   20  H1  UNL     1       0.140   3.610   0.254  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.407   3.379  -1.552  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.154   4.009  -0.890  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.308   2.064  -2.308  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.768  -0.518  -1.849  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.384   0.009  -1.254  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.750   0.579   0.567  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.828   1.451   1.343  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.184   0.540   1.470  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.122  -0.384   1.188  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.640   0.043  -1.212  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.411  -1.141  -1.702  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.436  -1.553  -0.300  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.464  -0.454  -1.385  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.396  -2.648  -0.588  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.747  -2.220   1.061  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.419  -1.435  -0.649  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.066  -1.019   1.255  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.377  -2.779   2.156  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.478  -1.319   2.818  1.00  0.00           H  
HETATM   40  H21 UNL     1      -3.152  -1.160   2.086  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.141  -2.817  -0.724  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    7
CONECT    3    4   23
CONECT    4    5   24   25
CONECT    5    6    7   17
CONECT    6   26
CONECT    7    8   27
CONECT    8    9   14   28
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   14   29
CONECT   13   30   31   32
CONECT   14   15   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18   19
CONECT   18   38   39   40
CONECT   19   41
END

HMDB0035740
     RDKit          3D
Arlatin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.3071    3.2814   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    1.9327   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5305   -1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.1468   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8448    0.0355    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.4513    1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    0.8343    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.5713    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.7269   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8218    1.3611   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.1582   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331   -0.1154    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306   -0.7126   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594   -0.4781   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -1.8935    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816   -1.7522    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4821    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068   -1.7002    2.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -2.1336   -0.1836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403    3.6100    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    3.3788   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541    4.0091   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3079    2.0644   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -0.5185   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    0.0094   -1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.5794    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    1.4513    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    0.5404    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1222   -0.3838    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    0.0426   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4113   -1.1408   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361   -1.5531   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -0.4543   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -2.6481   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.2196    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -1.4345   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0188    1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -2.7794    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -1.3194    2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -1.1602    2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406   -2.8172   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  8  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

6,6a-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

6,6a-dihydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

93552-69-3

SMILES

CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O

InChI Identifier

InChI=1S/C15H22O4/c1-8-4-7-15(18)11(8)12-10(5-6-14(15,3)17)9(2)13(16)19-12/h4,9-12,17-18H,5-7H2,1-3H3

InChI Key

VBQMPXNFLQSHMH-UHFFFAOYSA-N

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
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 - 205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5371 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.73 g/L	ALOGPS
logP	1.07	ALOGPS
logP	0.87	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.5 m³·mol⁻¹	ChemAxon
Polarizability	28.54 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.89	31661259
DarkChem	[M-H]-	157.963	31661259
DeepCCS	[M+H]+	165.408	30932474
DeepCCS	[M-H]-	163.05	30932474
DeepCCS	[M-2H]-	195.936	30932474
DeepCCS	[M+Na]+	171.502	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	167.2	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arlatin	CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O	3329.9	Standard polar	33892256
Arlatin	CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O	2127.1	Standard non polar	33892256
Arlatin	CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O	2237.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arlatin,1TMS,isomer #1	CC1=CCC2(O)C1C1OC(=O)C(C)C1CCC2(C)O[Si](C)(C)C	2215.6	Semi standard non polar	33892256
Arlatin,1TMS,isomer #2	CC1=CCC2(O[Si](C)(C)C)C1C1OC(=O)C(C)C1CCC2(C)O	2228.7	Semi standard non polar	33892256
Arlatin,2TMS,isomer #1	CC1=CCC2(O[Si](C)(C)C)C1C1OC(=O)C(C)C1CCC2(C)O[Si](C)(C)C	2261.8	Semi standard non polar	33892256
Arlatin,1TBDMS,isomer #1	CC1=CCC2(O)C1C1OC(=O)C(C)C1CCC2(C)O[Si](C)(C)C(C)(C)C	2442.8	Semi standard non polar	33892256
Arlatin,1TBDMS,isomer #2	CC1=CCC2(O[Si](C)(C)C(C)(C)C)C1C1OC(=O)C(C)C1CCC2(C)O	2438.6	Semi standard non polar	33892256
Arlatin,2TBDMS,isomer #1	CC1=CCC2(O[Si](C)(C)C(C)(C)C)C1C1OC(=O)C(C)C1CCC2(C)O[Si](C)(C)C(C)(C)C	2699.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arlatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-9360000000-77dddb226ce20fa9459b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arlatin GC-MS (2 TMS) - 70eV, Positive	splash10-014i-1936000000-9820ee134186d5c7b79e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arlatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arlatin 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 - Arlatin 10V, Positive-QTOF	splash10-014i-0190000000-da151b50e5ad2242b95d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 20V, Positive-QTOF	splash10-0uxv-6690000000-ba1eb4e43f117966d419	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 40V, Positive-QTOF	splash10-0udl-9310000000-430317c052595121c237	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 10V, Negative-QTOF	splash10-014i-0090000000-80b8955c599ab86a2885	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 20V, Negative-QTOF	splash10-01ba-0090000000-603644a22759348cb5ea	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 40V, Negative-QTOF	splash10-0f6t-8910000000-16167a8b3965547084d2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 10V, Positive-QTOF	splash10-0002-0090000000-3268231dbc495ba71be4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 20V, Positive-QTOF	splash10-01ba-3390000000-4b288fd0f4f4e0ae2408	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 40V, Positive-QTOF	splash10-0fvi-9200000000-a1673f2fabbd054f2420	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 10V, Negative-QTOF	splash10-014i-0090000000-dd4b6a7f3e24cfb4ac28	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 20V, Negative-QTOF	splash10-014i-0090000000-a42d0ade52cf3e1fa641	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arlatin 40V, Negative-QTOF	splash10-06tb-6590000000-3fb26c7ef0ff8cd85682	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB014469

KNApSAcK ID

C00020536

Chemspider ID

35014011

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751858

PDB ID

Not Available

ChEBI ID

174499

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1851331

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 ]
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Showing metabocard for Arlatin (HMDB0035740)

MOL for HMDB0035740 (Arlatin)

3D MOL for HMDB0035740 (Arlatin)

3D SDF for HMDB0035740 (Arlatin)

3D-SDF for HMDB0035740 (Arlatin)

PDB for HMDB0035740 (Arlatin)

3D PDB for HMDB0035740 (Arlatin)

SMILES for HMDB0035740 (Arlatin)

INCHI for HMDB0035740 (Arlatin)

Structure for HMDB0035740 (Arlatin)

3D Structure for HMDB0035740 (Arlatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra