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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:19 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034719

Secondary Accession Numbers

HMDB34719

Metabolite Identification

Common Name

Isoamberboin

Description

Isoamberboin 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 Isoamberboin.

Structure

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

HMDB0034719
     RDKit          3D
Isoamberboin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0396    2.6647   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    1.8326   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311    2.4792    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176    1.5388    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    2.3002    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.4384   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.0725   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.1635   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.7310    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -0.8894    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193   -1.1448    1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154   -0.7984    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.4968    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137   -1.7881    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -2.7900    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921   -1.2401    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057   -1.8577    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9486    0.1958   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    0.4007   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    2.3586   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    3.7250   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    2.9753    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    3.3153   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    1.1228    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.5822   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1934    0.6956   -1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.7330   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -1.2918   -1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0584   -0.9622   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096   -2.1519   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235   -1.6307   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -0.1488    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871   -2.2048   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -2.7616    1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -2.7066    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -3.8100    0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.8051    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    0.4536   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2315    0.0240   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv0541 05061308022D          

 19 21  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034719

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7-9,11-14,17H,1,4-5H2,2-3H3

> <INCHI_KEY>
ZAPNUFCAIXITRW-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.746095486152285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
1.0128339806666657

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.52619752852935

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.770021737166523

> <JCHEM_PKA_STRONGEST_BASIC>
-2.899355869504146

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
68.6285

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,9-dimethyl-6-methylidene-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034719
     RDKit          3D
Isoamberboin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0396    2.6647   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    1.8326   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311    2.4792    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176    1.5388    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    2.3002    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.4384   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.0725   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.1635   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.7310    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -0.8894    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193   -1.1448    1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154   -0.7984    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.4968    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137   -1.7881    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -2.7900    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921   -1.2401    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057   -1.8577    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9486    0.1958   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    0.4007   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    2.3586   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    3.7250   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    2.9753    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    3.3153   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    1.1228    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.5822   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1934    0.6956   -1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.7330   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -1.2918   -1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0584   -0.9622   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096   -2.1519   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235   -1.6307   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -0.1488    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871   -2.2048   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -2.7616    1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -2.7066    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -3.8100    0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.8051    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    0.4536   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2315    0.0240   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  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       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.347   6.030   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.888   4.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.576   5.139   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.651   4.588   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    6   11                                                       
CONECT    5    9   10                                                       
CONECT    6    1    4    9                                                  
CONECT    7    2   10   12                                                  
CONECT    8    3   13   15                                                  
CONECT    9    5    6   12                                                  
CONECT   10    5    7   16                                                  
CONECT   11    4   13   17                                                  
CONECT   12    7    9   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13   19                                                  
CONECT   15    8   18   19                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   15                                                            
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0034719
HETATM    1  C1  UNL     1      -2.040   2.665  -0.927  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.129   1.833  -0.451  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.031   2.479   0.184  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.118   1.539   0.587  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.305   2.300   0.686  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.387   0.438  -0.385  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.815  -0.072  -0.175  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.131  -1.164  -1.163  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.637  -0.731   1.169  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.483  -0.889   2.063  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.319  -1.145   1.239  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.615  -0.798   0.057  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.817  -0.497   0.363  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.614  -1.788   0.125  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.404  -2.790   1.206  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.992  -1.240   0.082  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.006  -1.858   0.316  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.949   0.196  -0.295  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.470   0.401  -0.658  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.954   2.359  -1.423  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.874   3.725  -0.820  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.353   2.975   1.122  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.413   3.315  -0.440  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.956   1.123   1.603  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.593   2.582  -0.223  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.193   0.696  -1.430  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.548   0.733  -0.145  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.307  -1.292  -1.922  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.058  -0.962  -1.742  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.310  -2.152  -0.655  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.723  -1.631  -0.646  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.013  -0.149   1.376  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.387  -2.205  -0.879  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.180  -2.762   1.999  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.377  -2.707   1.621  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.434  -3.810   0.723  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.106   0.805   0.629  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.614   0.454  -1.116  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.231   0.024  -1.651  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4   22   23
CONECT    4    5    6   24
CONECT    5   25
CONECT    6    7   12   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   31
CONECT   13   14   19   32
CONECT   14   15   16   33
CONECT   15   34   35   36
CONECT   16   17   17   18
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0034719
     RDKit          3D
Isoamberboin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0396    2.6647   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    1.8326   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311    2.4792    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176    1.5388    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    2.3002    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.4384   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.0725   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.1635   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.7310    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -0.8894    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193   -1.1448    1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154   -0.7984    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.4968    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137   -1.7881    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -2.7900    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9921   -1.2401    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057   -1.8577    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9486    0.1958   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    0.4007   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    2.3586   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    3.7250   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    2.9753    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    3.3153   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    1.1228    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.5822   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1934    0.6956   -1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.7330   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -1.2918   -1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0584   -0.9622   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096   -2.1519   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235   -1.6307   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -0.1488    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871   -2.2048   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -2.7616    1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -2.7066    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -3.8100    0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    0.8051    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    0.4536   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2315    0.0240   -1.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 12  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Maximolide	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

4-hydroxy-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

Traditional Name

4-hydroxy-3,9-dimethyl-6-methylidene-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

CAS Registry Number

30825-69-5

SMILES

CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7-9,11-14,17H,1,4-5H2,2-3H3

InChI Key

ZAPNUFCAIXITRW-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
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034719)

Source

Endogenous

Endogenous (HMDB: HMDB0034719)

Plant

Plant (HMDB: HMDB0034719)

Animal

Animal (HMDB: HMDB0034719)

Exogenous

Food

Food (HMDB: HMDB0034719)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0034719)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034719)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034719)

Lipid metabolism pathway (HMDB: HMDB0034719)

Cellular process

Cell signaling (HMDB: HMDB0034719)

Biochemical process

Lipid transport (HMDB: HMDB0034719)

Role

Biological role

Energy source (HMDB: HMDB0034719)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034719)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °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	9.31 g/L	ALOGPS
logP	0.07	ALOGPS
logP	1.01	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.63 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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]+	161.865	31661259
DarkChem	[M-H]-	156.791	31661259
DeepCCS	[M+H]+	162.701	30932474
DeepCCS	[M-H]-	160.343	30932474
DeepCCS	[M-2H]-	193.229	30932474
DeepCCS	[M+Na]+	168.794	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	165.6	32859911
AllCCS	[M+Na-2H]-	165.5	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoamberboin	CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O	3179.3	Standard polar	33892256
Isoamberboin	CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O	2232.6	Standard non polar	33892256
Isoamberboin	CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O	2326.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoamberboin,1TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(=O)CC12	2189.5	Semi standard non polar	33892256
Isoamberboin,1TMS,isomer #2	C=C1CC(O)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2242.7	Semi standard non polar	33892256
Isoamberboin,1TMS,isomer #3	C=C1CC(O)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2175.8	Semi standard non polar	33892256
Isoamberboin,2TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2307.1	Semi standard non polar	33892256
Isoamberboin,2TMS,isomer #1	C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC12	2194.2	Standard non polar	33892256
Isoamberboin,2TMS,isomer #2	C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2233.2	Semi standard non polar	33892256
Isoamberboin,2TMS,isomer #2	C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC12	2166.8	Standard non polar	33892256
Isoamberboin,1TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(=O)CC12	2419.1	Semi standard non polar	33892256
Isoamberboin,1TBDMS,isomer #2	C=C1CC(O)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2473.4	Semi standard non polar	33892256
Isoamberboin,1TBDMS,isomer #3	C=C1CC(O)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2392.2	Semi standard non polar	33892256
Isoamberboin,2TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2749.2	Semi standard non polar	33892256
Isoamberboin,2TBDMS,isomer #1	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2665.2	Standard non polar	33892256
Isoamberboin,2TBDMS,isomer #2	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2682.2	Semi standard non polar	33892256
Isoamberboin,2TBDMS,isomer #2	C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2546.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamberboin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-4890000000-4bb6e591faf985f8ff52	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamberboin GC-MS (1 TMS) - 70eV, Positive	splash10-00bl-6292000000-83863fb6e3cabe054ba5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamberboin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamberboin 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 - Isoamberboin 10V, Positive-QTOF	splash10-00kb-0190000000-6f9be36c3aa34356b55e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 20V, Positive-QTOF	splash10-00tb-0590000000-7bcb4c36e43bdcf3da35	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 40V, Positive-QTOF	splash10-0uxu-7920000000-6571f853883151dd24e3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 10V, Negative-QTOF	splash10-03di-0090000000-430712af8274b9f42ef7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 20V, Negative-QTOF	splash10-03xs-0190000000-3d05bced3f4b105a24f5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 40V, Negative-QTOF	splash10-0f6x-8910000000-919bc9093d0895c8f608	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 20V, Negative-QTOF	splash10-03xu-0490000000-777fb4db99d8c24a3e2b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 40V, Negative-QTOF	splash10-006y-2970000000-b8efa1d1bb870369fe13	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 10V, Positive-QTOF	splash10-00mk-0090000000-7b21369ee9fade9011ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 20V, Positive-QTOF	splash10-004j-0390000000-8d2fa4bd23943ef0dae6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamberboin 40V, Positive-QTOF	splash10-00kr-2970000000-b9332d5a4e19fcd17190	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB013256

KNApSAcK ID

C00020538

Chemspider ID

35013778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14589063

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Isoamberboin (HMDB0034719)

MOL for HMDB0034719 (Isoamberboin)

3D MOL for HMDB0034719 (Isoamberboin)

3D SDF for HMDB0034719 (Isoamberboin)

3D-SDF for HMDB0034719 (Isoamberboin)

PDB for HMDB0034719 (Isoamberboin)

3D PDB for HMDB0034719 (Isoamberboin)

SMILES for HMDB0034719 (Isoamberboin)

INCHI for HMDB0034719 (Isoamberboin)

Structure for HMDB0034719 (Isoamberboin)

3D Structure for HMDB0034719 (Isoamberboin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra