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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 02:27:40 UTC

Update Date

2021-09-24 02:27:40 UTC

HMDB ID

HMDB0303513

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cumambrin A

Description

Cumambrin a belongs to guaianolides and derivatives class of compounds. Those 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. Cumambrin a is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cumambrin a can be found in sweet bay, which makes cumambrin a a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303513
     RDKit          3D
Cumambrin A
 44 46  0  0  0  0  0  0  0  0999 V2000
    1.9622    2.6873    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    2.2914    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535    3.0756   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    4.2466   -0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    2.2624   -1.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.8869   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    1.0080   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.1845    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -0.3487   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -0.5019    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834   -0.6692   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.4991    1.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -1.3968   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -1.7859    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -3.1894    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.9614    1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.9161    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.2387   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    0.0003   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    1.0126    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015    2.3817    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5446    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    3.6842    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    2.0888    1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147    0.2587   -1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.0453   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.1733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6844   -1.3957    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7645    0.2633    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.1354   -1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.3062   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -2.2335   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -3.1536   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -3.9127    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709   -3.4829    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242   -2.8062    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146   -1.0100    1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -1.4455   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659   -2.0785    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6513   -0.0008   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4429    2.3011    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    2.9149    1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453    2.9008   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.9716    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
  7  2  1  0
 22 17  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END


  Mrv0541 02241217522D          

 22 24  0  0  0  0            999 V2000
    0.5070   -2.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1010   -1.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2315   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205   -0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5070   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -0.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5553    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5553    1.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2655    2.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002    1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    1.3523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900   -1.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180   -1.1108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303513

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CC(C)(O)C2CC=C(C)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3

> <INCHI_KEY>
XMJROHDIQQOWTO-UHFFFAOYSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.3536

> <EXACT_MASS>
306.146723814

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.254031878651915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.0729297373333337

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.669974721206124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.943153056944441

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
79.6271

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303513
     RDKit          3D
Cumambrin A
 44 46  0  0  0  0  0  0  0  0999 V2000
    1.9622    2.6873    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    2.2914    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535    3.0756   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    4.2466   -0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    2.2624   -1.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.8869   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    1.0080   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.1845    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -0.3487   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -0.5019    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834   -0.6692   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.4991    1.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -1.3968   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -1.7859    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -3.1894    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.9614    1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.9161    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.2387   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    0.0003   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    1.0126    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015    2.3817    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5446    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    3.6842    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    2.0888    1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147    0.2587   -1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.0453   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.1733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6844   -1.3957    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7645    0.2633    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.1354   -1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.3062   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -2.2335   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -3.1536   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -3.9127    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709   -3.4829    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242   -2.8062    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146   -1.0100    1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -1.4455   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659   -2.0785    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6513   -0.0008   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4429    2.3011    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    2.9149    1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453    2.9008   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.9716    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
  7  2  1  0
 22 17  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  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       0.946  -3.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.217  -2.434   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.660  -1.803   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.922  -2.614   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.922   0.721   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.389   1.172   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.299  -0.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.307  -1.442   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.225  -1.262   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.946  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.479  -0.270   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.405   1.442   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.037   1.983   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.037   3.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.496   3.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.307   2.705   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.840   2.705   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.201   2.524   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.848  -2.975   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.020  -2.975   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.922  -2.975   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.020  -2.073   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   13   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    2    8   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11    3   10                                                       
CONECT   12   10   13   16                                                  
CONECT   13    6   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    6                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0303513
HETATM    1  C1  UNL     1       1.962   2.687   0.876  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.010   2.291   0.072  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.153   3.076  -0.329  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.480   4.247  -0.020  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.926   2.262  -1.188  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.635   0.887  -0.850  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.859   1.008  -0.615  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.418  -0.185   0.066  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.770  -0.349  -0.408  1.00  0.00           O  
HETATM   10  C7  UNL     1       3.790  -0.502   0.481  1.00  0.00           C  
HETATM   11  C8  UNL     1       5.183  -0.669  -0.048  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.540  -0.499   1.708  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.605  -1.397  -0.422  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.484  -1.786   0.497  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.945  -3.189   0.083  1.00  0.00           C  
HETATM   16  O5  UNL     1       0.083  -1.961   1.780  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.657  -0.916   0.574  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.767  -1.239  -0.402  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.594   0.000  -0.316  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.842   1.013   0.107  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.401   2.382   0.289  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.435   0.545   0.346  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.965   3.684   1.334  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.816   2.089   1.160  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.915   0.259  -1.697  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.308   1.045  -1.638  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.398  -0.173   1.170  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.684  -1.396   0.640  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.764   0.263   0.014  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.176  -1.135  -1.048  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.298  -1.306  -1.463  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.356  -2.233  -0.405  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.065  -3.154  -1.036  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.158  -3.913   0.384  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.871  -3.483   0.585  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.624  -2.806   1.704  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.115  -1.010   1.600  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.407  -1.445  -1.412  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.366  -2.078   0.020  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.651  -0.001  -0.578  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.443   2.301   0.666  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.820   2.915   1.067  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.445   2.901  -0.674  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.038   0.972   1.297  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   22   25
CONECT    7    8   26
CONECT    8    9   13   27
CONECT    9   10
CONECT   10   11   12   12
CONECT   11   28   29   30
CONECT   13   14   31   32
CONECT   14   15   16   17
CONECT   15   33   34   35
CONECT   16   36
CONECT   17   18   22   37
CONECT   18   19   38   39
CONECT   19   20   20   40
CONECT   20   21   22
CONECT   21   41   42   43
CONECT   22   44
END

HMDB0303513
     RDKit          3D
Cumambrin A
 44 46  0  0  0  0  0  0  0  0999 V2000
    1.9622    2.6873    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    2.2914    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535    3.0756   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    4.2466   -0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    2.2624   -1.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352    0.8869   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    1.0080   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.1845    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -0.3487   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -0.5019    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834   -0.6692   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.4991    1.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -1.3968   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -1.7859    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -3.1894    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.9614    1.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.9161    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.2387   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    0.0003   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    1.0126    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015    2.3817    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5446    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    3.6842    1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    2.0888    1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147    0.2587   -1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.0453   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.1733    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6844   -1.3957    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7645    0.2633    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763   -1.1354   -1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.3062   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -2.2335   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -3.1536   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -3.9127    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709   -3.4829    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242   -2.8062    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146   -1.0100    1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -1.4455   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659   -2.0785    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6513   -0.0008   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4429    2.3011    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    2.9149    1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453    2.9008   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.9716    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
  7  2  1  0
 22 17  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Molecular Weight

306.3536

Monoisotopic Molecular Weight

306.146723814

IUPAC Name

6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(C)(O)C2CC=C(C)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3

InChI Key

XMJROHDIQQOWTO-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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.85	ALOGPS
logP	1.07	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.63 m³·mol⁻¹	ChemAxon
Polarizability	32.25 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
AllCCS	[M+H]+	171.537	32859911
AllCCS	[M+H-H2O]+	168.371	32859911
AllCCS	[M+Na]+	175.309	32859911
AllCCS	[M+NH4]+	174.468	32859911
AllCCS	[M-H]-	175.622	32859911
AllCCS	[M+Na-2H]-	175.609	32859911
AllCCS	[M+HCOO]-	175.722	32859911
DeepCCS	[M-2H]-	199.315	30932474
DeepCCS	[M+Na]+	174.542	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 10V, Positive-QTOF	splash10-052r-0092000000-a3259d364f6bf1cbac83	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 20V, Positive-QTOF	splash10-00mt-1390000000-2deac8051828e5e12e51	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 40V, Positive-QTOF	splash10-0zir-9430000000-bb6d8a44f5b2042e9ba8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 10V, Negative-QTOF	splash10-0bt9-1096000000-ff0e08a34d66bfd2bf88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 20V, Negative-QTOF	splash10-0bta-2091000000-8acb853ab2299a84e783	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 40V, Negative-QTOF	splash10-0a4i-9760000000-62ca9278d25eacf10663	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 10V, Positive-QTOF	splash10-0002-0091000000-4406db4cdf6a92a5ddb2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 20V, Positive-QTOF	splash10-004i-0090000000-a27c1dde8186109f22c5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 40V, Positive-QTOF	splash10-0adi-4970000000-8c0bea446d30b2daed3f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 10V, Negative-QTOF	splash10-0002-1090000000-5df0faa16f9eddb5f073	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 20V, Negative-QTOF	splash10-01ot-2090000000-2fb783e139f74a31dca4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cumambrin A 40V, Negative-QTOF	splash10-052e-5290000000-701d45aa8c76f95476b9	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB015385

KNApSAcK ID

Not Available

Chemspider ID

3036246

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3809323

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

Not Available

Showing metabocard for Cumambrin A (HMDB0303513)

MOL for HMDB0303513 (Cumambrin A)

3D MOL for HMDB0303513 (Cumambrin A)

3D SDF for HMDB0303513 (Cumambrin A)

3D-SDF for HMDB0303513 (Cumambrin A)

PDB for HMDB0303513 (Cumambrin A)

3D PDB for HMDB0303513 (Cumambrin A)

SMILES for HMDB0303513 (Cumambrin A)

INCHI for HMDB0303513 (Cumambrin A)

Structure for HMDB0303513 (Cumambrin A)

3D Structure for HMDB0303513 (Cumambrin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra