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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:38:44 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036489

Secondary Accession Numbers

HMDB36489

Metabolite Identification

Common Name

Dihydrocumambrin A

Description

Dihydrocumambrin A 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 Dihydrocumambrin A.

Structure

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

HMDB0036489
     RDKit          3D
Dihydrocumambrin A
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.6575   -2.1394    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4069   -1.4998   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.0924   -1.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -1.3066    0.4498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194   -0.6829   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.7512   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659   -1.4608   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -1.3361   -2.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -2.5602   -1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -0.2416   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -0.4093   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    0.5657    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    0.8455    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759    1.7706    2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734    0.0971    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    1.0181    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    2.0532   -0.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    2.7075   -0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791    3.9039   -0.4765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5257    1.7116    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789    2.3301    0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    0.5233    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -3.2387   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.9882    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -1.7558   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4302   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977   -2.6410   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -2.1282    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -1.6793   -3.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -1.9814   -2.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2860   -2.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288   -3.3132   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.6053   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6443   -0.0401   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6956   -1.4305   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8493    0.9904    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    1.9490    2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    1.3774    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.7685    2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7736    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    1.5672    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246    1.4083   -0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037    3.3767    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925    1.7416    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    2.4182    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153    0.4373    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
M  END


  Mrv0541 05061309112D          

 22 24  0  0  0  0            999 V2000
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  0  0  0  0
 17  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036489

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O5/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/h5,9,11-15,20H,6-7H2,1-4H3

> <INCHI_KEY>
ACKIMLHJQRKFGM-UHFFFAOYSA-N

> <FORMULA>
C17H24O5

> <MOLECULAR_WEIGHT>
308.3695

> <EXACT_MASS>
308.162373878

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.746817302870674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
0.9312750329999995

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.67057039449124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.942892509449532

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
79.82369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036489
     RDKit          3D
Dihydrocumambrin A
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.6575   -2.1394    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4069   -1.4998   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.0924   -1.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -1.3066    0.4498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194   -0.6829   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.7512   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659   -1.4608   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -1.3361   -2.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -2.5602   -1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -0.2416   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -0.4093   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    0.5657    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    0.8455    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759    1.7706    2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734    0.0971    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    1.0181    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    2.0532   -0.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    2.7075   -0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791    3.9039   -0.4765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5257    1.7116    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789    2.3301    0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    0.5233    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -3.2387   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.9882    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -1.7558   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4302   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977   -2.6410   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -2.1282    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -1.6793   -3.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -1.9814   -2.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2860   -2.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288   -3.3132   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.6053   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6443   -0.0401   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6956   -1.4305   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8493    0.9904    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    1.9490    2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    1.3774    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.7685    2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7736    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    1.5672    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246    1.4083   -0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037    3.3767    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925    1.7416    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    2.4182    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153    0.4373    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  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       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7   12   17                                                       
CONECT    8    1    5   13                                                  
CONECT    9    2   14   16                                                  
CONECT   10    3   18   21                                                  
CONECT   11    6   13   17                                                  
CONECT   12    7   14   21                                                  
CONECT   13    8   11   15                                                  
CONECT   14    9   12   15                                                  
CONECT   15   13   14   22                                                  
CONECT   16    9   19   22                                                  
CONECT   17    4    7   11   20                                             
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0036489
HETATM    1  C1  UNL     1       4.657  -2.139   0.147  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.407  -1.500  -0.308  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.369  -1.092  -1.516  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.289  -1.307   0.450  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.119  -0.683  -0.055  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.069  -1.751  -0.101  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.066  -1.461  -1.024  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.510  -1.336  -2.429  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.923  -2.560  -1.010  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.852  -0.242  -0.692  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.338  -0.409  -0.836  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.853   0.566   0.173  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.918   0.846   1.060  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.076   1.771   2.200  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.673   0.097   0.755  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.526   1.018   0.879  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.727   2.053  -0.100  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.464   2.707  -0.210  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.679   3.904  -0.476  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.526   1.712   0.053  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.579   2.330   0.936  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.828   0.523   0.723  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.608  -3.239  -0.073  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.861  -1.988   1.221  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.518  -1.756  -0.456  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.351  -0.430  -1.112  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.598  -2.641  -0.568  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.233  -2.128   0.897  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.307  -1.679  -3.127  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.373  -1.981  -2.588  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.242  -0.286  -2.684  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.529  -3.313  -1.529  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.511   0.605  -1.299  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.644  -0.040  -1.836  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.696  -1.430  -0.666  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.849   0.990   0.186  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.162   1.949   2.448  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.564   1.377   3.124  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.646   2.769   2.015  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.659  -0.774   1.428  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.637   1.567   1.863  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.925   1.408  -0.934  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.304   3.377   1.190  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.793   1.742   1.844  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.508   2.418   0.312  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.315   0.437   1.727  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   26
CONECT    6    7   27   28
CONECT    7    8    9   10
CONECT    8   29   30   31
CONECT    9   32
CONECT   10   11   15   33
CONECT   11   12   34   35
CONECT   12   13   13   36
CONECT   13   14   15
CONECT   14   37   38   39
CONECT   15   16   40
CONECT   16   17   22   41
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   42
CONECT   21   43   44   45
CONECT   22   46
END

HMDB0036489
     RDKit          3D
Dihydrocumambrin A
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.6575   -2.1394    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4069   -1.4998   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.0924   -1.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -1.3066    0.4498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194   -0.6829   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.7512   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659   -1.4608   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103   -1.3361   -2.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -2.5602   -1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -0.2416   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -0.4093   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    0.5657    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    0.8455    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759    1.7706    2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734    0.0971    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    1.0181    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    2.0532   -0.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    2.7075   -0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791    3.9039   -0.4765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5257    1.7116    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789    2.3301    0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    0.5233    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -3.2387   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615   -1.9882    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -1.7558   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4302   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977   -2.6410   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -2.1282    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -1.6793   -3.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -1.9814   -2.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2860   -2.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288   -3.3132   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.6053   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6443   -0.0401   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6956   -1.4305   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8493    0.9904    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    1.9490    2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    1.3774    3.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.7685    2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592   -0.7736    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    1.5672    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246    1.4083   -0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037    3.3767    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925    1.7416    1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    2.4182    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153    0.4373    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₇H₂₄O₅

Average Molecular Weight

308.3695

Monoisotopic Molecular Weight

308.162373878

IUPAC Name

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

Traditional Name

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

CAS Registry Number

20482-39-7

SMILES

CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O

InChI Identifier

InChI=1S/C17H24O5/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/h5,9,11-15,20H,6-7H2,1-4H3

InChI Key

ACKIMLHJQRKFGM-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
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
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

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036489)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036489)

Source

Endogenous

Endogenous (HMDB: HMDB0036489)

Plant

Plant (HMDB: HMDB0036489)

Animal

Animal (HMDB: HMDB0036489)

Exogenous

Food

Food (HMDB: HMDB0036489)

Vegetable

Leaf vegetable

Garland chrysanthemum (FooDB: FOOD00333)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036489)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036489)

Cellular process

Cell signaling (HMDB: HMDB0036489)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036489)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036489)

Nutrient

Nutrient (HMDB: HMDB0036489)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036489)

Emulsifier (HMDB: HMDB0036489)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3287 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	1.36 g/L	ALOGPS
logP	1.91	ALOGPS
logP	0.93	ChemAxon
logS	-2.4	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	79.82 m³·mol⁻¹	ChemAxon
Polarizability	32.75 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]+	171.026	31661259
DarkChem	[M-H]-	164.85	31661259
DeepCCS	[M+H]+	170.94	30932474
DeepCCS	[M-H]-	168.582	30932474
DeepCCS	[M-2H]-	201.514	30932474
DeepCCS	[M+Na]+	177.033	30932474
AllCCS	[M+H]+	172.3	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocumambrin A	CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O	3333.6	Standard polar	33892256
Dihydrocumambrin A	CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O	2195.9	Standard non polar	33892256
Dihydrocumambrin A	CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O	2359.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocumambrin A,1TMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C)C2CC=C(C)C2C2OC(=O)C(C)C12	2348.3	Semi standard non polar	33892256
Dihydrocumambrin A,1TBDMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C(C)(C)C)C2CC=C(C)C2C2OC(=O)C(C)C12	2567.3	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 - Dihydrocumambrin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9860000000-104795f98b0c33627401	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocumambrin A GC-MS (1 TMS) - 70eV, Positive	splash10-003r-9443000000-91401c9ab14e4ac8009b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocumambrin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocumambrin A 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 - Dihydrocumambrin A 10V, Positive-QTOF	splash10-052f-0092000000-489191966006ead33170	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 20V, Positive-QTOF	splash10-00ke-2390000000-1d46c1bda60df51c738c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 40V, Positive-QTOF	splash10-0zis-9430000000-0fa03c36feb0bd5c7177	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 10V, Negative-QTOF	splash10-0a4i-1096000000-e03b5ce353d5e66eb1c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 20V, Negative-QTOF	splash10-0aos-2091000000-954e88f2eed442a9a585	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 40V, Negative-QTOF	splash10-0a4r-9860000000-10ed4fc2709c0a4e5fcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 10V, Negative-QTOF	splash10-014i-0090000000-faa0ebdf2eb54c037133	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 20V, Negative-QTOF	splash10-00kb-1090000000-443ff4fbf53f388eec1a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 40V, Negative-QTOF	splash10-052f-9350000000-ebd82ffe85af8e68a4c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 10V, Positive-QTOF	splash10-0002-0091000000-57e3cd3e2a5804c8eabc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 20V, Positive-QTOF	splash10-053s-1191000000-8b70ce5493aa2a5ec5a2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocumambrin A 40V, Positive-QTOF	splash10-0007-9320000000-e738c439503e4120a5c6	2021-09-24	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

FDB015386

KNApSAcK ID

C00020480

Chemspider ID

35014159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13895575

PDB ID

Not Available

ChEBI ID

174948

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855571

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 Dihydrocumambrin A (HMDB0036489)

MOL for HMDB0036489 (Dihydrocumambrin A)

3D MOL for HMDB0036489 (Dihydrocumambrin A)

3D SDF for HMDB0036489 (Dihydrocumambrin A)

3D-SDF for HMDB0036489 (Dihydrocumambrin A)

PDB for HMDB0036489 (Dihydrocumambrin A)

3D PDB for HMDB0036489 (Dihydrocumambrin A)

SMILES for HMDB0036489 (Dihydrocumambrin A)

INCHI for HMDB0036489 (Dihydrocumambrin A)

Structure for HMDB0036489 (Dihydrocumambrin A)

3D Structure for HMDB0036489 (Dihydrocumambrin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra