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Showing metabocard for Deguelin (HMDB0250941)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:05:54 UTC
Update Date2021-09-26 23:02:40 UTC
HMDB IDHMDB0250941
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeguelin
DescriptionAC1LCSZE belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. AC1LCSZE is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Deguelin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Deguelin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250941 (Deguelin)


  Mrv1533004171516212D          

 29 33  0  0  0  0            999 V2000
   -1.3480   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -4.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -5.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
Download

3D MOL for HMDB0250941 (Deguelin)

HMDB0250941
     RDKit          3D
Deguelin
 51 55  0  0  0  0  0  0  0  0999 V2000
    7.5600    1.0929   -0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7798    0.3065    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    0.2832    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046    1.0282   -0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.9402   -0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5717    0.1070    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793   -0.6389    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -0.5564    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566   -1.3417    1.7937 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945   -2.1936    2.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1199    0.1035    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.0409    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773   -2.0810    1.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -0.9303    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317   -1.6799    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053   -1.5532    1.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -0.6537    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208    0.1003   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0448   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485    0.7094   -0.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    0.2689   -1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    1.1928   -2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376    1.7124   -1.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557    1.0253   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639    1.1543   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8542    0.3760   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6667    1.3084    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8211   -0.3718   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1634   -0.4933    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3111    2.1660   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3746    0.9261   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6204    0.9465   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105    1.6934   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437   -1.2985    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078   -2.9896    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -1.6414    3.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5989   -2.7328    3.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7637    1.0314    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -2.3539    2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -2.1343    2.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177   -0.7744   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258    2.0073   -2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    0.5945   -2.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    1.6100   -1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4578    1.8351   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0585    2.1738    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5680    0.7100    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1113    1.5771    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5713    0.3976   -1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3908   -1.1313   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -0.7422   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8  3  1  0
 21 11  1  0
 23  5  1  0
 19 14  1  0
 29 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 16 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END
Download

3D SDF for HMDB0250941 (Deguelin)


  Mrv1533004171516212D          

 29 33  0  0  0  0            999 V2000
   -1.3480   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -4.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -5.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250941

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3

> <INCHI_KEY>
ORDAZKGHSNRHTD-UHFFFAOYSA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.423

> <EXACT_MASS>
394.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.69366716763747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.3042058106666667

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.724479793029548

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204904948066979

> <JCHEM_POLAR_SURFACE_AREA>
63.22

> <JCHEM_REFRACTIVITY>
107.21799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0250941 (Deguelin)

HMDB0250941
     RDKit          3D
Deguelin
 51 55  0  0  0  0  0  0  0  0999 V2000
    7.5600    1.0929   -0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7798    0.3065    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    0.2832    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046    1.0282   -0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.9402   -0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5717    0.1070    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793   -0.6389    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -0.5564    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566   -1.3417    1.7937 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945   -2.1936    2.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1199    0.1035    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.0409    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773   -2.0810    1.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -0.9303    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317   -1.6799    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053   -1.5532    1.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -0.6537    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208    0.1003   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0448   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8485    0.7094   -0.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    0.2689   -1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    1.1928   -2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376    1.7124   -1.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557    1.0253   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639    1.1543   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8542    0.3760   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6667    1.3084    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8211   -0.3718   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1634   -0.4933    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3111    2.1660   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3746    0.9261   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6204    0.9465   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105    1.6934   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9437   -1.2985    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078   -2.9896    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -1.6414    3.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5989   -2.7328    3.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7637    1.0314    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -2.3539    2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -2.1343    2.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177   -0.7744   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6258    2.0073   -2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    0.5945   -2.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    1.6100   -1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4578    1.8351   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0585    2.1738    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5680    0.7100    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1113    1.5771    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5713    0.3976   -1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3908   -1.1313   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -0.7422   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8  3  1  0
 21 11  1  0
 23  5  1  0
 19 14  1  0
 29 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 16 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END
Download

PDB for HMDB0250941 (Deguelin)

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -2.516  -9.804   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874  -5.803   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.414  -5.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.724  -7.136   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.293  -7.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.293  -9.460   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.344  -9.804   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.414 -11.137   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.746 -11.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END
Download

3D PDB for HMDB0250941 (Deguelin)

COMPND    HMDB0250941
HETATM    1  C1  UNL     1       7.560   1.093  -0.817  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.780   0.306   0.024  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.394   0.283   0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.605   1.028  -0.784  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.217   0.940  -0.706  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.572   0.107   0.188  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.379  -0.639   1.006  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.773  -0.556   0.934  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.557  -1.342   1.794  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.895  -2.194   2.708  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.120   0.103   0.177  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.429  -1.041   0.765  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.877  -2.081   1.250  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.053  -0.930   0.776  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.832  -1.680   1.636  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.205  -1.553   1.620  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.798  -0.654   0.719  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.021   0.100  -0.146  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.630  -0.045  -0.112  1.00  0.00           C  
HETATM   20  O4  UNL     1      -0.849   0.709  -0.978  1.00  0.00           O  
HETATM   21  C17 UNL     1       0.499   0.269  -1.212  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.245   1.193  -2.095  1.00  0.00           C  
HETATM   23  O5  UNL     1       2.438   1.712  -1.549  1.00  0.00           O  
HETATM   24  C19 UNL     1      -3.656   1.025  -1.070  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.964   1.154  -1.094  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.854   0.376  -0.194  1.00  0.00           C  
HETATM   27  C22 UNL     1      -6.667   1.308   0.701  1.00  0.00           C  
HETATM   28  C23 UNL     1      -6.821  -0.372  -1.089  1.00  0.00           C  
HETATM   29  O6  UNL     1      -5.163  -0.493   0.667  1.00  0.00           O  
HETATM   30  H1  UNL     1       7.311   2.166  -0.611  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.375   0.926  -1.893  1.00  0.00           H  
HETATM   32  H3  UNL     1       8.620   0.946  -0.563  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.111   1.693  -1.496  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.944  -1.299   1.723  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.308  -2.990   2.171  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.154  -1.641   3.329  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.599  -2.733   3.363  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.764   1.031   0.727  1.00  0.00           H  
HETATM   39  H10 UNL     1      -1.315  -2.354   2.305  1.00  0.00           H  
HETATM   40  H11 UNL     1      -3.824  -2.134   2.288  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.418  -0.774  -1.627  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.626   2.007  -2.527  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.571   0.594  -2.998  1.00  0.00           H  
HETATM   44  H15 UNL     1      -3.062   1.610  -1.740  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.458   1.835  -1.772  1.00  0.00           H  
HETATM   46  H17 UNL     1      -7.059   2.174   0.152  1.00  0.00           H  
HETATM   47  H18 UNL     1      -7.568   0.710   1.024  1.00  0.00           H  
HETATM   48  H19 UNL     1      -6.111   1.577   1.613  1.00  0.00           H  
HETATM   49  H20 UNL     1      -7.571   0.398  -1.433  1.00  0.00           H  
HETATM   50  H21 UNL     1      -7.391  -1.131  -0.535  1.00  0.00           H  
HETATM   51  H22 UNL     1      -6.266  -0.742  -1.953  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   33
CONECT    5    6    6   23
CONECT    6    7   11
CONECT    7    8    8   34
CONECT    8    9
CONECT    9   10
CONECT   10   35   36   37
CONECT   11   12   21   38
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   29
CONECT   18   19   19   24
CONECT   19   20
CONECT   20   21
CONECT   21   22   41
CONECT   22   23   42   43
CONECT   24   25   25   44
CONECT   25   26   45
CONECT   26   27   28   29
CONECT   27   46   47   48
CONECT   28   49   50   51
END
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SMILES for HMDB0250941 (Deguelin)

COC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O
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INCHI for HMDB0250941 (Deguelin)

InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC23H22O6
Average Molecular Weight394.423
Monoisotopic Molecular Weight394.141638428
IUPAC Name17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one
Traditional Name17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O
InChI Identifier
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3
InChI KeyORDAZKGHSNRHTD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassRotenoids
Direct ParentRotenones
Alternative Parents
Substituents
  • Rotenone or derivatives
  • 8-prenylated isoflavanone
  • Isoflavanone
  • Isoflavan
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.93ALOGPS
logP3.3ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity107.22 m³·mol⁻¹ChemAxon
Polarizability41.69 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+199.52530932474
DeepCCS[M-H]-197.16730932474
DeepCCS[M-2H]-230.96530932474
DeepCCS[M+Na]+206.19330932474
AllCCS[M+H]+195.632859911
AllCCS[M+H-H2O]+193.132859911
AllCCS[M+NH4]+197.932859911
AllCCS[M+Na]+198.632859911
AllCCS[M-H]-195.332859911
AllCCS[M+Na-2H]-194.832859911
AllCCS[M+HCOO]-194.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DeguelinCOC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O4729.9Standard polar33892256
DeguelinCOC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O3241.0Standard non polar33892256
DeguelinCOC1=CC2=C(C=C1OC)C1C(CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O3149.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deguelin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0539000000-d126e3ff881cf8223adc2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deguelin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 10V, Positive-QTOFsplash10-0002-0009000000-6ed5b18b5f3c115b5f262021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 20V, Positive-QTOFsplash10-0002-0019000000-e8d8075977e641977d3c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 40V, Positive-QTOFsplash10-000f-2958000000-e95ee8be5b2fd7daddf32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 10V, Negative-QTOFsplash10-0006-0009000000-637dd3eddf57f64880702021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 20V, Negative-QTOFsplash10-0006-0009000000-d91cffef59ca103334e62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deguelin 40V, Negative-QTOFsplash10-0006-0249000000-c1778d6c2b28711ec7a72021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound606171
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]