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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:51 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030756

Secondary Accession Numbers

HMDB30756

Metabolite Identification

Common Name

13alpha-Hydroxydolineone

Description

13alpha-Hydroxydolineone 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. Thus, 13alpha-hydroxydolineone is considered to be a flavonoid. 13alpha-Hydroxydolineone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make 13alpha-hydroxydolineone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 13alpha-Hydroxydolineone.

Structure

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


  Mrv0541 05061305292D          

 26 31  0  0  0  0            999 V2000
    5.9868    3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464    3.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946    5.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    5.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    6.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514    4.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9183    4.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896    4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755    5.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    5.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    4.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    5.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323    4.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    4.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082    3.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4132    4.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5113    4.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    6.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003    3.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    4.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806    5.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  1  0  0  0  0
 23  7  1  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
M  END

HMDB0030756
     RDKit          3D
13alpha-Hydroxydolineone
 38 43  0  0  0  0  0  0  0  0999 V2000
   -0.4194    0.6829    2.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856    0.6469    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253    0.2947    0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -0.1129    1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.4471    0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626   -0.8736    1.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173   -1.0424    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7463   -0.7309   -0.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4892   -0.3732   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5066    0.0322   -1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.3631   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.7765   -1.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213    0.5245   -1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168    1.3618   -2.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.5618   -1.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.7530   -0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534    0.3273   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -0.4626    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806   -0.8312    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.3860    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940    0.4013    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4569    0.9302   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    2.3452   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036   -1.6254    2.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756   -1.7698    2.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -1.0341    0.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -0.1721    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4956   -1.0431    2.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3461   -1.3643    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.0984   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.5492   -1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.8723   -3.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    2.3577   -2.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    0.6238   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -0.6741    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    2.7336    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450   -1.3536    2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7209   -2.8415    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 26 18  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 23 36  1  0
 25 37  1  0
 25 38  1  0
M  END


  Mrv0541 05061305292D          

 26 31  0  0  0  0            999 V2000
    5.9868    3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464    3.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946    5.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    5.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    6.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514    4.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9183    4.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896    4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755    5.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    5.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    4.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    5.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323    4.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    4.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082    3.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4132    4.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5113    4.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    6.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003    3.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    4.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806    5.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  1  0  0  0  0
 23  7  1  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030756

> <DATABASE_NAME>
hmdb

> <SMILES>
OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2

> <INCHI_KEY>
HLEAVDSSZUIWQI-UHFFFAOYSA-N

> <FORMULA>
C19H12O7

> <MOLECULAR_WEIGHT>
352.2944

> <EXACT_MASS>
352.058302738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.33459463152187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
1.9097641453333332

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.026236562356312

> <JCHEM_PKA_STRONGEST_BASIC>
-3.045826688824046

> <JCHEM_POLAR_SURFACE_AREA>
87.36000000000001

> <JCHEM_REFRACTIVITY>
85.75219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12a-hydroxydolineone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030756
     RDKit          3D
13alpha-Hydroxydolineone
 38 43  0  0  0  0  0  0  0  0999 V2000
   -0.4194    0.6829    2.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856    0.6469    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253    0.2947    0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -0.1129    1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.4471    0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626   -0.8736    1.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173   -1.0424    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7463   -0.7309   -0.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4892   -0.3732   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5066    0.0322   -1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.3631   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.7765   -1.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213    0.5245   -1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168    1.3618   -2.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.5618   -1.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.7530   -0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534    0.3273   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -0.4626    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806   -0.8312    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.3860    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940    0.4013    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4569    0.9302   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    2.3452   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036   -1.6254    2.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756   -1.7698    2.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -1.0341    0.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -0.1721    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4956   -1.0431    2.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3461   -1.3643    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.0984   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.5492   -1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.8723   -3.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    2.3577   -2.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    0.6238   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -0.6741    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    2.7336    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450   -1.3536    2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7209   -2.8415    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 26 18  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 23 36  1  0
 25 37  1  0
 25 38  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      11.175   6.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.497   6.948   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.487   6.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.976   7.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.697   9.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.128  10.131   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.791  11.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.911   6.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.015   7.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.563   8.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.581   9.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.621   8.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.168   9.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.657  10.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.447   7.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.523   8.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.715  10.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.034   8.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.110   9.267   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.429   6.619   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.505   7.851   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.154   8.449   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.262  11.731   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.561   6.223   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.934   8.217   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.244  10.867   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   22                                                       
CONECT    3    9   10                                                       
CONECT    4   11   15                                                       
CONECT    5   12   13                                                       
CONECT    6   14   16                                                       
CONECT    7   17   23                                                       
CONECT    8   24   25                                                       
CONECT    9    1    3   12                                                  
CONECT   10    3   13   18                                                  
CONECT   11    4   14   19                                                  
CONECT   12    5    9   22                                                  
CONECT   13    5   10   26                                                  
CONECT   14    6   11   23                                                  
CONECT   15    4   16   24                                                  
CONECT   16    6   15   25                                                  
CONECT   17    7   19   26                                                  
CONECT   18   10   19   20                                                  
CONECT   19   11   17   18   21                                             
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22    2   12                                                       
CONECT   23    7   14                                                       
CONECT   24    8   15                                                       
CONECT   25    8   16                                                       
CONECT   26   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

COMPND    HMDB0030756
HETATM    1  O1  UNL     1      -0.419   0.683   2.135  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.586   0.647   0.885  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.925   0.295   0.445  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.919  -0.113   1.322  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.190  -0.447   0.907  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.363  -0.874   1.496  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.317  -1.042   0.511  1.00  0.00           C  
HETATM    8  O2  UNL     1      -5.746  -0.731  -0.627  1.00  0.00           O  
HETATM    9  C7  UNL     1      -4.489  -0.373  -0.440  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.507   0.032  -1.327  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.239   0.363  -0.894  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.241   0.776  -1.809  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.121   0.524  -1.511  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.017   1.362  -2.399  1.00  0.00           C  
HETATM   15  O4  UNL     1       2.305   1.562  -1.824  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.761   0.753  -0.762  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.053   0.327  -0.640  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.404  -0.463   0.435  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.481  -0.831   1.386  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.171  -0.386   1.241  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.794   0.401   0.182  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.457   0.930  -0.081  1.00  0.00           C  
HETATM   23  O5  UNL     1       0.591   2.345  -0.137  1.00  0.00           O  
HETATM   24  O6  UNL     1       4.104  -1.625   2.355  1.00  0.00           O  
HETATM   25  C19 UNL     1       5.476  -1.770   2.007  1.00  0.00           C  
HETATM   26  O7  UNL     1       5.610  -1.034   0.818  1.00  0.00           O  
HETATM   27  H1  UNL     1      -2.693  -0.172   2.369  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.496  -1.043   2.555  1.00  0.00           H  
HETATM   29  H3  UNL     1      -7.346  -1.364   0.598  1.00  0.00           H  
HETATM   30  H4  UNL     1      -3.719   0.098  -2.395  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.379  -0.549  -1.601  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.130   0.872  -3.400  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.559   2.358  -2.576  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.786   0.624  -1.402  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.436  -0.674   1.986  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.307   2.734   0.024  1.00  0.00           H  
HETATM   37  H11 UNL     1       6.145  -1.354   2.791  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.721  -2.842   1.779  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    4   11
CONECT    4    5   27
CONECT    5    6    9    9
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9
CONECT    9   10
CONECT   10   11   11   30
CONECT   11   12
CONECT   12   13
CONECT   13   14   22   31
CONECT   14   15   32   33
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   34
CONECT   18   19   19   26
CONECT   19   20   24
CONECT   20   21   21   35
CONECT   21   22
CONECT   22   23
CONECT   23   36
CONECT   24   25
CONECT   25   26   37   38
END

HMDB0030756
     RDKit          3D
13alpha-Hydroxydolineone
 38 43  0  0  0  0  0  0  0  0999 V2000
   -0.4194    0.6829    2.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856    0.6469    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253    0.2947    0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -0.1129    1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.4471    0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626   -0.8736    1.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173   -1.0424    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7463   -0.7309   -0.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4892   -0.3732   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5066    0.0322   -1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.3631   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.7765   -1.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213    0.5245   -1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168    1.3618   -2.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.5618   -1.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.7530   -0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534    0.3273   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -0.4626    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806   -0.8312    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.3860    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940    0.4013    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4569    0.9302   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    2.3452   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036   -1.6254    2.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756   -1.7698    2.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -1.0341    0.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -0.1721    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4956   -1.0431    2.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3461   -1.3643    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.0984   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.5492   -1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.8723   -3.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    2.3577   -2.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    0.6238   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -0.6741    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    2.7336    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450   -1.3536    2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7209   -2.8415    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 26 18  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
 23 36  1  0
 25 37  1  0
 25 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13a-Hydroxydolineone	Generator
13Α-hydroxydolineone	Generator

Chemical Formula

C₁₉H₁₂O₇

Average Molecular Weight

352.2944

Monoisotopic Molecular Weight

352.058302738

IUPAC Name

1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

Traditional Name

12a-hydroxydolineone

CAS Registry Number

28617-71-2

SMILES

OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O

InChI Identifier

InChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2

InChI Key

HLEAVDSSZUIWQI-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
Isoflavanone
Isoflavan
Furanochromone
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Tertiary alcohol
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060033 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030756)
Cytoplasm (HMDB: HMDB0030756)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030756)

Source

Endogenous

Endogenous (HMDB: HMDB0030756)

Plant

Plant (HMDB: HMDB0030756)
Fabaceae (HMDB: HMDB0030756)

Exogenous

Food

Food (HMDB: HMDB0030756)

Pulse

Pulses (FooDB: FOOD00867)

Vegetable

Root vegetable

Jicama (FooDB: FOOD00509)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 - 195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	432.6 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	0.5 g/L	ALOGPS
logP	2.08	ALOGPS
logP	1.91	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	87.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.75 m³·mol⁻¹	ChemAxon
Polarizability	34.33 Å³	ChemAxon
Number of Rings	6	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]+	176.798	31661259
DarkChem	[M-H]-	178.691	31661259
DeepCCS	[M-2H]-	216.928	30932474
DeepCCS	[M+Na]+	192.156	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.3	32859911
AllCCS	[M+NH4]+	184.6	32859911
AllCCS	[M+Na]+	185.4	32859911
AllCCS	[M-H]-	184.3	32859911
AllCCS	[M+Na-2H]-	183.2	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13alpha-Hydroxydolineone	OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O	4790.6	Standard polar	33892256
13alpha-Hydroxydolineone	OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O	3002.9	Standard non polar	33892256
13alpha-Hydroxydolineone	OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O	3106.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13alpha-Hydroxydolineone,1TMS,isomer #1	C[Si](C)(C)OC12C(=O)C3=CC4=C(C=C3OC1COC1=CC3=C(C=C12)OCO3)OC=C4	3262.7	Semi standard non polar	33892256
13alpha-Hydroxydolineone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12C(=O)C3=CC4=C(C=C3OC1COC1=CC3=C(C=C12)OCO3)OC=C4	3533.1	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 - 13alpha-Hydroxydolineone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-2913000000-506dee24db7b8cf3a618	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13alpha-Hydroxydolineone GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-9343200000-96d8036ba9a77c71c661	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13alpha-Hydroxydolineone 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 - 13alpha-Hydroxydolineone 10V, Positive-QTOF	splash10-0udi-0009000000-586b0b4a691c1edcb5c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Positive-QTOF	splash10-0w29-0619000000-7dcbda7eea674461b590	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Positive-QTOF	splash10-03di-1900000000-ebb97846d21913823d47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Negative-QTOF	splash10-0udi-0109000000-128203575629f8eed5f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Negative-QTOF	splash10-0udi-0409000000-4a49f6ba37c665e7bd7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Negative-QTOF	splash10-0a4i-1900000000-ba731628889bb1115477	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Positive-QTOF	splash10-0udi-0009000000-6b09288367f287c3aa7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Positive-QTOF	splash10-0udi-0009000000-75ec90160a6d1d79cb22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Positive-QTOF	splash10-0ika-0922000000-46a80340180660ae5945	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 10V, Negative-QTOF	splash10-0udi-0009000000-fbaae7d8d0a33f870dc0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 20V, Negative-QTOF	splash10-0udi-0009000000-9850b65af18c86bc4c3e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13alpha-Hydroxydolineone 40V, Negative-QTOF	splash10-0f7c-0917000000-8afcc2a79ad23f675c7f	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002688

KNApSAcK ID

C00009582

Chemspider ID

24842945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13885696

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

13alpha-Hydroxydolineone → 3,4,5-trihydroxy-6-({24-oxo-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-1-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 13alpha-Hydroxydolineone (HMDB0030756)

MOL for HMDB0030756 (13alpha-Hydroxydolineone)

3D MOL for HMDB0030756 (13alpha-Hydroxydolineone)

3D SDF for HMDB0030756 (13alpha-Hydroxydolineone)

3D-SDF for HMDB0030756 (13alpha-Hydroxydolineone)

PDB for HMDB0030756 (13alpha-Hydroxydolineone)

3D PDB for HMDB0030756 (13alpha-Hydroxydolineone)

SMILES for HMDB0030756 (13alpha-Hydroxydolineone)

INCHI for HMDB0030756 (13alpha-Hydroxydolineone)

Structure for HMDB0030756 (13alpha-Hydroxydolineone)

3D Structure for HMDB0030756 (13alpha-Hydroxydolineone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions