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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:48:53 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034039

Secondary Accession Numbers

HMDB34039

Metabolite Identification

Common Name

Dolineone

Description

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

Structure

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


  Mrv0541 05061307312D          

 25 30  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
    1.9183    4.8658    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
    5.6896    4.6003    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
    4.3755    5.1617    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
    2.7374    4.9645    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
    2.9082    3.5458    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  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  2  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
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 16  1  0  0  0  0
 25 14  1  0  0  0  0
 25 17  1  0  0  0  0
M  END

HMDB0034039
     RDKit          3D
Dolineone
 37 42  0  0  0  0  0  0  0  0999 V2000
    0.1745    1.7069    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.5304    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381    0.1633    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015    1.1211    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.7289    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.4038    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121    0.4669    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -0.6987    0.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844   -0.6027    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776   -1.5129    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2327   -1.1670    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.1310   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -1.6513   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -2.7564   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.1334   -1.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.9766   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917   -0.5636   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.5617   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    1.3016    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555    0.9247    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431   -0.2300    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -0.6204    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    2.4081    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4912    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7514    1.1871   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    2.1480    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    2.4751    1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4736    0.7115    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -2.5720   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -1.1598   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -3.3371    0.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -3.4275   -1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.1775   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    1.5272    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -1.0637    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    2.7153    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4210    3.2086   -0.4657 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
 19 23  1  0
 23 24  1  0
 24 25  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 25 18  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 22 35  1  0
 24 36  1  0
 24 37  1  0
M  END


  Mrv0541 05061307312D          

 25 30  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
    1.9183    4.8658    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
    5.6896    4.6003    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
    4.3755    5.1617    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
    2.7374    4.9645    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
    2.9082    3.5458    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  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  2  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
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 16  1  0  0  0  0
 25 14  1  0  0  0  0
 25 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034039

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O6/c20-19-11-3-9-1-2-21-12(9)5-14(11)25-17-7-22-13-6-16-15(23-8-24-16)4-10(13)18(17)19/h1-6,17-18H,7-8H2

> <INCHI_KEY>
RAJDDCCSNZAPCH-UHFFFAOYSA-N

> <FORMULA>
C19H12O6

> <MOLECULAR_WEIGHT>
336.295

> <EXACT_MASS>
336.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.566620389959624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
3.07

> <JCHEM_LOGP>
2.5012818083333332

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.42933693141694

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0298270169827544

> <JCHEM_POLAR_SURFACE_AREA>
67.13000000000001

> <JCHEM_REFRACTIVITY>
84.50619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dolineone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034039
     RDKit          3D
Dolineone
 37 42  0  0  0  0  0  0  0  0999 V2000
    0.1745    1.7069    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.5304    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381    0.1633    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015    1.1211    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.7289    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.4038    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121    0.4669    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -0.6987    0.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844   -0.6027    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776   -1.5129    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2327   -1.1670    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.1310   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -1.6513   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -2.7564   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.1334   -1.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.9766   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917   -0.5636   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.5617   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    1.3016    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555    0.9247    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431   -0.2300    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -0.6204    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    2.4081    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4912    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7514    1.1871   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    2.1480    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    2.4751    1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4736    0.7115    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -2.5720   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -1.1598   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -3.3371    0.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -3.4275   -1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.1775   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    1.5272    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -1.0637    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    2.7153    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4210    3.2086   -0.4657 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
 19 23  1  0
 23 24  1  0
 24 25  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 25 18  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 22 35  1  0
 24 36  1  0
 24 37  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       3.581   9.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.563   8.219   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       2.657  10.315   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.168   9.635   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       5.110   9.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.034   8.035   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      12.154   8.449   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.262  11.731   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.561   6.223   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.934   8.217   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.244  10.867   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   21                                                       
CONECT    3    9   11                                                       
CONECT    4   10   15                                                       
CONECT    5   12   14                                                       
CONECT    6   13   16                                                       
CONECT    7   17   22                                                       
CONECT    8   23   24                                                       
CONECT    9    1    3   12                                                  
CONECT   10    4   13   18                                                  
CONECT   11    3   14   19                                                  
CONECT   12    5    9   21                                                  
CONECT   13    6   10   22                                                  
CONECT   14    5   11   25                                                  
CONECT   15    4   16   23                                                  
CONECT   16    6   15   24                                                  
CONECT   17    7   18   25                                                  
CONECT   18   10   17   19                                                  
CONECT   19   11   18   20                                                  
CONECT   20   19                                                            
CONECT   21    2   12                                                       
CONECT   22    7   13                                                       
CONECT   23    8   15                                                       
CONECT   24    8   16                                                       
CONECT   25   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

COMPND    HMDB0034039
HETATM    1  O1  UNL     1       0.174   1.707   0.119  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.510   0.530   0.288  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.938   0.163   0.332  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.901   1.121   0.581  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.229   0.729   0.613  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.408   1.404   0.828  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.412   0.467   0.735  1.00  0.00           C  
HETATM    8  O2  UNL     1       5.885  -0.699   0.482  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.584  -0.603   0.398  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.578  -1.513   0.154  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.233  -1.167   0.112  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.260  -2.131  -0.139  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.016  -1.651  -0.524  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.011  -2.756  -0.725  1.00  0.00           C  
HETATM   15  O4  UNL     1      -2.200  -2.133  -1.185  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.677  -0.977  -0.563  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.992  -0.564  -0.741  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.508   0.562  -0.154  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.664   1.302   0.646  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.356   0.925   0.846  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.843  -0.230   0.237  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.439  -0.620   0.461  1.00  0.00           C  
HETATM   23  O5  UNL     1      -4.378   2.408   1.151  1.00  0.00           O  
HETATM   24  C19 UNL     1      -5.551   2.491   0.366  1.00  0.00           C  
HETATM   25  O6  UNL     1      -5.751   1.187  -0.161  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.610   2.148   0.746  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.497   2.475   1.030  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.474   0.712   0.862  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.819  -2.572  -0.020  1.00  0.00           H  
HETATM   30  H5  UNL     1       0.139  -1.160  -1.528  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.163  -3.337   0.201  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.608  -3.427  -1.512  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.609  -1.177  -1.375  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.696   1.527   1.489  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.322  -1.064   1.480  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.448   2.715   0.986  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.421   3.209  -0.466  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    4   11
CONECT    4    5   26
CONECT    5    6    9    9
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9
CONECT    9   10
CONECT   10   11   11   29
CONECT   11   12
CONECT   12   13
CONECT   13   14   22   30
CONECT   14   15   31   32
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   33
CONECT   18   19   19   25
CONECT   19   20   23
CONECT   20   21   21   34
CONECT   21   22
CONECT   22   35
CONECT   23   24
CONECT   24   25   36   37
END

HMDB0034039
     RDKit          3D
Dolineone
 37 42  0  0  0  0  0  0  0  0999 V2000
    0.1745    1.7069    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.5304    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381    0.1633    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015    1.1211    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.7289    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.4038    0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121    0.4669    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -0.6987    0.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844   -0.6027    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776   -1.5129    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2327   -1.1670    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.1310   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -1.6513   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -2.7564   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.1334   -1.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.9766   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917   -0.5636   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.5617   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    1.3016    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555    0.9247    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431   -0.2300    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -0.6204    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    2.4081    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4912    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7514    1.1871   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    2.1480    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    2.4751    1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4736    0.7115    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -2.5720   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393   -1.1598   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -3.3371    0.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -3.4275   -1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.1775   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962    1.5272    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -1.0637    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    2.7153    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4210    3.2086   -0.4657 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
 19 23  1  0
 23 24  1  0
 24 25  1  0
 22  2  1  0
 11  3  1  0
 22 13  1  0
  9  5  2  0
 21 16  1  0
 25 18  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 22 35  1  0
 24 36  1  0
 24 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Dolineone	HMDB
6a,13a-dihydro-1,3-dioxolo[6,7][1]benzopyrano[3,4-b]furo[3,2-g][1]Benzopyran-13(6H)-one, 9ci	HMDB
Dolichone	HMDB

Chemical Formula

C₁₉H₁₂O₆

Average Molecular Weight

336.295

Monoisotopic Molecular Weight

336.063388116

IUPAC Name

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

dolineone

CAS Registry Number

10065-28-8

SMILES

O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2

InChI Identifier

InChI=1S/C19H12O6/c20-19-11-3-9-1-2-21-12(9)5-14(11)25-17-7-22-13-6-16-15(23-8-24-16)4-10(13)18(17)19/h1-6,17-18H,7-8H2

InChI Key

RAJDDCCSNZAPCH-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
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060008 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034039)
Cell membrane (HMDB: HMDB0034039)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034039)

Source

Exogenous

Exogenous (HMDB: HMDB0034039)

Food

Food (HMDB: HMDB0034039)

Vegetable

Root vegetable

Jicama (FooDB: FOOD00509)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0034039)
Fabaceae (HMDB: HMDB0034039)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034039)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	233 - 235 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8.7 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	0.16 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	67.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.51 m³·mol⁻¹	ChemAxon
Polarizability	33.57 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]+	174.375	31661259
DarkChem	[M-H]-	175.557	31661259
DeepCCS	[M-2H]-	209.161	30932474
DeepCCS	[M+Na]+	184.388	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	181.8	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	181.7	32859911
AllCCS	[M+Na-2H]-	180.5	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.34 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0255 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2326.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	471.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	254.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	634.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	714.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1335.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	510.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1776.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	475.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	465.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	494.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	110.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dolineone	O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2	4690.0	Standard polar	33892256
Dolineone	O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2	2937.3	Standard non polar	33892256
Dolineone	O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2	3090.1	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 - Dolineone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-2819000000-edb336889e511cfef035	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dolineone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dolineone 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 - Dolineone 10V, Positive-QTOF	splash10-000i-0009000000-8b33061978fbf6a44600	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 20V, Positive-QTOF	splash10-00kr-0329000000-bf271617ade8e362283b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 40V, Positive-QTOF	splash10-03di-0921000000-be65b7425e7f76a39b64	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 10V, Negative-QTOF	splash10-000i-0009000000-2557d6ca9a6e4c5b8bfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 20V, Negative-QTOF	splash10-000i-0019000000-964f57b779ee0766ead5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 40V, Negative-QTOF	splash10-0a4j-0911000000-33c608b6d67401bdab98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 10V, Positive-QTOF	splash10-000i-0009000000-a487dc1a344a66353635	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 20V, Positive-QTOF	splash10-000i-0009000000-a487dc1a344a66353635	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 40V, Positive-QTOF	splash10-0kbk-0915000000-462d3f76132742d32941	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 10V, Negative-QTOF	splash10-000i-0009000000-cf75db3fcf76086bc0a2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 20V, Negative-QTOF	splash10-000i-0009000000-25a65af29ec4c92f7741	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolineone 40V, Negative-QTOF	splash10-052r-0209000000-5209610c956607dbb456	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB012281

KNApSAcK ID

C00009568

Chemspider ID

4475907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316959

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840001

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.. .

Showing metabocard for Dolineone (HMDB0034039)

MOL for HMDB0034039 (Dolineone)

3D MOL for HMDB0034039 (Dolineone)

3D SDF for HMDB0034039 (Dolineone)

3D-SDF for HMDB0034039 (Dolineone)

PDB for HMDB0034039 (Dolineone)

3D PDB for HMDB0034039 (Dolineone)

SMILES for HMDB0034039 (Dolineone)

INCHI for HMDB0034039 (Dolineone)

Structure for HMDB0034039 (Dolineone)

3D Structure for HMDB0034039 (Dolineone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra