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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:56:25 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034145

Secondary Accession Numbers

HMDB34145

Metabolite Identification

Common Name

(-)-cis-Rotenolone

Description

(-)-cis-Rotenolone 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 (-)-cis-Rotenolone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make (-)-cis-rotenolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-cis-Rotenolone.

Structure

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

  Mrv0541 02241220202D          

 31 35  0  0  0  0            999 V2000
   -1.9049   -1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.0697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2370   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937    1.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    2.2007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1913    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348   -1.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370   -1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.7196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 21  1  0  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  4 30  1  6  0  0  0
  5  6  1  0  0  0  0
  5 29  2  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 25  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 16 31  1  6  0  0  0
M  END

HMDB0034145
     RDKit          3D
(-)-cis-Rotenolone
 52 56  0  0  0  0  0  0  0  0999 V2000
   -6.4410   -1.1151    1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3705    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528    0.9628    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2541   -0.8967   -0.5645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0761    0.0238   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.7380   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -2.0041    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -2.8585    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.4637    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -1.1875    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.3201    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.9514   -0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.1333   -0.6960 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3358    0.4046   -1.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -0.4067   -1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.0005   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.1082   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    0.3322   -1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3025    0.2320   -1.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -0.3370   -2.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8056    0.8848    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    1.3272    0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203    1.9009    2.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    1.0075    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694    0.5614   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673    0.6579    0.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9990    1.4864    1.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448   -0.7213    0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -1.5412    1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -2.1280   -0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1238   -0.7590    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -2.0746    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    1.2122   -0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8645    0.8757    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    1.7530    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.9905   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451    0.1534   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    0.9818   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976   -3.8711    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.1402    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077    2.2277   -0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4936    1.1589   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.2130   -2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835   -0.5437   -2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5998   -0.3891   -3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538    0.2616   -3.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -1.3755   -2.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5959    2.4799    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5808    1.0911    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    2.6278    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.4323    1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7778    2.4322    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  2  0
  7 30  1  0
 30  4  1  0
 11  6  1  0
 26 13  1  0
 28 10  1  0
 25 16  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  6
 14 42  1  0
 14 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
M  END

  Mrv0541 02241220202D          

 31 35  0  0  0  0            999 V2000
   -1.9049   -1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.0697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2370   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937    1.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    2.2007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1913    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348   -1.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370   -1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.7196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 21  1  0  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  4 30  1  6  0  0  0
  5  6  1  0  0  0  0
  5 29  2  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 25  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 16 31  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0034145

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

> <INCHI_KEY>
JFVKWCYZKMUTLH-AYPBNUJASA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.4166

> <EXACT_MASS>
410.136553058

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.79904288951134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.728660151333333

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.075276263311958

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2046903864344705

> <JCHEM_POLAR_SURFACE_AREA>
83.45

> <JCHEM_REFRACTIVITY>
106.95830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rotenolone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034145
     RDKit          3D
(-)-cis-Rotenolone
 52 56  0  0  0  0  0  0  0  0999 V2000
   -6.4410   -1.1151    1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3705    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528    0.9628    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2541   -0.8967   -0.5645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0761    0.0238   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.7380   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -2.0041    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -2.8585    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.4637    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -1.1875    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.3201    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.9514   -0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.1333   -0.6960 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3358    0.4046   -1.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -0.4067   -1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.0005   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.1082   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    0.3322   -1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3025    0.2320   -1.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -0.3370   -2.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8056    0.8848    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    1.3272    0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203    1.9009    2.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    1.0075    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694    0.5614   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673    0.6579    0.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9990    1.4864    1.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448   -0.7213    0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -1.5412    1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -2.1280   -0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1238   -0.7590    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -2.0746    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    1.2122   -0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8645    0.8757    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    1.7530    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.9905   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451    0.1534   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    0.9818   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976   -3.8711    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.1402    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077    2.2277   -0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4936    1.1589   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.2130   -2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835   -0.5437   -2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5998   -0.3891   -3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538    0.2616   -3.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -1.3755   -2.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5959    2.4799    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5808    1.0911    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    2.6278    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.4323    1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7778    2.4322    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  2  0
  7 30  1  0
 30  4  1  0
 11  6  1  0
 26 13  1  0
 28 10  1  0
 25 16  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  6
 14 42  1  0
 14 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.556  -2.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.224  -2.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.224  -0.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.889   0.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.442  -0.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.777   0.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.112  -0.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.443   0.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.443   1.670   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.588   2.702   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.962   4.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.430   3.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.112   2.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.777   1.670   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.442   2.440   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.889   1.670   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.224   2.440   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.556   1.670   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.556   0.130   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.890  -0.640   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.890  -2.180   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.225  -2.950   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.557  -2.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.272   5.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.732   5.440   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.962   6.775   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.556  -4.490   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.890  -5.259   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.442  -2.180   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.889  -1.410   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.889   3.210   0.000  0.00  0.00           H+0
CONECT    1    2   21   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   16   30                                             
CONECT    5    4    6   29                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14    6   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    4   15   17   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19    3   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    1   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   11   24   26                                                  
CONECT   26   25                                                            
CONECT   27    1   28                                                       
CONECT   28   27                                                            
CONECT   29    5                                                            
CONECT   30    4                                                            
CONECT   31   16                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0034145
HETATM    1  C1  UNL     1      -6.441  -1.115   1.534  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.200  -0.370   0.461  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.853   0.963   0.273  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.254  -0.897  -0.564  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.076   0.024  -0.748  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.949  -0.738  -0.171  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.364  -2.004   0.167  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.436  -2.859   0.724  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.122  -2.464   0.942  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.731  -1.188   0.594  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.629  -0.320   0.040  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.211   0.951  -0.299  1.00  0.00           O  
HETATM   13  C12 UNL     1       0.157   1.133  -0.696  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.336   0.405  -1.977  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.514  -0.407  -1.995  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.656  -0.000  -1.327  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.925  -0.108  -1.802  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.012   0.332  -1.050  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.303   0.232  -1.513  1.00  0.00           O  
HETATM   20  C17 UNL     1       6.515  -0.337  -2.791  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.806   0.885   0.191  1.00  0.00           C  
HETATM   22  O4  UNL     1       5.895   1.327   0.947  1.00  0.00           O  
HETATM   23  C19 UNL     1       5.720   1.901   2.227  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.536   1.007   0.699  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.469   0.561  -0.069  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.067   0.658   0.410  1.00  0.00           C  
HETATM   27  O5  UNL     1       0.999   1.486   1.512  1.00  0.00           O  
HETATM   28  C23 UNL     1       0.645  -0.721   0.805  1.00  0.00           C  
HETATM   29  O6  UNL     1       1.441  -1.541   1.332  1.00  0.00           O  
HETATM   30  O7  UNL     1      -4.704  -2.128  -0.154  1.00  0.00           O  
HETATM   31  H1  UNL     1      -7.124  -0.759   2.296  1.00  0.00           H  
HETATM   32  H2  UNL     1      -5.968  -2.075   1.665  1.00  0.00           H  
HETATM   33  H3  UNL     1      -7.013   1.212  -0.783  1.00  0.00           H  
HETATM   34  H4  UNL     1      -7.864   0.876   0.764  1.00  0.00           H  
HETATM   35  H5  UNL     1      -6.319   1.753   0.838  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.778  -0.990  -1.556  1.00  0.00           H  
HETATM   37  H7  UNL     1      -3.845   0.153  -1.838  1.00  0.00           H  
HETATM   38  H8  UNL     1      -4.176   0.982  -0.229  1.00  0.00           H  
HETATM   39  H9  UNL     1      -2.698  -3.871   1.013  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.384  -3.140   1.384  1.00  0.00           H  
HETATM   41  H11 UNL     1       0.308   2.228  -0.800  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.494   1.159  -2.794  1.00  0.00           H  
HETATM   43  H13 UNL     1      -0.539  -0.213  -2.264  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.084  -0.544  -2.778  1.00  0.00           H  
HETATM   45  H15 UNL     1       7.600  -0.389  -3.034  1.00  0.00           H  
HETATM   46  H16 UNL     1       5.954   0.262  -3.546  1.00  0.00           H  
HETATM   47  H17 UNL     1       6.113  -1.376  -2.866  1.00  0.00           H  
HETATM   48  H18 UNL     1       6.596   2.480   2.554  1.00  0.00           H  
HETATM   49  H19 UNL     1       5.581   1.091   2.978  1.00  0.00           H  
HETATM   50  H20 UNL     1       4.861   2.628   2.247  1.00  0.00           H  
HETATM   51  H21 UNL     1       3.317   1.432   1.665  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.778   2.432   1.263  1.00  0.00           H  
CONECT    1    2    2   31   32
CONECT    2    3    4
CONECT    3   33   34   35
CONECT    4    5   30   36
CONECT    5    6   37   38
CONECT    6    7    7   11
CONECT    7    8   30
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   11   28
CONECT   11   12
CONECT   12   13
CONECT   13   14   26   41
CONECT   14   15   42   43
CONECT   15   16
CONECT   16   17   17   25
CONECT   17   18   44
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   45   46   47
CONECT   21   22   24
CONECT   22   23
CONECT   23   48   49   50
CONECT   24   25   25   51
CONECT   25   26
CONECT   26   27   28
CONECT   27   52
CONECT   28   29   29
END

HMDB0034145
     RDKit          3D
(-)-cis-Rotenolone
 52 56  0  0  0  0  0  0  0  0999 V2000
   -6.4410   -1.1151    1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3705    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8528    0.9628    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2541   -0.8967   -0.5645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0761    0.0238   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -0.7380   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -2.0041    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -2.8585    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.4637    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -1.1875    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.3201    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.9514   -0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.1333   -0.6960 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3358    0.4046   -1.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -0.4067   -1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.0005   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.1082   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    0.3322   -1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3025    0.2320   -1.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -0.3370   -2.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8056    0.8848    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    1.3272    0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203    1.9009    2.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    1.0075    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694    0.5614   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673    0.6579    0.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9990    1.4864    1.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448   -0.7213    0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -1.5412    1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -2.1280   -0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1238   -0.7590    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -2.0746    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    1.2122   -0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8645    0.8757    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    1.7530    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.9905   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451    0.1534   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    0.9818   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976   -3.8711    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.1402    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077    2.2277   -0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4936    1.1589   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.2130   -2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835   -0.5437   -2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5998   -0.3891   -3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538    0.2616   -3.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -1.3755   -2.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5959    2.4799    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5808    1.0911    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    2.6278    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    1.4323    1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7778    2.4322    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  2  0
  7 30  1  0
 30  4  1  0
 11  6  1  0
 26 13  1  0
 28 10  1  0
 25 16  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  6
 14 42  1  0
 14 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-cis-12a-Hydroxyrotenone	HMDB
1,2,12,12a-tetrahydro-6a-Hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	HMDB
12-Hydroxyrotenone	HMDB
12alpha-Hydroxyrotenone	HMDB
6a-beta,12a-beta-Rotenolone	HMDB
6Ab,12ab-rotenolone	HMDB
Rotenalone	HMDB
Rotenolon I	HMDB
Rotenolone	HMDB
Rotenolone I	HMDB
6 alpha(beta),12 alpha(beta)-Rotenolone	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6abeta,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12abeta))-isomer	MeSH

Chemical Formula

C₂₃H₂₂O₇

Average Molecular Weight

410.4166

Monoisotopic Molecular Weight

410.136553058

IUPAC Name

(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one

Traditional Name

rotenolone

CAS Registry Number

509-96-6

SMILES

[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C

InChI Identifier

InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

InChI Key

JFVKWCYZKMUTLH-AYPBNUJASA-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
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Chromone
1-benzopyran
Chromane
Benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:68051 )
rotenones (C10464 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034145)
Cytoplasm (HMDB: HMDB0034145)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034145)

Source

Exogenous

Exogenous (HMDB: HMDB0034145)

Food

Food (HMDB: HMDB0034145)

Vegetable

Root vegetable

Jicama (FooDB: FOOD00509)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0034145)
Fabaceae (HMDB: HMDB0034145)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034145)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	91 - 92 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.73	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.96 m³·mol⁻¹	ChemAxon
Polarizability	42.8 Å³	ChemAxon
Number of Rings	5	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]+	195.466	31661259
DarkChem	[M-H]-	196.181	31661259
DeepCCS	[M-2H]-	227.649	30932474
DeepCCS	[M+Na]+	203.073	30932474
AllCCS	[M+H]+	199.5	32859911
AllCCS	[M+H-H2O]+	196.8	32859911
AllCCS	[M+NH4]+	202.0	32859911
AllCCS	[M+Na]+	202.7	32859911
AllCCS	[M-H]-	202.1	32859911
AllCCS	[M+Na-2H]-	202.2	32859911
AllCCS	[M+HCOO]-	202.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-cis-Rotenolone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	4792.1	Standard polar	33892256
(-)-cis-Rotenolone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	3259.5	Standard non polar	33892256
(-)-cis-Rotenolone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	3212.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-cis-Rotenolone,1TMS,isomer #1	C=C(C)[C@H]1CC2=C(C=CC3=C2O[C@@H]2COC4=CC(OC)=C(OC)C=C4[C@]2(O[Si](C)(C)C)C3=O)O1	3260.4	Semi standard non polar	33892256
(-)-cis-Rotenolone,1TBDMS,isomer #1	C=C(C)[C@H]1CC2=C(C=CC3=C2O[C@@H]2COC4=CC(OC)=C(OC)C=C4[C@]2(O[Si](C)(C)C(C)(C)C)C3=O)O1	3472.9	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 - (-)-cis-Rotenolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udj-2898000000-a911918046b993e78796	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-cis-Rotenolone GC-MS (1 TMS) - 70eV, Positive	splash10-0v4i-9420700000-d42a2e5be951b642755e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-cis-Rotenolone 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 - (-)-cis-Rotenolone 10V, Positive-QTOF	splash10-03di-1223900000-9a1f17cd964abaa81aa8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 20V, Positive-QTOF	splash10-0w29-2394300000-b8d33d58c295207f77a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 40V, Positive-QTOF	splash10-0udi-2930000000-7ebdad6df07b04059cf4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 10V, Negative-QTOF	splash10-0a4i-0011900000-068963a903131042e2de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 20V, Negative-QTOF	splash10-0a4i-0059600000-b085e22dff915ed213c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 40V, Negative-QTOF	splash10-0udr-1933000000-acb18ae95eb8c0f59fb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 10V, Negative-QTOF	splash10-0a4i-0000900000-13ca06aa040c9821ae69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 20V, Negative-QTOF	splash10-0a4i-0325900000-33ff0fbbe9523120bd61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 40V, Negative-QTOF	splash10-0a4i-1869100000-793032f9edca87024cfd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 10V, Positive-QTOF	splash10-03di-0000900000-cc474c0f71581fe9b76f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 20V, Positive-QTOF	splash10-03di-0115900000-866e3635b32607356e9c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-cis-Rotenolone 40V, Positive-QTOF	splash10-0zi0-3395000000-409148100e6d88cb50cd	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for (-)-cis-Rotenolone (HMDB0034145)

MOL for HMDB0034145 ((-)-cis-Rotenolone)

3D MOL for HMDB0034145 ((-)-cis-Rotenolone)

3D SDF for HMDB0034145 ((-)-cis-Rotenolone)

3D-SDF for HMDB0034145 ((-)-cis-Rotenolone)

PDB for HMDB0034145 ((-)-cis-Rotenolone)

3D PDB for HMDB0034145 ((-)-cis-Rotenolone)

SMILES for HMDB0034145 ((-)-cis-Rotenolone)

INCHI for HMDB0034145 ((-)-cis-Rotenolone)

Structure for HMDB0034145 ((-)-cis-Rotenolone)

3D Structure for HMDB0034145 ((-)-cis-Rotenolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra