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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:16:54 UTC

Update Date

2022-03-07 02:54:06 UTC

HMDB ID

HMDB0034436

Secondary Accession Numbers

HMDB34436

Metabolite Identification

Common Name

Rotenone

Description

Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease.

Structure

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


  Mrv1652305271900282D          

 31 35  0  0  1  0            999 V2000
    3.9940    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    2.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8800    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    3.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9940    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    0.3854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5651    1.2104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2795    1.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -1.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -1.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -2.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -2.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.4396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    2.0354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 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
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
M  END

HMDB0034436
     RDKit          3D
Rotenone
 51 55  0  0  0  0  0  0  0  0999 V2000
    6.5014   -1.7100    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.4512    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5754    0.4115    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.1345    0.0340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9354   -0.8128    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1946    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279    1.4307    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881    2.4857    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.3457    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    1.0856    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -0.0044    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -1.2335    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.2301   -0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3185   -0.6440   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.3038   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.1029   -1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7804    0.2932   -1.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9947    0.0584   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788    0.2289   -1.9612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    0.6453   -3.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -0.3476    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -0.5653    0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3115   -0.9828    1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622   -0.5350    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6502   -0.3073    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -0.4754    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7693    0.8712    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8785    1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    1.2962    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5374   -2.0708    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -2.3554    0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.5964   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3661    1.3802    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -0.0386    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    0.4580   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.3131    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -1.5013   -0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549    3.4632    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    3.1629    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507   -2.2959   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -0.1353   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -1.4636   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329    0.6095   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550    1.5820   -3.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6397   -0.1007   -3.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1640    0.8573   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3687    2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9307   -2.0342    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3582   -1.0015    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8552   -0.8473    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -1.0505    1.7338 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  0
 27 28  2  0
  7 29  1  0
 29  4  1  0
 11  6  1  0
 26 13  1  0
 27 10  1  0
 25 16  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
 13 40  1  6
 14 41  1  0
 14 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 26 51  1  1
M  END


  Mrv1652305271900282D          

 31 35  0  0  1  0            999 V2000
    3.9940    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    2.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8800    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    3.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9940    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    0.3854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5651    1.2104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2795    1.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -1.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -1.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -2.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -2.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.4396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    2.0354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 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
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0034436

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

> <INCHI_KEY>
JUVIOZPCNVVQFO-HBGVWJBISA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.4172

> <EXACT_MASS>
394.141638436

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.07171729217053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
3.320177814333334

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.803545634313098

> <JCHEM_PKA_STRONGEST_BASIC>
-4.19837863212729

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
105.7123

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034436
     RDKit          3D
Rotenone
 51 55  0  0  0  0  0  0  0  0999 V2000
    6.5014   -1.7100    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.4512    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5754    0.4115    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.1345    0.0340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9354   -0.8128    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1946    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279    1.4307    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881    2.4857    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.3457    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    1.0856    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -0.0044    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -1.2335    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.2301   -0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3185   -0.6440   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.3038   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.1029   -1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7804    0.2932   -1.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9947    0.0584   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788    0.2289   -1.9612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    0.6453   -3.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -0.3476    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -0.5653    0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3115   -0.9828    1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622   -0.5350    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6502   -0.3073    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -0.4754    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7693    0.8712    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8785    1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    1.2962    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5374   -2.0708    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -2.3554    0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.5964   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3661    1.3802    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -0.0386    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    0.4580   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.3131    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -1.5013   -0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549    3.4632    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    3.1629    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507   -2.2959   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -0.1353   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -1.4636   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329    0.6095   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550    1.5820   -3.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6397   -0.1007   -3.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1640    0.8573   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3687    2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9307   -2.0342    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3582   -1.0015    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8552   -0.8473    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -1.0505    1.7338 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  0
 27 28  2  0
  7 29  1  0
 29  4  1  0
 11  6  1  0
 26 13  1  0
 27 10  1  0
 25 16  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
 13 40  1  6
 14 41  1  0
 14 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 26 51  1  1
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       7.455   2.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.789   3.029   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.123   2.259   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.267   3.290   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.641   4.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.109   4.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.411   6.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.951   6.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.641   7.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.123   0.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.789  -0.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.455   0.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.122  -0.051   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.122  -1.591   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.788   0.719   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.788   2.259   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.122   3.029   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.454   3.029   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.121   2.259   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.121   0.719   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.454  -0.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.454  -1.591   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.121  -2.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.787  -1.591   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.787  -0.051   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.547  -2.361   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.547  -3.901   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.121  -3.901   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.787  -4.671   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.788  -0.821   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.788   3.799   0.000  0.00  0.00           H+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21   30                                             
CONECT   16   15   17   18   31                                             
CONECT   17   16    1                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0034436
HETATM    1  C1  UNL     1       6.501  -1.710   0.638  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.367  -0.451   0.248  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.575   0.411   0.004  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.053   0.134   0.034  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.935  -0.813   0.381  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.834   0.195   0.671  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.428   1.431   0.927  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.588   2.486   1.218  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.219   2.346   1.258  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.687   1.086   0.993  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.477  -0.004   0.697  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.890  -1.234   0.442  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.425  -1.230  -0.117  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.318  -0.644  -1.485  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.350   0.304  -1.759  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.613   0.103  -1.222  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.780   0.293  -1.948  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.995   0.058  -1.298  1.00  0.00           C  
HETATM   19  O3  UNL     1      -6.179   0.229  -1.961  1.00  0.00           O  
HETATM   20  C17 UNL     1      -6.157   0.645  -3.312  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.021  -0.348   0.019  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.251  -0.565   0.612  1.00  0.00           O  
HETATM   23  C19 UNL     1      -6.312  -0.983   1.963  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.862  -0.535   0.735  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.650  -0.307   0.108  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.355  -0.475   0.791  1.00  0.00           C  
HETATM   27  C23 UNL     1      -0.769   0.871   1.021  1.00  0.00           C  
HETATM   28  O5  UNL     1      -1.483   1.879   1.249  1.00  0.00           O  
HETATM   29  O6  UNL     1       4.814   1.296   0.821  1.00  0.00           O  
HETATM   30  H1  UNL     1       7.537  -2.071   0.768  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.658  -2.355   0.815  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.722   0.596  -1.071  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.366   1.380   0.537  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.479  -0.039   0.415  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.893   0.458  -1.027  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.089  -1.313   1.384  1.00  0.00           H  
HETATM   37  H8  UNL     1       3.641  -1.501  -0.406  1.00  0.00           H  
HETATM   38  H9  UNL     1       3.055   3.463   1.420  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.551   3.163   1.484  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.751  -2.296  -0.120  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.657  -0.135  -1.660  1.00  0.00           H  
HETATM   42  H13 UNL     1      -0.395  -1.464  -2.228  1.00  0.00           H  
HETATM   43  H14 UNL     1      -3.733   0.610  -2.967  1.00  0.00           H  
HETATM   44  H15 UNL     1      -5.555   1.582  -3.376  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.640  -0.101  -3.962  1.00  0.00           H  
HETATM   46  H17 UNL     1      -7.164   0.857  -3.715  1.00  0.00           H  
HETATM   47  H18 UNL     1      -5.659  -0.369   2.627  1.00  0.00           H  
HETATM   48  H19 UNL     1      -5.931  -2.034   2.083  1.00  0.00           H  
HETATM   49  H20 UNL     1      -7.358  -1.001   2.325  1.00  0.00           H  
HETATM   50  H21 UNL     1      -3.855  -0.847   1.750  1.00  0.00           H  
HETATM   51  H22 UNL     1      -1.454  -1.051   1.734  1.00  0.00           H  
CONECT    1    2    2   30   31
CONECT    2    3    4
CONECT    3   32   33   34
CONECT    4    5   29   35
CONECT    5    6   36   37
CONECT    6    7    7   11
CONECT    7    8   29
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   11   27
CONECT   11   12
CONECT   12   13
CONECT   13   14   26   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   17   17   25
CONECT   17   18   43
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   44   45   46
CONECT   21   22   24
CONECT   22   23
CONECT   23   47   48   49
CONECT   24   25   25   50
CONECT   25   26
CONECT   26   27   51
CONECT   27   28   28
END

HMDB0034436
     RDKit          3D
Rotenone
 51 55  0  0  0  0  0  0  0  0999 V2000
    6.5014   -1.7100    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.4512    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5754    0.4115    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.1345    0.0340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9354   -0.8128    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1946    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279    1.4307    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881    2.4857    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.3457    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    1.0856    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -0.0044    0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -1.2335    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.2301   -0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3185   -0.6440   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.3038   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    0.1029   -1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7804    0.2932   -1.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9947    0.0584   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788    0.2289   -1.9612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    0.6453   -3.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -0.3476    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -0.5653    0.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3115   -0.9828    1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622   -0.5350    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6502   -0.3073    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -0.4754    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7693    0.8712    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8785    1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    1.2962    0.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5374   -2.0708    0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -2.3554    0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.5964   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3661    1.3802    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -0.0386    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    0.4580   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.3131    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -1.5013   -0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549    3.4632    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    3.1629    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507   -2.2959   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -0.1353   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -1.4636   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329    0.6095   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550    1.5820   -3.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6397   -0.1007   -3.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1640    0.8573   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6594   -0.3687    2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9307   -2.0342    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3582   -1.0015    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8552   -0.8473    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -1.0505    1.7338 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  0
 27 28  2  0
  7 29  1  0
 29  4  1  0
 11  6  1  0
 26 13  1  0
 27 10  1  0
 25 16  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
 13 40  1  6
 14 41  1  0
 14 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 26 51  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-cis-Rotenone	ChEBI
(-)-Rotenone	ChEBI
5'beta-Rotenone	ChEBI
[2R-(2alpha,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	ChEBI
Barbasco	ChEBI
Canex	ChEBI
Dactinol	ChEBI
Derris	ChEBI
Noxfire	ChEBI
Paraderil	ChEBI
Tubatoxin	ChEBI
5'b-Rotenone	Generator
5'Β-rotenone	Generator
[2R-(2a,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	Generator
[2R-(2Α,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	Generator
1,2,12,12a-tetrahydro-8,9-Dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one, 9ci	HMDB
Derrin	HMDB
Derris, jmaf	HMDB
Dri-kil	HMDB
Nicouline	HMDB
Noxfish	HMDB
Tubotoxin	HMDB

Chemical Formula

C₂₃H₂₂O₆

Average Molecular Weight

394.4172

Monoisotopic Molecular Weight

394.141638436

IUPAC Name

(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one

Traditional Name

(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one

CAS Registry Number

83-79-4

SMILES

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

InChI Identifier

InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChI Key

JUVIOZPCNVVQFO-HBGVWJBISA-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
Chromane
1-benzopyran
Benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:28201 )
rotenones (CHEBI:28201 )
rotenones (C07593 )
Rotenoid flavonoids (C07593 )
Pesticides (C07593 )
Rotenoid flavonoids (LMPK12060007 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0002 mg/mL at 20 °C	Not Available
LogP	4.10	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	202.516	30932474
[M+H]+	Baker	199.634	30932474
[M-H]-	Not Available	202.516	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001451
[M+H]+	Not Available	196.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001451

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.3	ALOGPS
logP	3.32	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.71 m³·mol⁻¹	ChemAxon
Polarizability	42.07 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]+	194.197	31661259
DarkChem	[M-H]-	193.809	31661259
DeepCCS	[M-2H]-	226.679	30932474
DeepCCS	[M+Na]+	202.061	30932474
AllCCS	[M+H]+	196.8	32859911
AllCCS	[M+H-H2O]+	194.0	32859911
AllCCS	[M+NH4]+	199.3	32859911
AllCCS	[M+Na]+	200.1	32859911
AllCCS	[M-H]-	199.5	32859911
AllCCS	[M+Na-2H]-	199.4	32859911
AllCCS	[M+HCOO]-	199.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rotenone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	4737.8	Standard polar	33892256
Rotenone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	3252.3	Standard non polar	33892256
Rotenone	[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C	3284.8	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 - Rotenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zi3-2549000000-930d18ff5e2d26d23e39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-3901000000-c340e02baee25cf6196b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF	splash10-0002-0009000000-358453a180ad1eac44bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF	splash10-0002-0129000000-cc8a296246aa7e1b7fec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF	splash10-03dm-0795000000-228bd7c35bed240b45ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-01ow-0698000000-a9e4b41be932783b0afd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-01ow-0698000000-8f6994cc1cf72104baf0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-03dm-0696000000-cbec904cb2f70ad2fab0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-03dl-0693000000-fb2d60cf107761a6c44d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-03dl-0693000000-5718e6cf640e3d715757	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF	splash10-03dl-0693000000-0e5df9ae944ec77aec31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 20V, Negative-QTOF	splash10-03dl-4669000000-0fb03940864d95c2078a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 55V, Positive-QTOF	splash10-03dl-0693000000-33cf33e1c5d6e621df3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 45V, Positive-QTOF	splash10-03dl-0693000000-209ca7e024f911e3b7d9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 10V, Negative-QTOF	splash10-0006-1449000000-3bc2601b53c203b7fa83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF	splash10-01oy-0964000000-acfb0099b12ab168b4a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 40V, Positive-QTOF	splash10-0007-0910000000-7b2d8dce16788bdf7747	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 15V, Positive-QTOF	splash10-0002-0129000000-64fb6c845a91bd3fb4b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 10V, Positive-QTOF	splash10-0002-0009000000-9e8d4cec92e24203cdbd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF	splash10-03dm-0695000000-e9e1241f5910716f0c92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF	splash10-03dm-0695000000-4af2f040a67e164c6325	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 10V, Positive-QTOF	splash10-0002-0129000000-36a830cd40ad8fbcdeee	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF	splash10-004s-1359000000-7b6f697fe59d525d48f9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 40V, Positive-QTOF	splash10-05r0-4931000000-2d664b8d3fd4ebfd86ce	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 10V, Negative-QTOF	splash10-0006-0009000000-fbc08106b7ba4d66b944	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 20V, Negative-QTOF	splash10-0006-0019000000-ac9b3c7e9dbdabbc9404	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotenone 40V, Negative-QTOF	splash10-0pbj-0924000000-7060b1a64eec50bf9c96	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

DB11457

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Rotenone

METLIN ID

Not Available

PubChem Compound

6758

PDB ID

Not Available

ChEBI ID

28201

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1280741

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Khar A, Ali AM, Begum Z, Pardhasaradhi BV, Varalakshmi C: Induction of apoptosis in AK-5 cells by rotenone involves participation of caspases. Indian J Biochem Biophys. 1999 Apr;36(2):77-81. [PubMed:10549166 ]
Tapias V, Cannon JR, Greenamyre JT: Melatonin treatment potentiates neurodegeneration in a rat rotenone Parkinson's disease model. J Neurosci Res. 2010 Feb 1;88(2):420-7. doi: 10.1002/jnr.22201. [PubMed:19681169 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rotenone (HMDB0034436)

MOL for HMDB0034436 (Rotenone)

3D MOL for HMDB0034436 (Rotenone)

3D SDF for HMDB0034436 (Rotenone)

3D-SDF for HMDB0034436 (Rotenone)

PDB for HMDB0034436 (Rotenone)

3D PDB for HMDB0034436 (Rotenone)

SMILES for HMDB0034436 (Rotenone)

INCHI for HMDB0034436 (Rotenone)

Structure for HMDB0034436 (Rotenone)

3D Structure for HMDB0034436 (Rotenone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra