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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:45:24 UTC

Update Date

2021-09-26 23:16:41 UTC

HMDB ID

HMDB0259253

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trioctylphosphine oxide

Description

1-(dioctylphosphoryl)octane belongs to the class of organic compounds known as organophosphine oxides. These are organic compounds containing the phosphine oxide group, with the general formula R3P=O or R3P+O-. Based on a literature review very few articles have been published on 1-(dioctylphosphoryl)octane. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trioctylphosphine oxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trioctylphosphine oxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1572004191604192D          

 26 25  0  0  0  0            999 V2000
    3.9039    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2993    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0618    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -0.6039    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  2  0  0  0  0
M  END

HMDB0259253
     RDKit          3D
Trioctylphosphine oxide
 77 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    6.2966    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7456    4.7640    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116    4.3797   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1034    2.9093   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988    2.2908   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    2.8544   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.2853    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.8148    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.0541    1.4166 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.5804    0.7421    2.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.0162    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4592    1.2419   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    1.2297   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    1.1382    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2779    1.1630   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767    0.0047   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8895    0.0246   -1.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8391   -0.0718   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.6930    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.2599    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -3.7134    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851   -3.8698    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -5.3063    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851   -5.4121    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595   -4.5831    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814   -5.0232   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8085    6.5897   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    6.7398   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899    6.5618    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7744    4.3918    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055    4.3960    0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    4.7862   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430    4.8598   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0857    2.3847   -1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6654    2.6689   -2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890    2.4678    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1938    1.1745   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    3.9698   -0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3814    2.6995   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    2.5842    1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    2.7724    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    0.3309    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.5883   -0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -0.0654    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -0.8696    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147    1.3379   -0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210    2.1026    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230    2.1827   -1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897    0.4199   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    2.0632    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534    0.2633    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9948    1.1507    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853    2.1148   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    0.1238   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2383   -0.9507   -0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0112    0.9375   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9888   -0.9142   -2.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6841   -0.7071   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3553   -0.5718    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1462    0.9398   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8759   -2.1980    2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.7765    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9207   -1.6380   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731   -2.1804   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2380   -4.3296    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -4.0486   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -3.2208    0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.5831    1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -5.9068    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -5.7220   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -5.0882    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -6.4889    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -3.5238    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7390   -4.7189    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466   -5.1552   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -5.9715   -0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870   -4.2499   -1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  0
 25 74  1  0
 26 75  1  0
 26 76  1  0
 26 77  1  0
M  END


  Mrv1572004191604192D          

 26 25  0  0  0  0            999 V2000
    3.9039    4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2993    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0618    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -0.6039    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259253

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3

> <INCHI_KEY>
ZMBHCYHQLYEYDV-UHFFFAOYSA-N

> <FORMULA>
C24H51OP

> <MOLECULAR_WEIGHT>
386.645

> <EXACT_MASS>
386.36775326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.77370802626395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(dioctylphosphoryl)octane

> <ALOGPS_LOGP>
8.06

> <JCHEM_LOGP>
7.288686051666667

> <ALOGPS_LOGS>
-7.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.502608233648148

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
121.06319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trioctylphosphine oxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259253
     RDKit          3D
Trioctylphosphine oxide
 77 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    6.2966    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7456    4.7640    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116    4.3797   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1034    2.9093   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988    2.2908   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    2.8544   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.2853    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.8148    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.0541    1.4166 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.5804    0.7421    2.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.0162    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4592    1.2419   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    1.2297   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    1.1382    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2779    1.1630   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767    0.0047   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8895    0.0246   -1.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8391   -0.0718   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.6930    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.2599    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -3.7134    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851   -3.8698    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -5.3063    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851   -5.4121    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595   -4.5831    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814   -5.0232   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8085    6.5897   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    6.7398   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899    6.5618    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7744    4.3918    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055    4.3960    0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    4.7862   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430    4.8598   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0857    2.3847   -1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6654    2.6689   -2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890    2.4678    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1938    1.1745   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    3.9698   -0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3814    2.6995   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    2.5842    1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    2.7724    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    0.3309    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.5883   -0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -0.0654    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -0.8696    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147    1.3379   -0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210    2.1026    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230    2.1827   -1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897    0.4199   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    2.0632    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534    0.2633    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9948    1.1507    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853    2.1148   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    0.1238   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2383   -0.9507   -0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0112    0.9375   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9888   -0.9142   -2.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6841   -0.7071   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3553   -0.5718    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1462    0.9398   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8759   -2.1980    2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.7765    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9207   -1.6380   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731   -2.1804   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2380   -4.3296    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -4.0486   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -3.2208    0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.5831    1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -5.9068    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -5.7220   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -5.0882    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -6.4889    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -3.5238    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7390   -4.7189    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466   -5.1552   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -5.9715   -0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870   -4.2499   -1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
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 14 51  1  0
 15 52  1  0
 15 53  1  0
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 26 75  1  0
 26 76  1  0
 26 77  1  0
M  END

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       7.287   8.113   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.862   4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.621   7.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.092   2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621   5.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.552   2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.955   5.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.782   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.955   3.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.242   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.288   2.723   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.472   0.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.288   1.183   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.932   0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.288  -3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.622   0.413   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.162  -1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.622  -2.667   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.082  -1.127   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0      12.622  -1.127   0.000  0.00  0.00           P+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23                                                       
CONECT   21   18   24                                                       
CONECT   22   19   26                                                       
CONECT   23   20   26                                                       
CONECT   24   21   26                                                       
CONECT   25   26                                                            
CONECT   26   22   23   24   25                                             
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0259253
HETATM    1  C1  UNL     1      -4.838   6.297   0.166  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.746   4.764   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.212   4.380  -1.265  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.103   2.909  -1.401  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.199   2.291  -0.372  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.828   2.854  -0.506  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.821   2.285   0.484  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.702   0.815   0.287  1.00  0.00           C  
HETATM    9  P1  UNL     1       0.493   0.054   1.417  1.00  0.00           P  
HETATM   10  O1  UNL     1       0.580   0.742   2.743  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.170   0.016   0.696  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.459   1.242  -0.088  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.806   1.230  -0.709  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.902   1.138   0.309  1.00  0.00           C  
HETATM   15  C13 UNL     1       6.278   1.163  -0.269  1.00  0.00           C  
HETATM   16  C14 UNL     1       6.477   0.005  -1.199  1.00  0.00           C  
HETATM   17  C15 UNL     1       7.890   0.025  -1.768  1.00  0.00           C  
HETATM   18  C16 UNL     1       8.839  -0.072  -0.607  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.006  -1.693   1.637  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.158  -2.260   0.246  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.567  -3.713   0.231  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.885  -3.870   0.921  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.362  -5.306   0.938  1.00  0.00           C  
HETATM   24  C22 UNL     1      -3.685  -5.412   1.643  1.00  0.00           C  
HETATM   25  C23 UNL     1      -4.759  -4.583   0.969  1.00  0.00           C  
HETATM   26  C24 UNL     1      -4.981  -5.023  -0.468  1.00  0.00           C  
HETATM   27  H1  UNL     1      -5.808   6.590  -0.247  1.00  0.00           H  
HETATM   28  H2  UNL     1      -4.006   6.740  -0.424  1.00  0.00           H  
HETATM   29  H3  UNL     1      -4.690   6.562   1.228  1.00  0.00           H  
HETATM   30  H4  UNL     1      -5.774   4.392   0.253  1.00  0.00           H  
HETATM   31  H5  UNL     1      -4.105   4.396   0.906  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.897   4.786  -2.059  1.00  0.00           H  
HETATM   33  H7  UNL     1      -3.243   4.860  -1.446  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.086   2.385  -1.403  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.665   2.669  -2.417  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.589   2.468   0.665  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.194   1.174  -0.457  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.892   3.970  -0.353  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.381   2.700  -1.508  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.060   2.584   1.521  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.154   2.772   0.218  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.691   0.331   0.538  1.00  0.00           H  
HETATM   43  H17 UNL     1      -0.400   0.588  -0.735  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.921  -0.065   1.528  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.305  -0.870   0.047  1.00  0.00           H  
HETATM   46  H20 UNL     1       1.715   1.338  -0.906  1.00  0.00           H  
HETATM   47  H21 UNL     1       2.421   2.103   0.614  1.00  0.00           H  
HETATM   48  H22 UNL     1       3.923   2.183  -1.311  1.00  0.00           H  
HETATM   49  H23 UNL     1       3.890   0.420  -1.498  1.00  0.00           H  
HETATM   50  H24 UNL     1       4.809   2.063   0.953  1.00  0.00           H  
HETATM   51  H25 UNL     1       4.753   0.263   0.981  1.00  0.00           H  
HETATM   52  H26 UNL     1       6.995   1.151   0.584  1.00  0.00           H  
HETATM   53  H27 UNL     1       6.385   2.115  -0.835  1.00  0.00           H  
HETATM   54  H28 UNL     1       5.753   0.124  -2.050  1.00  0.00           H  
HETATM   55  H29 UNL     1       6.238  -0.951  -0.699  1.00  0.00           H  
HETATM   56  H30 UNL     1       8.011   0.937  -2.356  1.00  0.00           H  
HETATM   57  H31 UNL     1       7.989  -0.914  -2.380  1.00  0.00           H  
HETATM   58  H32 UNL     1       9.684  -0.707  -0.905  1.00  0.00           H  
HETATM   59  H33 UNL     1       8.355  -0.572   0.280  1.00  0.00           H  
HETATM   60  H34 UNL     1       9.146   0.940  -0.271  1.00  0.00           H  
HETATM   61  H35 UNL     1       0.876  -2.198   2.091  1.00  0.00           H  
HETATM   62  H36 UNL     1      -0.915  -1.776   2.235  1.00  0.00           H  
HETATM   63  H37 UNL     1      -0.921  -1.638  -0.289  1.00  0.00           H  
HETATM   64  H38 UNL     1       0.773  -2.180  -0.339  1.00  0.00           H  
HETATM   65  H39 UNL     1       0.238  -4.330   0.679  1.00  0.00           H  
HETATM   66  H40 UNL     1      -0.652  -4.049  -0.823  1.00  0.00           H  
HETATM   67  H41 UNL     1      -2.612  -3.221   0.393  1.00  0.00           H  
HETATM   68  H42 UNL     1      -1.788  -3.583   1.999  1.00  0.00           H  
HETATM   69  H43 UNL     1      -1.633  -5.907   1.517  1.00  0.00           H  
HETATM   70  H44 UNL     1      -2.456  -5.722  -0.088  1.00  0.00           H  
HETATM   71  H45 UNL     1      -3.619  -5.088   2.687  1.00  0.00           H  
HETATM   72  H46 UNL     1      -4.000  -6.489   1.586  1.00  0.00           H  
HETATM   73  H47 UNL     1      -4.508  -3.524   1.057  1.00  0.00           H  
HETATM   74  H48 UNL     1      -5.739  -4.719   1.477  1.00  0.00           H  
HETATM   75  H49 UNL     1      -6.047  -5.155  -0.714  1.00  0.00           H  
HETATM   76  H50 UNL     1      -4.416  -5.972  -0.604  1.00  0.00           H  
HETATM   77  H51 UNL     1      -4.587  -4.250  -1.165  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   10   11   19
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   58   59   60
CONECT   19   20   61   62
CONECT   20   21   63   64
CONECT   21   22   65   66
CONECT   22   23   67   68
CONECT   23   24   69   70
CONECT   24   25   71   72
CONECT   25   26   73   74
CONECT   26   75   76   77
END

HMDB0259253
     RDKit          3D
Trioctylphosphine oxide
 77 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    6.2966    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7456    4.7640    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116    4.3797   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1034    2.9093   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988    2.2908   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    2.8544   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.2853    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    0.8148    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    0.0541    1.4166 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.5804    0.7421    2.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.0162    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4592    1.2419   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062    1.2297   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    1.1382    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2779    1.1630   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767    0.0047   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8895    0.0246   -1.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8391   -0.0718   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.6930    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.2599    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -3.7134    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851   -3.8698    0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -5.3063    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851   -5.4121    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595   -4.5831    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9814   -5.0232   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8085    6.5897   -0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    6.7398   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899    6.5618    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7744    4.3918    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055    4.3960    0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    4.7862   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430    4.8598   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0857    2.3847   -1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6654    2.6689   -2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890    2.4678    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1938    1.1745   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    3.9698   -0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3814    2.6995   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    2.5842    1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    2.7724    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    0.3309    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.5883   -0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -0.0654    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -0.8696    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147    1.3379   -0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210    2.1026    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230    2.1827   -1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897    0.4199   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    2.0632    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534    0.2633    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9948    1.1507    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853    2.1148   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    0.1238   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2383   -0.9507   -0.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0112    0.9375   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9888   -0.9142   -2.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6841   -0.7071   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3553   -0.5718    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1462    0.9398   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8759   -2.1980    2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.7765    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9207   -1.6380   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731   -2.1804   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2380   -4.3296    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -4.0486   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -3.2208    0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.5831    1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -5.9068    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562   -5.7220   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -5.0882    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -6.4889    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -3.5238    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7390   -4.7189    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0466   -5.1552   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -5.9715   -0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870   -4.2499   -1.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  0
 25 74  1  0
 26 75  1  0
 26 76  1  0
 26 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
TOPO	MeSH
Tri-N-octylphosphine oxide	MeSH
Trioctyl phosphine oxide	MeSH
Trioctylphosphine oxide	MeSH
Cyanex 921	MeSH

Chemical Formula

C₂₄H₅₁OP

Average Molecular Weight

386.645

Monoisotopic Molecular Weight

386.36775326

IUPAC Name

1-(dioctylphosphoryl)octane

Traditional Name

trioctylphosphine oxide

CAS Registry Number

Not Available

SMILES

CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC

InChI Identifier

InChI=1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3

InChI Key

ZMBHCYHQLYEYDV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organophosphine oxides. These are organic compounds containing the phosphine oxide group, with the general formula R3P=O or R3P+O-.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organic phosphines and derivatives

Sub Class

Organophosphine oxides

Direct Parent

Organophosphine oxides

Alternative Parents

Substituents

Organophosphine oxide
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	8.06	ALOGPS
logP	7.29	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	121.06 m³·mol⁻¹	ChemAxon
Polarizability	52.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	202.899	30932474
DeepCCS	[M-H]-	200.541	30932474
DeepCCS	[M-2H]-	233.427	30932474
DeepCCS	[M+Na]+	209.114	30932474
AllCCS	[M+H]+	216.0	32859911
AllCCS	[M+H-H2O]+	214.3	32859911
AllCCS	[M+NH4]+	217.5	32859911
AllCCS	[M+Na]+	218.0	32859911
AllCCS	[M-H]-	201.8	32859911
AllCCS	[M+Na-2H]-	203.1	32859911
AllCCS	[M+HCOO]-	204.8	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.	10.65 minutes	32390414
Predicted by Siyang on May 30, 2022	34.553 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3800.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	858.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	346.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	409.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	689.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1432.8 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	905.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2811.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	792.8 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	2657.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	982.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	591.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	600.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	770.8 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trioctylphosphine oxide	CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC	3006.0	Standard polar	33892256
Trioctylphosphine oxide	CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC	2637.9	Standard non polar	33892256
Trioctylphosphine oxide	CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC	2763.7	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 - Trioctylphosphine oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9113000000-fee66d333fc80b760beb	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trioctylphosphine oxide 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 - Trioctylphosphine oxide 10V, Positive-QTOF	splash10-000i-1209000000-3b1efcd44ca77f1645b6	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioctylphosphine oxide 20V, Positive-QTOF	splash10-03y0-4679000000-6b9dea0ace144f2fb87f	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioctylphosphine oxide 40V, Positive-QTOF	splash10-06r6-9430000000-1a9361f3a6e61151af60	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioctylphosphine oxide 10V, Negative-QTOF	splash10-000i-0019000000-59070933ca15fcedcf2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioctylphosphine oxide 20V, Negative-QTOF	splash10-01p9-0839000000-64b2dd8c94c241d4fd11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioctylphosphine oxide 40V, Negative-QTOF	splash10-08fr-1920000000-854147c047a9d6b67499	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Trioctylphosphine oxide (HMDB0259253)

MOL for HMDB0259253 (Trioctylphosphine oxide)

3D MOL for HMDB0259253 (Trioctylphosphine oxide)

3D SDF for HMDB0259253 (Trioctylphosphine oxide)

3D-SDF for HMDB0259253 (Trioctylphosphine oxide)

PDB for HMDB0259253 (Trioctylphosphine oxide)

3D PDB for HMDB0259253 (Trioctylphosphine oxide)

SMILES for HMDB0259253 (Trioctylphosphine oxide)

INCHI for HMDB0259253 (Trioctylphosphine oxide)

Structure for HMDB0259253 (Trioctylphosphine oxide)

3D Structure for HMDB0259253 (Trioctylphosphine oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra