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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:21:20 UTC

Update Date

2021-09-26 23:06:10 UTC

HMDB ID

HMDB0253147

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hexanitrohexaazaisowurtzitane

Description

CL-20, also known as HNIW, belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms. CL-20 is possibly neutral. A polycyclic cage that is hexaazaisowurtzitane in which all six amino hydrogens are replaced by nitro groups. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexanitrohexaazaisowurtzitane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexanitrohexaazaisowurtzitane 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

  Mrv1572004191602522D          

 30 33  0  0  0  0            999 V2000
    3.3001    0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056    0.4758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056    1.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    0.4758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -0.2773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    2.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8994    0.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8994    1.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    0.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    1.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -1.1023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    3.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1018   -0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1018    2.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217   -0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0839    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217    2.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -1.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -1.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    3.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    3.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  3  1  0  0  0  0
 12  2  1  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  2  0  0  0  0
 23 15  2  0  0  0  0
 24 15  2  0  0  0  0
 25 16  2  0  0  0  0
 26 16  2  0  0  0  0
 27 17  2  0  0  0  0
 28 17  2  0  0  0  0
 29 18  2  0  0  0  0
 30 18  2  0  0  0  0
M  END

HMDB0253147
     RDKit          3D
Hexanitrohexaazaisowurtzitane
 36 39  0  0  0  0  0  0  0  0999 V2000
    2.2616   -2.3261    2.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -2.2882    1.1779 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7712   -3.4519    0.4742 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3279   -1.1034    0.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8222   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816    0.6998   -0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    1.1268    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    2.2926    0.8689 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3480    3.3452    0.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    2.2876    1.2153 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8816    0.1018    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128    0.1050    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266   -1.0788    0.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -2.2416    1.4567 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6617   -2.8831    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.7329    2.6037 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2752   -0.8342   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.6860   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    1.1373    0.7129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    2.3089    1.1951 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3977    2.7921    2.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    2.9715    0.4899 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1051    1.1951   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    2.1351   -2.2755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3868    1.9097   -3.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050    3.4754   -1.9011 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0934   -1.2988   -1.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762   -2.1880   -2.3036 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8585   -3.2160   -2.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950   -1.9093   -3.4584 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0269   -1.1859   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    1.0469   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212    0.0960    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    0.0808    2.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -1.2360   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    1.0028   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 11  4  1  0
 19 12  1  0
 27  5  1  0
 23  6  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  CHG  8   2   1   3  -1   8   1  10  -1  14   1  16  -1  20   1  22  -1
M  CHG  4  24   1  26  -1  28   1  30  -1
M  END

  Mrv1572004191602522D          

 30 33  0  0  0  0            999 V2000
    3.3001    0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056    0.4758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056    1.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    0.4758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -0.2773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    2.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8994    0.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8994    1.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    0.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    1.6693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -1.1023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618    3.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1018   -0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1018    2.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217   -0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0839    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217    2.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -1.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -1.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    3.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    3.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  3  1  0  0  0  0
 12  2  1  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  2  0  0  0  0
 23 15  2  0  0  0  0
 24 15  2  0  0  0  0
 25 16  2  0  0  0  0
 26 16  2  0  0  0  0
 27 17  2  0  0  0  0
 28 17  2  0  0  0  0
 29 18  2  0  0  0  0
 30 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253147

> <DATABASE_NAME>
hmdb

> <SMILES>
O=N(=O)N1C2C3N(C4C(N3N(=O)=O)N(C(C1N4N(=O)=O)N2N(=O)=O)N(=O)=O)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N12O12/c19-13(20)7-1-2-8(14(21)22)5(7)6-9(15(23)24)3(11(1)17(27)28)4(10(6)16(25)26)12(2)18(29)30/h1-6H

> <INCHI_KEY>
NDYLCHGXSQOGMS-UHFFFAOYSA-N

> <FORMULA>
C6H6N12O12

> <MOLECULAR_WEIGHT>
438.186

> <EXACT_MASS>
438.022813681

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.19762801614656

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0³,¹¹.0⁵,⁹]dodecane

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
-0.1831163799999988

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
294.35999999999996

> <JCHEM_REFRACTIVITY>
81.51539999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanitrohexaazaisowurtzitane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253147
     RDKit          3D
Hexanitrohexaazaisowurtzitane
 36 39  0  0  0  0  0  0  0  0999 V2000
    2.2616   -2.3261    2.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -2.2882    1.1779 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7712   -3.4519    0.4742 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3279   -1.1034    0.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8222   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816    0.6998   -0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    1.1268    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    2.2926    0.8689 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3480    3.3452    0.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    2.2876    1.2153 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8816    0.1018    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128    0.1050    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266   -1.0788    0.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -2.2416    1.4567 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6617   -2.8831    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.7329    2.6037 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2752   -0.8342   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.6860   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    1.1373    0.7129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    2.3089    1.1951 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3977    2.7921    2.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    2.9715    0.4899 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1051    1.1951   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    2.1351   -2.2755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3868    1.9097   -3.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050    3.4754   -1.9011 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0934   -1.2988   -1.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762   -2.1880   -2.3036 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8585   -3.2160   -2.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950   -1.9093   -3.4584 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0269   -1.1859   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    1.0469   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212    0.0960    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    0.0808    2.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -1.2360   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    1.0028   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 11  4  1  0
 19 12  1  0
 27  5  1  0
 23  6  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  CHG  8   2   1   3  -1   8   1  10  -1  14   1  16  -1  20   1  22  -1
M  CHG  4  24   1  26  -1  28   1  30  -1
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       6.160   0.841   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.744   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.524   0.841   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.524   2.744   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.291   1.792   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.393   1.792   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.664   0.888   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.664   2.697   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.020   0.888   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.020   2.697   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.342  -0.518   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       5.342   4.102   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       9.146   0.469   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       9.146   3.116   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       1.538   0.469   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       1.538   3.116   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       5.342  -2.058   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.342   5.642   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       9.523  -1.024   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.250   1.542   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.527   2.436   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.523   4.609   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.161  -1.024   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.434   1.542   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.157   2.436   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.161   4.609   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.008  -2.828   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.676  -2.828   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.008   6.412   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.676   6.412   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    8   12                                                  
CONECT    3    4    9   11                                                  
CONECT    4    3   10   12                                                  
CONECT    5    6    7    8                                                  
CONECT    6    5    9   10                                                  
CONECT    7    1    5   13                                                  
CONECT    8    2    5   14                                                  
CONECT    9    3    6   15                                                  
CONECT   10    4    6   16                                                  
CONECT   11    1    3   17                                                  
CONECT   12    2    4   18                                                  
CONECT   13    7   19   20                                                  
CONECT   14    8   21   22                                                  
CONECT   15    9   23   24                                                  
CONECT   16   10   25   26                                                  
CONECT   17   11   27   28                                                  
CONECT   18   12   29   30                                                  
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   18                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0253147
HETATM    1  O1  UNL     1       2.262  -2.326   2.345  1.00  0.00           O  
HETATM    2  N1  UNL     1       1.798  -2.288   1.178  1.00  0.00           N1+
HETATM    3  O2  UNL     1       1.771  -3.452   0.474  1.00  0.00           O1-
HETATM    4  N2  UNL     1       1.328  -1.103   0.621  1.00  0.00           N  
HETATM    5  C1  UNL     1       1.184  -0.822  -0.792  1.00  0.00           C  
HETATM    6  C2  UNL     1       1.182   0.700  -0.886  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.402   1.127   0.477  1.00  0.00           N  
HETATM    8  N4  UNL     1       1.996   2.293   0.869  1.00  0.00           N1+
HETATM    9  O3  UNL     1       1.348   3.345   0.911  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.317   2.288   1.215  1.00  0.00           O1-
HETATM   11  C3  UNL     1       0.882   0.102   1.327  1.00  0.00           C  
HETATM   12  C4  UNL     1      -0.613   0.105   1.464  1.00  0.00           C  
HETATM   13  N5  UNL     1      -1.227  -1.079   0.840  1.00  0.00           N  
HETATM   14  N6  UNL     1      -1.691  -2.242   1.457  1.00  0.00           N1+
HETATM   15  O5  UNL     1      -2.662  -2.883   1.013  1.00  0.00           O  
HETATM   16  O6  UNL     1      -1.080  -2.733   2.604  1.00  0.00           O1-
HETATM   17  C5  UNL     1      -1.275  -0.834  -0.590  1.00  0.00           C  
HETATM   18  C6  UNL     1      -1.289   0.686  -0.661  1.00  0.00           C  
HETATM   19  N7  UNL     1      -1.274   1.137   0.713  1.00  0.00           N  
HETATM   20  N8  UNL     1      -1.786   2.309   1.195  1.00  0.00           N1+
HETATM   21  O7  UNL     1      -1.398   2.792   2.264  1.00  0.00           O  
HETATM   22  O8  UNL     1      -2.751   2.971   0.490  1.00  0.00           O1-
HETATM   23  N9  UNL     1      -0.105   1.195  -1.297  1.00  0.00           N  
HETATM   24  N10 UNL     1      -0.208   2.135  -2.276  1.00  0.00           N1+
HETATM   25  O9  UNL     1      -0.387   1.910  -3.490  1.00  0.00           O  
HETATM   26  O10 UNL     1      -0.105   3.475  -1.901  1.00  0.00           O1-
HETATM   27  N11 UNL     1      -0.093  -1.299  -1.249  1.00  0.00           N  
HETATM   28  N12 UNL     1      -0.176  -2.188  -2.304  1.00  0.00           N1+
HETATM   29  O11 UNL     1      -0.858  -3.216  -2.173  1.00  0.00           O  
HETATM   30  O12 UNL     1       0.495  -1.909  -3.458  1.00  0.00           O1-
HETATM   31  H1  UNL     1       2.027  -1.186  -1.388  1.00  0.00           H  
HETATM   32  H2  UNL     1       1.933   1.047  -1.590  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.321   0.096   2.345  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.925   0.081   2.532  1.00  0.00           H  
HETATM   35  H5  UNL     1      -2.175  -1.236  -1.061  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.168   1.003  -1.218  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5   11
CONECT    5    6   27   31
CONECT    6    7   23   32
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   11   12   33
CONECT   12   13   19   34
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   17   18   27   35
CONECT   18   19   23   36
CONECT   19   20
CONECT   20   21   21   22
CONECT   23   24
CONECT   24   25   25   26
CONECT   27   28
CONECT   28   29   29   30
END

HMDB0253147
     RDKit          3D
Hexanitrohexaazaisowurtzitane
 36 39  0  0  0  0  0  0  0  0999 V2000
    2.2616   -2.3261    2.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -2.2882    1.1779 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7712   -3.4519    0.4742 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3279   -1.1034    0.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8222   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1816    0.6998   -0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    1.1268    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    2.2926    0.8689 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3480    3.3452    0.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    2.2876    1.2153 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8816    0.1018    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128    0.1050    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266   -1.0788    0.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -2.2416    1.4567 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6617   -2.8831    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.7329    2.6037 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2752   -0.8342   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.6860   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    1.1373    0.7129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    2.3089    1.1951 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3977    2.7921    2.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    2.9715    0.4899 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1051    1.1951   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    2.1351   -2.2755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3868    1.9097   -3.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050    3.4754   -1.9011 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0934   -1.2988   -1.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762   -2.1880   -2.3036 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8585   -3.2160   -2.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950   -1.9093   -3.4584 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0269   -1.1859   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    1.0469   -1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212    0.0960    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    0.0808    2.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -1.2360   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    1.0028   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 11  4  1  0
 19 12  1  0
 27  5  1  0
 23  6  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  CHG  8   2   1   3  -1   8   1  10  -1  14   1  16  -1  20   1  22  -1
M  CHG  4  24   1  26  -1  28   1  30  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hexanitrohexaazaisowurtzitane	ChEBI
HNIW	ChEBI
Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo(4,5-b)pyrazine	ChEBI
Hexanitrohexaazaisowurzitane	MeSH

Chemical Formula

C₆H₆N₁₂O₁₂

Average Molecular Weight

438.186

Monoisotopic Molecular Weight

438.022813681

IUPAC Name

2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0³,¹¹.0⁵,⁹]dodecane

Traditional Name

hexanitrohexaazaisowurtzitane

CAS Registry Number

Not Available

SMILES

O=N(=O)N1C2C3N(C4C(N3N(=O)=O)N(C(C1N4N(=O)=O)N2N(=O)=O)N(=O)=O)N(=O)=O

InChI Identifier

InChI=1S/C6H6N12O12/c19-13(20)7-1-2-8(14(21)22)5(7)6-9(15(23)24)3(11(1)17(27)28)4(10(6)16(25)26)12(2)18(29)30/h1-6H

InChI Key

NDYLCHGXSQOGMS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Piperazines

Alternative Parents

Substituents

Piperazine
Imidazolidine
Organic nitro compound
Azacycle
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

N-nitro compound (CHEBI:77327 )
polycyclic cage (CHEBI:77327 )

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	2.69	ALOGPS
logP	-0.18	ChemAxon
logS	-4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	294.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.52 m³·mol⁻¹	ChemAxon
Polarizability	29.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	178.329	30932474
DeepCCS	[M-H]-	175.934	30932474
DeepCCS	[M-2H]-	208.875	30932474
DeepCCS	[M+Na]+	185.237	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	177.9	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	167.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexanitrohexaazaisowurtzitane	O=N(=O)N1C2C3N(C4C(N3N(=O)=O)N(C(C1N4N(=O)=O)N2N(=O)=O)N(=O)=O)N(=O)=O	5950.2	Standard polar	33892256
Hexanitrohexaazaisowurtzitane	O=N(=O)N1C2C3N(C4C(N3N(=O)=O)N(C(C1N4N(=O)=O)N2N(=O)=O)N(=O)=O)N(=O)=O	3447.3	Standard non polar	33892256
Hexanitrohexaazaisowurtzitane	O=N(=O)N1C2C3N(C4C(N3N(=O)=O)N(C(C1N4N(=O)=O)N2N(=O)=O)N(=O)=O)N(=O)=O	3396.4	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 - Hexanitrohexaazaisowurtzitane GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0000900000-bf2923b4ecfb6acb903d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanitrohexaazaisowurtzitane 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 - Hexanitrohexaazaisowurtzitane 10V, Positive-QTOF	splash10-000i-0000900000-951b8de347ff6326cea6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanitrohexaazaisowurtzitane 20V, Positive-QTOF	splash10-0f80-0001900000-7fe2397e8156bae39aaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanitrohexaazaisowurtzitane 40V, Positive-QTOF	splash10-0zgr-0008900000-aa62d734a74d511b731e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanitrohexaazaisowurtzitane 10V, Negative-QTOF	splash10-000i-1000900000-fa0d681a28358e18df3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanitrohexaazaisowurtzitane 20V, Negative-QTOF	splash10-000i-1000900000-eb3a74f525e1520c03d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanitrohexaazaisowurtzitane 40V, Negative-QTOF	splash10-0udi-0007900000-b7dc43d9b9073a487a33	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexanitrohexaazaisowurtzitane

METLIN ID

Not Available

PubChem Compound

9889323

PDB ID

Not Available

ChEBI ID

77327

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 Hexanitrohexaazaisowurtzitane (HMDB0253147)

MOL for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

3D MOL for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

3D SDF for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

3D-SDF for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

PDB for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

3D PDB for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

SMILES for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

INCHI for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

Structure for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

3D Structure for HMDB0253147 (Hexanitrohexaazaisowurtzitane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra