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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:58:02 UTC

Update Date

2021-09-26 23:06:45 UTC

HMDB ID

HMDB0253485

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ingenol mebutate

Description

5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. 5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Ingenol mebutate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ingenol mebutate 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


  Mrv1533004241509282D          

 31 34  0  0  0  0            999 V2000
   -3.8291    1.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322    0.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970   -0.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692   -0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -1.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7384    0.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -1.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929   -1.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261   -0.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -1.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -2.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097   -1.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    0.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2746    1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879    2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702    2.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167    0.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315    1.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    0.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424   -0.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716   -0.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636   -1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -1.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  9 31  1  0  0  0  0
M  END

HMDB0253485
     RDKit          3D
Ingenol mebutate
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.6990   -0.9695   -1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.4748   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -0.1529    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1048   -0.2867    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557    0.3283    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743    0.6369    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    0.4603   -0.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738    0.9359    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    2.1589   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877    3.1550   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    2.1582   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.9225   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.3272   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.9202   -2.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6216   -0.8524   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -2.0309   -1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.2097   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921   -3.6372   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -3.6217   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -1.2668    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668   -1.2436    1.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685    0.0208   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -0.2548   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8889    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984    0.3161    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    1.5538    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    1.3275    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734    2.6750    1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985   -0.1995    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9828   -0.8735    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971    0.4369   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8153   -1.0000   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797   -0.2578   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9022   -1.9441   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.3764   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -0.3352    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6860   -1.2216    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.5416    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1399    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.5993   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.7800   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.8402   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    2.9294   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.9495   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.8405   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712   -4.2679   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -4.0545    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911   -3.9521   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -1.7237    0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796   -1.9332    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -0.3878   -1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -1.8797    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.1920    2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.9048   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    2.3751    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.6385    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727    3.3279    0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200    3.2260    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080    2.5524    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2844   -1.7872    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6907   -1.1782    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7643   -0.1147    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2159    0.8621   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -0.3203   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5587    1.2444   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 29 31  1  0
 22  8  1  0
 29 24  1  0
 22 12  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
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 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
M  END


  Mrv1533004241509282D          

 31 34  0  0  0  0            999 V2000
   -3.8291    1.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322    0.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970   -0.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692   -0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -1.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7384    0.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -1.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929   -1.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261   -0.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -1.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -2.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097   -1.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    0.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2746    1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879    2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702    2.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167    0.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315    1.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    0.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424   -0.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716   -0.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636   -1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -1.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  9 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253485

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C(C)C(=O)OC1C(C)=CC23C(C)CC4C(C(C=C(CO)C(O)C12O)C3=O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3

> <INCHI_KEY>
VDJHFHXMUKFKET-UHFFFAOYSA-N

> <FORMULA>
C25H34O6

> <MOLECULAR_WEIGHT>
430.541

> <EXACT_MASS>
430.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.3796375337762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.505605261

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.444218810904726

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.091182222993204

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637287828251944

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
117.85669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253485
     RDKit          3D
Ingenol mebutate
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.6990   -0.9695   -1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.4748   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -0.1529    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1048   -0.2867    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557    0.3283    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743    0.6369    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    0.4603   -0.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738    0.9359    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    2.1589   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877    3.1550   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    2.1582   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.9225   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.3272   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.9202   -2.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6216   -0.8524   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -2.0309   -1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.2097   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921   -3.6372   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -3.6217   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -1.2668    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668   -1.2436    1.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685    0.0208   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -0.2548   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8889    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984    0.3161    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    1.5538    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    1.3275    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734    2.6750    1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985   -0.1995    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9828   -0.8735    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971    0.4369   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8153   -1.0000   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797   -0.2578   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9022   -1.9441   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.3764   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -0.3352    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6860   -1.2216    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.5416    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1399    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.5993   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.7800   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.8402   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    2.9294   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.9495   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.8405   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712   -4.2679   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -4.0545    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911   -3.9521   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -1.7237    0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796   -1.9332    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -0.3878   -1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -1.8797    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.1920    2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.9048   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    2.3751    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.6385    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727    3.3279    0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200    3.2260    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080    2.5524    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2844   -1.7872    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6907   -1.1782    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7643   -0.1147    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2159    0.8621   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -0.3203   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5587    1.2444   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 29 31  1  0
 22  8  1  0
 29 24  1  0
 22 12  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -7.148   2.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.847   1.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.910   0.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.274  -0.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.609  -0.505   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.673  -2.044   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.245   0.209   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.944  -0.615   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.868  -2.161   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.360  -2.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.609  -1.227   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.474  -2.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.544  -3.861   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.005  -3.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.241  -2.091   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.187  -0.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.956   0.469   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.379   1.937   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.906   2.474   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.724   4.003   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.691   4.611   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.404   1.604   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.739   2.373   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.503  -0.019   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.757   0.875   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.759  -0.401   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.661  -1.650   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.547  -1.274   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.777  -0.347   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.839  -2.113   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.049  -3.150   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24   26                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   11   25                                             
CONECT   25   24                                                            
CONECT   26   17   11   27                                                  
CONECT   27   26                                                            
CONECT   28   16   15   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    9                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0253485
HETATM    1  C1  UNL     1      -6.699  -0.969  -1.206  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.349  -0.475  -0.829  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.062  -0.153   0.412  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.105  -0.287   1.450  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.756   0.328   0.789  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.474   0.637   1.968  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.753   0.460  -0.192  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.474   0.936   0.201  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.149   2.159  -0.618  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.188   3.155  -0.980  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.155   2.158  -0.923  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.792   0.923  -0.321  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.795   0.327  -1.240  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.930   0.920  -2.286  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.622  -0.852  -1.050  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.716  -2.031  -1.041  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.585  -2.210  -0.375  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.092  -3.637  -0.429  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.173  -3.622  -1.027  1.00  0.00           O  
HETATM   20  C16 UNL     1      -0.268  -1.267   0.402  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.067  -1.244   1.744  1.00  0.00           O  
HETATM   22  C17 UNL     1      -0.369   0.021  -0.274  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.701  -0.255  -1.631  1.00  0.00           O  
HETATM   24  C18 UNL     1       3.446  -0.889   0.183  1.00  0.00           C  
HETATM   25  C19 UNL     1       3.698   0.316   0.927  1.00  0.00           C  
HETATM   26  C20 UNL     1       2.941   1.554   0.613  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.449   1.328   0.928  1.00  0.00           C  
HETATM   28  C22 UNL     1       0.973   2.675   1.468  1.00  0.00           C  
HETATM   29  C23 UNL     1       4.799  -0.199   0.085  1.00  0.00           C  
HETATM   30  C24 UNL     1       5.983  -0.873   0.794  1.00  0.00           C  
HETATM   31  C25 UNL     1       5.197   0.437  -1.212  1.00  0.00           C  
HETATM   32  H1  UNL     1      -6.815  -1.000  -2.305  1.00  0.00           H  
HETATM   33  H2  UNL     1      -7.480  -0.258  -0.838  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.902  -1.944  -0.714  1.00  0.00           H  
HETATM   35  H4  UNL     1      -4.589  -0.376  -1.582  1.00  0.00           H  
HETATM   36  H5  UNL     1      -5.659  -0.335   2.470  1.00  0.00           H  
HETATM   37  H6  UNL     1      -6.686  -1.222   1.321  1.00  0.00           H  
HETATM   38  H7  UNL     1      -6.831   0.542   1.460  1.00  0.00           H  
HETATM   39  H8  UNL     1      -1.457   1.140   1.267  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.110   2.599  -1.233  1.00  0.00           H  
HETATM   41  H10 UNL     1      -2.399   3.780  -0.066  1.00  0.00           H  
HETATM   42  H11 UNL     1      -1.853   3.840  -1.782  1.00  0.00           H  
HETATM   43  H12 UNL     1       0.642   2.929  -1.506  1.00  0.00           H  
HETATM   44  H13 UNL     1       3.335  -0.950  -1.916  1.00  0.00           H  
HETATM   45  H14 UNL     1       2.046  -2.841  -1.670  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.771  -4.268  -1.027  1.00  0.00           H  
HETATM   47  H16 UNL     1       0.024  -4.055   0.609  1.00  0.00           H  
HETATM   48  H17 UNL     1      -1.091  -3.952  -1.939  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.307  -1.724   0.378  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.780  -1.933   1.874  1.00  0.00           H  
HETATM   51  H20 UNL     1      -1.677  -0.388  -1.719  1.00  0.00           H  
HETATM   52  H21 UNL     1       3.498  -1.880   0.724  1.00  0.00           H  
HETATM   53  H22 UNL     1       3.863   0.192   2.040  1.00  0.00           H  
HETATM   54  H23 UNL     1       3.003   1.905  -0.425  1.00  0.00           H  
HETATM   55  H24 UNL     1       3.358   2.375   1.245  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.433   0.638   1.767  1.00  0.00           H  
HETATM   57  H26 UNL     1       0.573   3.328   0.703  1.00  0.00           H  
HETATM   58  H27 UNL     1       1.820   3.226   1.959  1.00  0.00           H  
HETATM   59  H28 UNL     1       0.208   2.552   2.262  1.00  0.00           H  
HETATM   60  H29 UNL     1       6.284  -1.787   0.263  1.00  0.00           H  
HETATM   61  H30 UNL     1       5.691  -1.178   1.824  1.00  0.00           H  
HETATM   62  H31 UNL     1       6.764  -0.115   0.870  1.00  0.00           H  
HETATM   63  H32 UNL     1       6.216   0.862  -1.076  1.00  0.00           H  
HETATM   64  H33 UNL     1       5.271  -0.320  -2.045  1.00  0.00           H  
HETATM   65  H34 UNL     1       4.559   1.244  -1.559  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   35
CONECT    3    4    5
CONECT    4   36   37   38
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   22   39
CONECT    9   10   11   11
CONECT   10   40   41   42
CONECT   11   12   43
CONECT   12   13   22   27
CONECT   13   14   14   15
CONECT   15   16   24   44
CONECT   16   17   17   45
CONECT   17   18   20
CONECT   18   19   46   47
CONECT   19   48
CONECT   20   21   22   49
CONECT   21   50
CONECT   22   23
CONECT   23   51
CONECT   24   25   29   52
CONECT   25   26   29   53
CONECT   26   27   54   55
CONECT   27   28   56
CONECT   28   57   58   59
CONECT   29   30   31
CONECT   30   60   61   62
CONECT   31   63   64   65
END

HMDB0253485
     RDKit          3D
Ingenol mebutate
 65 68  0  0  0  0  0  0  0  0999 V2000
   -6.6990   -0.9695   -1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.4748   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -0.1529    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1048   -0.2867    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557    0.3283    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743    0.6369    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    0.4603   -0.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738    0.9359    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    2.1589   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877    3.1550   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    2.1582   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.9225   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.3272   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.9202   -2.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6216   -0.8524   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -2.0309   -1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.2097   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921   -3.6372   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -3.6217   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -1.2668    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668   -1.2436    1.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685    0.0208   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010   -0.2548   -1.6307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8889    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984    0.3161    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    1.5538    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    1.3275    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734    2.6750    1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985   -0.1995    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9828   -0.8735    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971    0.4369   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8153   -1.0000   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4797   -0.2578   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9022   -1.9441   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -0.3764   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -0.3352    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6860   -1.2216    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.5416    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1399    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105    2.5993   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.7800   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.8402   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    2.9294   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.9495   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.8405   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712   -4.2679   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -4.0545    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911   -3.9521   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -1.7237    0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796   -1.9332    1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -0.3878   -1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -1.8797    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.1920    2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    1.9048   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    2.3751    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.6385    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727    3.3279    0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200    3.2260    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080    2.5524    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2844   -1.7872    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6907   -1.1782    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7643   -0.1147    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2159    0.8621   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -0.3203   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5587    1.2444   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 29 31  1  0
 22  8  1  0
 29 24  1  0
 22 12  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₄O₆

Average Molecular Weight

430.541

Monoisotopic Molecular Weight

430.235538815

IUPAC Name

5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate

Traditional Name

5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C(C)=CC23C(C)CC4C(C(C=C(CO)C(O)C12O)C3=O)C4(C)C

InChI Identifier

InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3

InChI Key

VDJHFHXMUKFKET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	2.49	ALOGPS
logP	2.51	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.86 m³·mol⁻¹	ChemAxon
Polarizability	46.38 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	242.443	30932474
DeepCCS	[M+Na]+	217.886	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ingenol mebutate	CC=C(C)C(=O)OC1C(C)=CC23C(C)CC4C(C(C=C(CO)C(O)C12O)C3=O)C4(C)C	3925.8	Standard polar	33892256
Ingenol mebutate	CC=C(C)C(=O)OC1C(C)=CC23C(C)CC4C(C(C=C(CO)C(O)C12O)C3=O)C4(C)C	3086.5	Standard non polar	33892256
Ingenol mebutate	CC=C(C)C(=O)OC1C(C)=CC23C(C)CC4C(C(C=C(CO)C(O)C12O)C3=O)C4(C)C	3086.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ingenol mebutate,4TMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C)=C(C=C(CO[Si](C)(C)C)C(O[Si](C)(C)C)C12O[Si](C)(C)C)C1C(CC3C)C1(C)C	2918.4	Semi standard non polar	33892256
Ingenol mebutate,4TMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C)=C(C=C(CO[Si](C)(C)C)C(O[Si](C)(C)C)C12O[Si](C)(C)C)C1C(CC3C)C1(C)C	3155.3	Standard non polar	33892256
Ingenol mebutate,4TMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C)=C(C=C(CO[Si](C)(C)C)C(O[Si](C)(C)C)C12O[Si](C)(C)C)C1C(CC3C)C1(C)C	3404.9	Standard polar	33892256
Ingenol mebutate,4TBDMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C(C)(C)C)=C(C=C(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C)C1C(CC3C)C1(C)C	3736.8	Semi standard non polar	33892256
Ingenol mebutate,4TBDMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C(C)(C)C)=C(C=C(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C)C1C(CC3C)C1(C)C	3829.8	Standard non polar	33892256
Ingenol mebutate,4TBDMS,isomer #1	CC=C(C)C(=O)OC1C(C)=CC23C(O[Si](C)(C)C(C)(C)C)=C(C=C(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C)C1C(CC3C)C1(C)C	3686.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ce9-9112200000-29e83191c7b698a0e9bf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ingenol mebutate GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-04	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 - Ingenol mebutate 10V, Positive-QTOF	splash10-001i-0001900000-aa5896388854d5fa8300	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ingenol mebutate 20V, Positive-QTOF	splash10-001i-1009400000-88e0e34033bd1ae2bebb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ingenol mebutate 40V, Positive-QTOF	splash10-0a4i-9106100000-f41daba4986ea9b30d1d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ingenol mebutate 10V, Negative-QTOF	splash10-004i-0000900000-d272a08ad49f2974aa83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ingenol mebutate 20V, Negative-QTOF	splash10-004i-0002900000-0fe2e8c4249d9ab4d072	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ingenol mebutate 40V, Negative-QTOF	splash10-0pvi-9112000000-8ea5fe30ee6c7d79eb15	2021-10-12	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

Not Available

METLIN ID

Not Available

PubChem Compound

73234850

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 Ingenol mebutate (HMDB0253485)

MOL for HMDB0253485 (Ingenol mebutate)

3D MOL for HMDB0253485 (Ingenol mebutate)

3D SDF for HMDB0253485 (Ingenol mebutate)

3D-SDF for HMDB0253485 (Ingenol mebutate)

PDB for HMDB0253485 (Ingenol mebutate)

3D PDB for HMDB0253485 (Ingenol mebutate)

SMILES for HMDB0253485 (Ingenol mebutate)

INCHI for HMDB0253485 (Ingenol mebutate)

Structure for HMDB0253485 (Ingenol mebutate)

3D Structure for HMDB0253485 (Ingenol mebutate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra