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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:02:30 UTC

Update Date

2022-03-07 02:55:53 UTC

HMDB ID

HMDB0038705

Secondary Accession Numbers

HMDB38705

Metabolite Identification

Common Name

Macrocarpal C

Description

Macrocarpal C belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Based on a literature review a small amount of articles have been published on Macrocarpal C.

Structure

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


  Mrv0541 02241216212D          

 33 36  0  0  0  0            999 V2000
   -0.1245    1.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414   -0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    1.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    0.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417    1.2082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7077   -1.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9584   -1.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080   -0.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245   -0.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    0.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8747   -1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750   -1.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1252   -2.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085   -1.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -0.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -2.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248   -2.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4581    2.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083    2.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747    2.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 32  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 29  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0038705
     RDKit          3D
Macrocarpal C
 71 74  0  0  0  0  0  0  0  0999 V2000
   -4.1138   -1.3869   -2.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0948   -1.7198   -1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -2.8806   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167   -2.3761    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -0.9918    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969   -1.0182    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -0.8355   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -0.8925   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2336    0.5135   -2.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    1.3936   -1.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599    0.3712   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.0020   -2.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.8271   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    1.9984   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    3.3198   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4152    3.8884    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    4.3221   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -0.1672    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -0.2685    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1058    0.4225    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -1.0556    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.1594    3.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.5192    4.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -1.7762    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -2.5356    2.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165   -1.7094    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -2.4340   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713   -3.1298   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.8979   -0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9074   -1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948   -0.3929    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047   -1.1249    3.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    1.0542    1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -0.5746   -3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332   -1.9490   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -3.6407   -0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159   -3.3523   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -3.0907    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -2.3115    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144   -0.3306    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391   -2.0696    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -1.6759   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -1.3624   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.6614   -3.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    0.9176   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    1.9560   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572    2.0953   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -1.0967   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330    0.5581   -2.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    0.1337   -3.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    1.1871    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    1.7379   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    2.2050    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041    3.4092   -1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    3.1249    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    4.5502    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491    4.4950   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    4.5504   -2.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584    5.2538   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874    3.9046   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3786   -3.1208    2.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707   -2.4064   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -1.3244   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5869   -2.1052    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
  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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 21 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 26 29  2  0
 29 30  1  0
  6 31  1  0
 31 32  1  0
 31 33  1  0
  8  2  1  0
 29 18  1  0
 31  5  1  0
 11  7  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  6 41  1  0
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 27 64  1  0
 30 65  1  0
 32 66  1  0
 32 67  1  0
 32 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END


  Mrv0541 02241216212D          

 33 36  0  0  0  0            999 V2000
   -0.1245    1.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414   -0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    1.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    0.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081    0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417    1.2082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7077   -1.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9584   -1.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080   -0.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245   -0.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  7  1  0  0  0  0
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  4 13  1  0  0  0  0
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  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
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 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 29  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038705

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O5/c1-14(2)11-20(21-25(32)17(12-29)24(31)18(13-30)26(21)33)28(6)10-9-16-15(3)7-8-19-23(22(16)28)27(19,4)5/h12-14,16,19-20,22-23,31-33H,3,7-11H2,1-2,4-6H3

> <INCHI_KEY>
IEWHEHWXBLPFER-UHFFFAOYSA-N

> <FORMULA>
C28H38O5

> <MOLECULAR_WEIGHT>
454.5983

> <EXACT_MASS>
454.271924326

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
50.255273881290634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-decahydro-1H-cyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
8.601967837666665

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.756789484195622

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.677217991209816

> <JCHEM_PKA_STRONGEST_BASIC>
-5.378766134744457

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
131.27639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-octahydrocyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038705
     RDKit          3D
Macrocarpal C
 71 74  0  0  0  0  0  0  0  0999 V2000
   -4.1138   -1.3869   -2.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0948   -1.7198   -1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -2.8806   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167   -2.3761    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -0.9918    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969   -1.0182    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -0.8355   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -0.8925   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2336    0.5135   -2.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    1.3936   -1.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599    0.3712   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.0020   -2.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.8271   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    1.9984   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    3.3198   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4152    3.8884    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    4.3221   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -0.1672    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -0.2685    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1058    0.4225    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -1.0556    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.1594    3.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.5192    4.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -1.7762    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -2.5356    2.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165   -1.7094    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -2.4340   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713   -3.1298   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.8979   -0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9074   -1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948   -0.3929    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047   -1.1249    3.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    1.0542    1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -0.5746   -3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332   -1.9490   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -3.6407   -0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159   -3.3523   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -3.0907    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -2.3115    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144   -0.3306    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391   -2.0696    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -1.6759   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -1.3624   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.6614   -3.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    0.9176   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    1.9560   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572    2.0953   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -1.0967   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330    0.5581   -2.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    0.1337   -3.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    1.1871    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    1.7379   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    2.2050    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041    3.4092   -1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    3.1249    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    4.5502    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491    4.4950   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    4.5504   -2.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584    5.2538   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874    3.9046   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052    1.0542    2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -1.7850    4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3786   -3.1208    2.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707   -2.4064   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -1.3244   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5869   -2.1052    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1522   -1.3132    3.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -0.5470    3.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    1.1716    2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593    1.3839    2.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9550    1.7764    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 21 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 26 29  2  0
 29 30  1  0
  6 31  1  0
 31 32  1  0
 31 33  1  0
  8  2  1  0
 29 18  1  0
 31  5  1  0
 11  7  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 17 60  1  0
 20 61  1  0
 22 62  1  0
 25 63  1  0
 27 64  1  0
 30 65  1  0
 32 66  1  0
 32 67  1  0
 32 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.232   2.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.079   1.321   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.478   0.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.944  -0.855   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.166  -2.099   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.567   3.188   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.567   1.633   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.122   1.321   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.211   2.410   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.611   2.255   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.054  -3.344   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.656  -2.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.344  -1.321   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.588  -0.234   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.988  -0.699   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.232  -0.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.321   0.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.255   1.478   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.656   1.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.656  -0.544   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.255  -1.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.633  -2.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.567  -3.656   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.967  -3.811   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.056  -2.877   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.056  -1.321   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.611  -1.633   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.478  -5.366   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.166  -3.811   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.389  -4.122   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.855   5.366   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.389   4.277   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.633   5.056   0.000  0.00  0.00           C+0
CONECT    1    2   32                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    3    6    8                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13                                                       
CONECT   13    4   12   14                                                  
CONECT   14    8   13   15                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    2   16   18   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   17   20   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   20   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   22   23   28   30                                             
CONECT   30   29                                                            
CONECT   31   32                                                            
CONECT   32    1   31   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0038705
HETATM    1  C1  UNL     1      -4.114  -1.387  -2.403  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.095  -1.720  -1.645  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.357  -2.881  -0.728  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.417  -2.376   0.725  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.858  -0.992   0.673  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.297  -1.018   0.590  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.891  -0.835  -0.763  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.905  -0.892  -1.863  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.234   0.513  -2.215  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.102   1.394  -1.713  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.060   0.371  -1.250  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.509  -0.002  -2.574  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.872   0.827  -0.227  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.776   1.998  -0.552  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.206   3.320  -0.866  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.415   3.888   0.329  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.330   4.322  -1.183  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.839  -0.167   0.374  1.00  0.00           C  
HETATM   19  C19 UNL     1       1.942  -0.268   1.778  1.00  0.00           C  
HETATM   20  O1  UNL     1       1.106   0.422   2.619  1.00  0.00           O  
HETATM   21  C20 UNL     1       2.883  -1.056   2.400  1.00  0.00           C  
HETATM   22  C21 UNL     1       2.913  -1.159   3.883  1.00  0.00           C  
HETATM   23  O2  UNL     1       2.070  -0.519   4.540  1.00  0.00           O  
HETATM   24  C22 UNL     1       3.769  -1.776   1.633  1.00  0.00           C  
HETATM   25  O3  UNL     1       4.677  -2.536   2.331  1.00  0.00           O  
HETATM   26  C23 UNL     1       3.716  -1.709   0.273  1.00  0.00           C  
HETATM   27  C24 UNL     1       4.680  -2.434  -0.576  1.00  0.00           C  
HETATM   28  O4  UNL     1       5.571  -3.130  -0.066  1.00  0.00           O  
HETATM   29  C25 UNL     1       2.744  -0.898  -0.346  1.00  0.00           C  
HETATM   30  O5  UNL     1       2.812  -0.907  -1.705  1.00  0.00           O  
HETATM   31  C26 UNL     1      -1.995  -0.393   1.667  1.00  0.00           C  
HETATM   32  C27 UNL     1      -2.105  -1.125   3.031  1.00  0.00           C  
HETATM   33  C28 UNL     1      -2.299   1.054   1.946  1.00  0.00           C  
HETATM   34  H1  UNL     1      -4.117  -0.575  -3.128  1.00  0.00           H  
HETATM   35  H2  UNL     1      -5.033  -1.949  -2.318  1.00  0.00           H  
HETATM   36  H3  UNL     1      -2.561  -3.641  -0.870  1.00  0.00           H  
HETATM   37  H4  UNL     1      -4.316  -3.352  -0.928  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.878  -3.091   1.365  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.460  -2.312   1.085  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.414  -0.331   0.022  1.00  0.00           H  
HETATM   41  H8  UNL     1      -0.939  -2.070   0.971  1.00  0.00           H  
HETATM   42  H9  UNL     1      -0.159  -1.676  -1.039  1.00  0.00           H  
HETATM   43  H10 UNL     1      -1.451  -1.362  -2.806  1.00  0.00           H  
HETATM   44  H11 UNL     1      -2.262   0.661  -3.347  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.190   0.918  -1.889  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.706   1.956  -2.603  1.00  0.00           H  
HETATM   47  H14 UNL     1      -1.457   2.095  -1.009  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.658  -1.097  -2.653  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.333   0.558  -2.974  1.00  0.00           H  
HETATM   50  H17 UNL     1      -0.303   0.134  -3.406  1.00  0.00           H  
HETATM   51  H18 UNL     1       0.259   1.187   0.626  1.00  0.00           H  
HETATM   52  H19 UNL     1       2.549   1.738  -1.299  1.00  0.00           H  
HETATM   53  H20 UNL     1       2.305   2.205   0.454  1.00  0.00           H  
HETATM   54  H21 UNL     1       0.504   3.409  -1.702  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.075   3.125   1.027  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.140   4.550   0.897  1.00  0.00           H  
HETATM   57  H24 UNL     1      -0.449   4.495  -0.006  1.00  0.00           H  
HETATM   58  H25 UNL     1       2.377   4.550  -2.252  1.00  0.00           H  
HETATM   59  H26 UNL     1       2.158   5.254  -0.636  1.00  0.00           H  
HETATM   60  H27 UNL     1       3.287   3.905  -0.829  1.00  0.00           H  
HETATM   61  H28 UNL     1       0.405   1.054   2.520  1.00  0.00           H  
HETATM   62  H29 UNL     1       3.664  -1.785   4.344  1.00  0.00           H  
HETATM   63  H30 UNL     1       5.379  -3.121   2.028  1.00  0.00           H  
HETATM   64  H31 UNL     1       4.671  -2.406  -1.647  1.00  0.00           H  
HETATM   65  H32 UNL     1       3.352  -1.324  -2.389  1.00  0.00           H  
HETATM   66  H33 UNL     1      -1.587  -2.105   2.954  1.00  0.00           H  
HETATM   67  H34 UNL     1      -3.152  -1.313   3.300  1.00  0.00           H  
HETATM   68  H35 UNL     1      -1.576  -0.547   3.810  1.00  0.00           H  
HETATM   69  H36 UNL     1      -3.392   1.172   2.065  1.00  0.00           H  
HETATM   70  H37 UNL     1      -1.859   1.384   2.933  1.00  0.00           H  
HETATM   71  H38 UNL     1      -1.955   1.776   1.209  1.00  0.00           H  
CONECT    1    2    2   34   35
CONECT    2    3    8
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6   31   40
CONECT    6    7   31   41
CONECT    7    8   11   42
CONECT    8    9   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   13
CONECT   12   48   49   50
CONECT   13   14   18   51
CONECT   14   15   52   53
CONECT   15   16   17   54
CONECT   16   55   56   57
CONECT   17   58   59   60
CONECT   18   19   19   29
CONECT   19   20   21
CONECT   20   61
CONECT   21   22   24   24
CONECT   22   23   23   62
CONECT   24   25   26
CONECT   25   63
CONECT   26   27   29   29
CONECT   27   28   28   64
CONECT   29   30
CONECT   30   65
CONECT   31   32   33
CONECT   32   66   67   68
CONECT   33   69   70   71
END

HMDB0038705
     RDKit          3D
Macrocarpal C
 71 74  0  0  0  0  0  0  0  0999 V2000
   -4.1138   -1.3869   -2.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0948   -1.7198   -1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -2.8806   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167   -2.3761    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -0.9918    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969   -1.0182    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -0.8355   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -0.8925   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2336    0.5135   -2.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    1.3936   -1.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599    0.3712   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.0020   -2.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.8271   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    1.9984   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    3.3198   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4152    3.8884    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    4.3221   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -0.1672    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -0.2685    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1058    0.4225    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -1.0556    2.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.1594    3.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -0.5192    4.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -1.7762    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -2.5356    2.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165   -1.7094    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -2.4340   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713   -3.1298   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.8979   -0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9074   -1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948   -0.3929    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047   -1.1249    3.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    1.0542    1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -0.5746   -3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332   -1.9490   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -3.6407   -0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159   -3.3523   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -3.0907    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -2.3115    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144   -0.3306    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391   -2.0696    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -1.6759   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -1.3624   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    0.6614   -3.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    0.9176   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    1.9560   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572    2.0953   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -1.0967   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330    0.5581   -2.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    0.1337   -3.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    1.1871    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    1.7379   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    2.2050    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041    3.4092   -1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    3.1249    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    4.5502    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491    4.4950   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    4.5504   -2.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584    5.2538   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874    3.9046   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052    1.0542    2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -1.7850    4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3786   -3.1208    2.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707   -2.4064   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -1.3244   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5869   -2.1052    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1522   -1.3132    3.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -0.5470    3.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    1.1716    2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593    1.3839    2.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9550    1.7764    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 13 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 21 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 26 29  2  0
 29 30  1  0
  6 31  1  0
 31 32  1  0
 31 33  1  0
  8  2  1  0
 29 18  1  0
 31  5  1  0
 11  7  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 17 60  1  0
 20 61  1  0
 22 62  1  0
 25 63  1  0
 27 64  1  0
 30 65  1  0
 32 66  1  0
 32 67  1  0
 32 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₅

Average Molecular Weight

454.5983

Monoisotopic Molecular Weight

454.271924326

IUPAC Name

2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-decahydro-1H-cyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde

Traditional Name

2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-octahydrocyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde

CAS Registry Number

142628-53-3

SMILES

CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C

InChI Identifier

InChI=1S/C28H38O5/c1-14(2)11-20(21-25(32)17(12-29)24(31)18(13-30)26(21)33)28(6)10-9-16-15(3)7-8-19-23(22(16)28)27(19,4)5/h12-14,16,19-20,22-23,31-33H,3,7-11H2,1-2,4-6H3

InChI Key

IEWHEHWXBLPFER-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

Guaiane sesquiterpenoid
5,10-cycloaromadendrane sesquiterpenoid
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Hydroxybenzaldehyde
Benzoyl
Benzaldehyde
Aryl-aldehyde
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Polyol
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038705)

Source

Endogenous

Endogenous (HMDB: HMDB0038705)

Animal

Animal (HMDB: HMDB0038705)

Exogenous

Food

Food (HMDB: HMDB0038705)

Exogenous (HMDB: HMDB0038705)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038705)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038705)

Lipid metabolism pathway (HMDB: HMDB0038705)

Cellular process

Cell signaling (HMDB: HMDB0038705)

Biochemical process

Lipid transport (HMDB: HMDB0038705)

Role

Biological role

Energy source (HMDB: HMDB0038705)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038705)

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	1.4e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	4.79	ALOGPS
logP	8.6	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.28 m³·mol⁻¹	ChemAxon
Polarizability	50.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	201.624	31661259
DarkChem	[M-H]-	201.769	31661259
DeepCCS	[M+H]+	217.15	30932474
DeepCCS	[M-H]-	214.755	30932474
DeepCCS	[M-2H]-	247.638	30932474
DeepCCS	[M+Na]+	223.063	30932474
AllCCS	[M+H]+	208.5	32859911
AllCCS	[M+H-H2O]+	206.5	32859911
AllCCS	[M+NH4]+	210.2	32859911
AllCCS	[M+Na]+	210.7	32859911
AllCCS	[M-H]-	214.3	32859911
AllCCS	[M+Na-2H]-	215.4	32859911
AllCCS	[M+HCOO]-	216.8	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.	7.62 minutes	32390414
Predicted by Siyang on May 30, 2022	30.7089 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4412.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	990.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	364.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	487.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	818.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1413.7 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	1932.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2435.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	931.9 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	2827.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	884.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1075.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	725.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	703.5 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	18.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Macrocarpal C	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C	3790.3	Standard polar	33892256
Macrocarpal C	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C	3153.6	Standard non polar	33892256
Macrocarpal C	CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C	3509.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Macrocarpal C,1TMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C2(C)C	3462.9	Semi standard non polar	33892256
Macrocarpal C,1TMS,isomer #2	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C2(C)C	3469.2	Semi standard non polar	33892256
Macrocarpal C,2TMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C2(C)C	3500.1	Semi standard non polar	33892256
Macrocarpal C,2TMS,isomer #2	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C2(C)C	3495.1	Semi standard non polar	33892256
Macrocarpal C,3TMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C2(C)C	3538.0	Semi standard non polar	33892256
Macrocarpal C,1TBDMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C2(C)C	3688.9	Semi standard non polar	33892256
Macrocarpal C,1TBDMS,isomer #2	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C2(C)C	3698.0	Semi standard non polar	33892256
Macrocarpal C,2TBDMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C2(C)C	3935.4	Semi standard non polar	33892256
Macrocarpal C,2TBDMS,isomer #2	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C2(C)C	3937.0	Semi standard non polar	33892256
Macrocarpal C,3TBDMS,isomer #1	C=C1CCC2C(C3C1CCC3(C)C(CC(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C2(C)C	4127.3	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 - Macrocarpal C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ug1-6375900000-006a73eb3d14afae17d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal C GC-MS (3 TMS) - 70eV, Positive	splash10-0bt9-3110409000-9ccf1e9e633f5cb41715	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrocarpal C 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 - Macrocarpal C 10V, Positive-QTOF	splash10-0a4i-0010900000-908d5a0dcd19539f2c15	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 20V, Positive-QTOF	splash10-0a4i-4251900000-a5eb9e770193cd3640f7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 40V, Positive-QTOF	splash10-052r-7793600000-34a5bac00d12c03891e6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 10V, Negative-QTOF	splash10-0udi-0000900000-35d083ee7055b176839d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 20V, Negative-QTOF	splash10-0udi-0310900000-11f6e5b006e4a0f86d15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 40V, Negative-QTOF	splash10-03dr-6987500000-f3ba2a52f76bbf5df39a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 10V, Negative-QTOF	splash10-0udi-0000900000-5c49a79e6b8fb485c471	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 20V, Negative-QTOF	splash10-0f92-0207900000-b1b6c9b316512d0db8a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 40V, Negative-QTOF	splash10-0udm-3129300000-b9ad96be10c81cfb3327	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 10V, Positive-QTOF	splash10-0a4i-0140900000-3e68b25c3bbc83edde9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 20V, Positive-QTOF	splash10-015i-7118900000-5324982474d31d940336	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrocarpal C 40V, Positive-QTOF	splash10-067l-9602000000-00f0bc00a4886ebc8565	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018112

KNApSAcK ID

Not Available

Chemspider ID

8271035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10095499

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Macrocarpal C (HMDB0038705)

MOL for HMDB0038705 (Macrocarpal C)

3D MOL for HMDB0038705 (Macrocarpal C)

3D SDF for HMDB0038705 (Macrocarpal C)

3D-SDF for HMDB0038705 (Macrocarpal C)

PDB for HMDB0038705 (Macrocarpal C)

3D PDB for HMDB0038705 (Macrocarpal C)

SMILES for HMDB0038705 (Macrocarpal C)

INCHI for HMDB0038705 (Macrocarpal C)

Structure for HMDB0038705 (Macrocarpal C)

3D Structure for HMDB0038705 (Macrocarpal C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra