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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:44:11 UTC

Update Date

2021-09-26 23:02:14 UTC

HMDB ID

HMDB0250641

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyclocaric acid A

Description

1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid 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 ). Cyclocaric acid a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cyclocaric acid A 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


  Mrv1533004181500212D          

 33 38  0  0  0  0            999 V2000
   -0.5623   -3.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362   -3.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068   -4.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715   -5.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -5.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -5.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -5.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -5.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -5.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -4.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -3.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5214   -3.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997   -4.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209   -4.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853   -3.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4635   -3.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -4.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8708   -5.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1205   -4.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9834   -5.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2992   -4.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562   -5.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -4.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -4.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -3.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -5.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -6.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -6.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  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
 21 22  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
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  9 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END

HMDB0250641
     RDKit          3D
Cyclocaric acid A
 79 84  0  0  0  0  0  0  0  0999 V2000
    5.4911    1.2610   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    1.3429    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    2.5907    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212    0.1470    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.6939    1.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -1.0052    0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.9007   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1643   -2.4071    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -2.2693   -1.6819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.7699    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -2.0324   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -0.7647   -0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247   -0.9315   -2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599    0.3100   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804    1.1920    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    1.2189    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.1806    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0190    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864    0.7734    2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -1.3267    1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.5680    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -0.3161    0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5815   -0.2920   -0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6062    0.1016   -1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    0.7852   -0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    2.1008    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116    0.8390   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    0.7143   -1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978    0.5443   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.5788   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.8311   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8464    0.2640   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182    1.4657    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    1.6345   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.9543   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8675    0.2398   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    3.4810    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5947    2.4302    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426    2.7474    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.4962    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769   -0.4839    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309   -0.3304    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -1.6849    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -3.2460   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -2.7749    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526   -1.3242    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2356   -2.5632    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045   -2.7787   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -2.0233   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -0.4330   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212   -0.5809   -3.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503    1.9771    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.4603    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    2.0105    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8434   -0.8123    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.5675    2.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.8495    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.3601    3.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -2.1954    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -1.5295    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2883   -2.2819    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489   -2.1133   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9253   -0.0162    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180   -0.7911   -1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1114    0.7420   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2960    2.8083   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6827    1.9398    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3350    2.4752    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537    1.9054    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788   -0.0498   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.6755   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977    0.2772   -2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337    1.4750   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -1.8027   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1174   -1.8907   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -2.7714   -0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.3665   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    1.4219    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    2.4186    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
 25 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
M  END


  Mrv1533004181500212D          

 33 38  0  0  0  0            999 V2000
   -0.5623   -3.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362   -3.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068   -4.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715   -5.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -5.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -5.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -5.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -5.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -5.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -4.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -3.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5214   -3.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997   -4.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209   -4.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853   -3.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4635   -3.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -4.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8708   -5.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1205   -4.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9834   -5.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9562   -5.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -4.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -5.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -4.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -3.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -5.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -6.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -6.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  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
 21 22  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
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  9 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250641

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12COC1CCC1(C)C2CCC2(C)C1CC=C1C3CC(C)(C)CCC3(CCC21C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-25(2)13-15-30(24(31)32)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23-27(4,18-33-23)21(26)9-12-29(22,28)6/h7,20-23H,8-18H2,1-6H3,(H,31,32)

> <INCHI_KEY>
TYAXJAYEQFCSEV-UHFFFAOYSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.33136705170746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid

> <ALOGPS_LOGP>
6.61

> <JCHEM_LOGP>
6.475765848999999

> <ALOGPS_LOGS>
-6.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744259193129725

> <JCHEM_PKA_STRONGEST_BASIC>
-4.153523872129854

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
131.88909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250641
     RDKit          3D
Cyclocaric acid A
 79 84  0  0  0  0  0  0  0  0999 V2000
    5.4911    1.2610   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    1.3429    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    2.5907    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212    0.1470    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.6939    1.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -1.0052    0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.9007   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1643   -2.4071    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -2.2693   -1.6819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.7699    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -2.0324   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -0.7647   -0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247   -0.9315   -2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599    0.3100   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804    1.1920    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    1.2189    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.1806    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0190    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864    0.7734    2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -1.3267    1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.5680    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -0.3161    0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5815   -0.2920   -0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6062    0.1016   -1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    0.7852   -0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    2.1008    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116    0.8390   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    0.7143   -1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978    0.5443   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.5788   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.8311   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8464    0.2640   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182    1.4657    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    1.6345   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.9543   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8675    0.2398   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    3.4810    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5947    2.4302    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426    2.7474    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.4962    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769   -0.4839    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309   -0.3304    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -1.6849    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -3.2460   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -2.7749    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526   -1.3242    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2356   -2.5632    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045   -2.7787   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -2.0233   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -0.4330   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212   -0.5809   -3.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503    1.9771    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.4603    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    2.0105    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8434   -0.8123    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.5675    2.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.8495    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.3601    3.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -2.1954    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -1.5295    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2883   -2.2819    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489   -2.1133   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9253   -0.0162    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180   -0.7911   -1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1114    0.7420   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2960    2.8083   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6827    1.9398    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3350    2.4752    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537    1.9054    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788   -0.0498   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.6755   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977    0.2772   -2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337    1.4750   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -1.8027   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1174   -1.8907   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -2.7714   -0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.3665   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    1.4219    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    2.4186    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
 25 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
M  END

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -1.050  -6.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.441  -7.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -5.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.199  -8.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.693  -9.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.226  -9.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.119 -10.980   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.652 -10.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.293  -9.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.185 -10.688   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.400  -8.178   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.040  -6.778   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.573  -6.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.466  -7.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.999  -7.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.106  -6.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.639  -6.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.172  -6.195   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.065  -7.450   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.466  -8.090   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.826  -9.490   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.425  -8.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.169 -10.369   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.892  -8.996   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.252 -10.396   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.719 -10.542   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.826  -9.287   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.131 -10.797   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.867  -8.324   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.974  -7.069   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.586 -11.125   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.479 -12.380   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.053 -11.271   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   30                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29   31                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   19   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    9   14   28                                             
CONECT   28   27                                                            
CONECT   29   11    6   30                                                  
CONECT   30   29    2                                                       
CONECT   31    6   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0250641
HETATM    1  C1  UNL     1       5.491   1.261  -0.883  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.934   1.343   0.509  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.521   2.591   1.186  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.321   0.147   1.363  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.125  -0.694   1.718  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.303  -1.005   0.474  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.099  -1.901  -0.368  1.00  0.00           C  
HETATM    8  O1  UNL     1       5.164  -2.407   0.139  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.816  -2.269  -1.682  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.093  -1.770   0.957  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.064  -2.032  -0.111  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.599  -0.765  -0.822  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.025  -0.931  -2.271  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.360   0.310  -0.140  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.780   1.192   0.604  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.688   1.219   0.864  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.276  -0.181   0.637  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.738  -0.019   0.935  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.786   0.773   2.265  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.347  -1.327   1.251  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.727  -1.568   0.725  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.511  -0.316   0.679  1.00  0.00           C  
HETATM   23  O3  UNL     1      -6.581  -0.292  -0.247  1.00  0.00           O  
HETATM   24  C21 UNL     1      -5.606   0.102  -1.196  1.00  0.00           C  
HETATM   25  C22 UNL     1      -4.889   0.785  -0.107  1.00  0.00           C  
HETATM   26  C23 UNL     1      -5.609   2.101   0.233  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.412   0.839  -0.093  1.00  0.00           C  
HETATM   28  C25 UNL     1      -2.873   0.714  -1.468  1.00  0.00           C  
HETATM   29  C26 UNL     1      -1.398   0.544  -1.629  1.00  0.00           C  
HETATM   30  C27 UNL     1      -0.908  -0.579  -0.734  1.00  0.00           C  
HETATM   31  C28 UNL     1      -1.512  -1.831  -1.285  1.00  0.00           C  
HETATM   32  C29 UNL     1       2.846   0.264  -0.230  1.00  0.00           C  
HETATM   33  C30 UNL     1       3.418   1.466   0.543  1.00  0.00           C  
HETATM   34  H1  UNL     1       4.777   1.634  -1.665  1.00  0.00           H  
HETATM   35  H2  UNL     1       6.374   1.954  -0.971  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.868   0.240  -1.118  1.00  0.00           H  
HETATM   37  H4  UNL     1       5.376   3.481   0.546  1.00  0.00           H  
HETATM   38  H5  UNL     1       6.595   2.430   1.369  1.00  0.00           H  
HETATM   39  H6  UNL     1       5.043   2.747   2.175  1.00  0.00           H  
HETATM   40  H7  UNL     1       5.738   0.496   2.353  1.00  0.00           H  
HETATM   41  H8  UNL     1       6.077  -0.484   0.886  1.00  0.00           H  
HETATM   42  H9  UNL     1       3.531  -0.330   2.558  1.00  0.00           H  
HETATM   43  H10 UNL     1       4.536  -1.685   2.053  1.00  0.00           H  
HETATM   44  H11 UNL     1       3.611  -3.246  -1.860  1.00  0.00           H  
HETATM   45  H12 UNL     1       2.471  -2.775   1.271  1.00  0.00           H  
HETATM   46  H13 UNL     1       1.653  -1.324   1.871  1.00  0.00           H  
HETATM   47  H14 UNL     1       0.236  -2.563   0.409  1.00  0.00           H  
HETATM   48  H15 UNL     1       1.504  -2.779  -0.804  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.223  -2.023  -2.440  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.978  -0.433  -2.463  1.00  0.00           H  
HETATM   51  H18 UNL     1       0.321  -0.581  -3.015  1.00  0.00           H  
HETATM   52  H19 UNL     1       1.350   1.977   1.076  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.786   1.460   1.962  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.137   2.011   0.307  1.00  0.00           H  
HETATM   55  H22 UNL     1      -0.843  -0.812   1.442  1.00  0.00           H  
HETATM   56  H23 UNL     1      -3.828   0.567   2.660  1.00  0.00           H  
HETATM   57  H24 UNL     1      -2.761   1.850   2.100  1.00  0.00           H  
HETATM   58  H25 UNL     1      -2.115   0.360   3.015  1.00  0.00           H  
HETATM   59  H26 UNL     1      -2.718  -2.195   0.929  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.416  -1.529   2.369  1.00  0.00           H  
HETATM   61  H28 UNL     1      -5.288  -2.282   1.399  1.00  0.00           H  
HETATM   62  H29 UNL     1      -4.649  -2.113  -0.229  1.00  0.00           H  
HETATM   63  H30 UNL     1      -5.925  -0.016   1.661  1.00  0.00           H  
HETATM   64  H31 UNL     1      -5.218  -0.791  -1.668  1.00  0.00           H  
HETATM   65  H32 UNL     1      -6.111   0.742  -1.957  1.00  0.00           H  
HETATM   66  H33 UNL     1      -5.296   2.808  -0.590  1.00  0.00           H  
HETATM   67  H34 UNL     1      -6.683   1.940   0.090  1.00  0.00           H  
HETATM   68  H35 UNL     1      -5.335   2.475   1.221  1.00  0.00           H  
HETATM   69  H36 UNL     1      -3.154   1.905   0.207  1.00  0.00           H  
HETATM   70  H37 UNL     1      -3.379  -0.050  -2.093  1.00  0.00           H  
HETATM   71  H38 UNL     1      -3.121   1.675  -2.022  1.00  0.00           H  
HETATM   72  H39 UNL     1      -1.298   0.277  -2.734  1.00  0.00           H  
HETATM   73  H40 UNL     1      -0.834   1.475  -1.547  1.00  0.00           H  
HETATM   74  H41 UNL     1      -2.603  -1.803  -1.425  1.00  0.00           H  
HETATM   75  H42 UNL     1      -1.117  -1.891  -2.349  1.00  0.00           H  
HETATM   76  H43 UNL     1      -1.243  -2.771  -0.838  1.00  0.00           H  
HETATM   77  H44 UNL     1       3.259   0.366  -1.235  1.00  0.00           H  
HETATM   78  H45 UNL     1       3.145   1.422   1.620  1.00  0.00           H  
HETATM   79  H46 UNL     1       3.095   2.419   0.126  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   33
CONECT    3   37   38   39
CONECT    4    5   40   41
CONECT    5    6   42   43
CONECT    6    7   10   32
CONECT    7    8    8    9
CONECT    9   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   14   30
CONECT   13   49   50   51
CONECT   14   15   15   32
CONECT   15   16   52
CONECT   16   17   53   54
CONECT   17   18   30   55
CONECT   18   19   20   27
CONECT   19   56   57   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   25   63
CONECT   23   24
CONECT   24   25   64   65
CONECT   25   26   27
CONECT   26   66   67   68
CONECT   27   28   69
CONECT   28   29   70   71
CONECT   29   30   72   73
CONECT   30   31
CONECT   31   74   75   76
CONECT   32   33   77
CONECT   33   78   79
END

HMDB0250641
     RDKit          3D
Cyclocaric acid A
 79 84  0  0  0  0  0  0  0  0999 V2000
    5.4911    1.2610   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    1.3429    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    2.5907    1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212    0.1470    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.6939    1.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -1.0052    0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.9007   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1643   -2.4071    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -2.2693   -1.6819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.7699    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -2.0324   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -0.7647   -0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247   -0.9315   -2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599    0.3100   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804    1.1920    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    1.2189    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.1806    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0190    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864    0.7734    2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -1.3267    1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -1.5680    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -0.3161    0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5815   -0.2920   -0.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6062    0.1016   -1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    0.7852   -0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    2.1008    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116    0.8390   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    0.7143   -1.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978    0.5443   -1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.5788   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.8311   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8464    0.2640   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182    1.4657    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    1.6345   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.9543   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8675    0.2398   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    3.4810    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5947    2.4302    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426    2.7474    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382    0.4962    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0769   -0.4839    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309   -0.3304    2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -1.6849    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -3.2460   -1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -2.7749    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526   -1.3242    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2356   -2.5632    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045   -2.7787   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -2.0233   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -0.4330   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212   -0.5809   -3.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503    1.9771    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.4603    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    2.0105    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8434   -0.8123    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.5675    2.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.8495    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.3601    3.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -2.1954    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -1.5295    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2883   -2.2819    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6489   -2.1133   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9253   -0.0162    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180   -0.7911   -1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1114    0.7420   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2960    2.8083   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6827    1.9398    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3350    2.4752    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537    1.9054    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788   -0.0498   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206    1.6755   -2.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977    0.2772   -2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337    1.4750   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -1.8027   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1174   -1.8907   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -2.7714   -0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.3665   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    1.4219    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    2.4186    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
 25 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,8,8,15,21-Hexamethyl-19-oxahexacyclo[12.10.0.0,.0,.0,.0,]tetracos-11-ene-5-carboxylate	Generator
1,2,8,8,15,21-Hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylate	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Molecular Weight

454.695

Monoisotopic Molecular Weight

454.344695341

IUPAC Name

1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid

Traditional Name

1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²².0¹⁸,²¹]tetracos-11-ene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12COC1CCC1(C)C2CCC2(C)C1CC=C1C3CC(C)(C)CCC3(CCC21C)C(O)=O

InChI Identifier

InChI=1S/C30H46O3/c1-25(2)13-15-30(24(31)32)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23-27(4,18-33-23)21(26)9-12-29(22,28)6/h7,20-23H,8-18H2,1-6H3,(H,31,32)

InChI Key

TYAXJAYEQFCSEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxetane
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	6.61	ALOGPS
logP	6.48	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.89 m³·mol⁻¹	ChemAxon
Polarizability	54.33 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	242.314	30932474
DeepCCS	[M+Na]+	217.542	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclocaric acid A	CC12COC1CCC1(C)C2CCC2(C)C1CC=C1C3CC(C)(C)CCC3(CCC21C)C(O)=O	3328.0	Standard polar	33892256
Cyclocaric acid A	CC12COC1CCC1(C)C2CCC2(C)C1CC=C1C3CC(C)(C)CCC3(CCC21C)C(O)=O	3581.8	Standard non polar	33892256
Cyclocaric acid A	CC12COC1CCC1(C)C2CCC2(C)C1CC=C1C3CC(C)(C)CCC3(CCC21C)C(O)=O	3684.9	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 - Cyclocaric acid A GC-MS (Non-derivatized) - 70eV, Positive	splash10-009i-0031900000-64918ed5545530fb4733	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocaric acid A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocaric acid A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocaric acid A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Cyclocaric acid A 10V, Positive-QTOF	splash10-0a4i-0000900000-3751e3b37e01361ae90f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocaric acid A 20V, Positive-QTOF	splash10-000i-0000900000-3e2969d0f33b6e54ab3e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocaric acid A 40V, Positive-QTOF	splash10-0080-0940000000-21ad989d0b867cd07383	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocaric acid A 10V, Negative-QTOF	splash10-0udi-0000900000-896a352facf680cb901f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocaric acid A 20V, Negative-QTOF	splash10-0udi-0000900000-896a352facf680cb901f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocaric acid A 40V, Negative-QTOF	splash10-0udi-0000900000-9da0341b6f5f5e69a5ff	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Cyclocaric acid A (HMDB0250641)

MOL for HMDB0250641 (Cyclocaric acid A)

3D MOL for HMDB0250641 (Cyclocaric acid A)

3D SDF for HMDB0250641 (Cyclocaric acid A)

3D-SDF for HMDB0250641 (Cyclocaric acid A)

PDB for HMDB0250641 (Cyclocaric acid A)

3D PDB for HMDB0250641 (Cyclocaric acid A)

SMILES for HMDB0250641 (Cyclocaric acid A)

INCHI for HMDB0250641 (Cyclocaric acid A)

Structure for HMDB0250641 (Cyclocaric acid A)

3D Structure for HMDB0250641 (Cyclocaric acid A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra