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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-04 16:11:35 UTC

Update Date

2022-03-07 02:49:34 UTC

HMDB ID

HMDB0006927

Secondary Accession Numbers

HMDB06927

Metabolite Identification

Common Name

4a-Methylzymosterol-4-carboxylic acid

Description

2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate, also known as 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid or 5-formyl-3-hydroxy-2-methylisonicotinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate is a moderately basic compound (based on its pKa). In humans, 2-methyl-3-hydroxy-5-formylpyridine-4-carboxylate is involved in the metabolic disorder called the hypophosphatasia pathway. A pyridinemonocarboxylic acid that is pyridine-4-carboxylic acid substituted by a methyl group, hydroxy group and formyl group at positions 2,3 and 5, respectively.

Structure

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


  Mrv1652309042000332D          

 32 35  0  0  1  0            999 V2000
   15.2361   -6.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8427   -6.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9012   -8.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6358   -9.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4685  -10.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5982  -13.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4773   -7.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2654   -7.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2947   -8.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413  -11.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8673  -10.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4450  -10.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3672  -12.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1426   -9.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1203  -11.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8167   -9.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7944  -10.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4481   -6.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5066   -8.6967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9664  -11.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3239   -9.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6405  -10.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2175  -10.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182  -12.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1952  -12.2045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4198  -13.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5656   -9.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5433  -11.2532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9441  -12.5504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5211  -12.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738  -13.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2414  -13.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 18  1  0  0  0  0
 19  3  1  1  0  0  0
 27  4  1  1  0  0  0
 28  5  1  1  0  0  0
 29  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 13  1  0  0  0  0
 11 21  1  0  0  0  0
 11 12  1  0  0  0  0
 12 22  1  0  0  0  0
 24 13  1  0  0  0  0
 14 23  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 25  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 27  1  0  0  0  0
 22 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  1  1  0  0  0
 25 29  1  0  0  0  0
 26 29  1  0  0  0  0
 26 31  1  0  0  0  0
 26 32  2  0  0  0  0
M  END

HMDB0006927
     RDKit          3D
4a-Methylzymosterol-4-carboxylic acid
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.3561    0.2247    1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8598   -0.7494    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7803   -1.8389    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6299   -0.6225    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7170    0.4480    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    1.3393   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.8225   -1.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1917    2.0434   -2.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309   -0.0611   -1.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -1.4212   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -1.9572   -0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -0.8349   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -0.7404   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.4676   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.7373   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213    1.4994   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.3975   -0.5077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1524    0.4667    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.4530    0.4749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9691    0.0051    1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.8025    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6587    1.9657   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7780    0.9851   -0.3744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2240    1.3809    0.9066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.4360   -0.3207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9447   -1.0891    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8492   -1.0947   -1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1083   -1.5900   -2.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2200   -1.1676   -1.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.5410   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -1.9434   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -1.9927    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3744    1.2323    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.0020    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    0.2992    2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5103   -1.3820   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664   -2.2611    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -2.6462    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -1.3486   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    0.0880    1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.1379    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    2.2725    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1952    1.7795   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505    0.2575   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.8340   -2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    2.2091   -2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.9678   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9540   -0.3101   -2.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -2.1171   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.4858    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -2.8271   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -2.3278    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -0.8380   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.3099   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7272    2.3443    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419    1.2345   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261    2.4734   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.4775    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.2398    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.7382    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -0.0437    2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495    0.7531    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499   -0.9462    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    2.6472    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.9487    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825    2.9703   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.7952   -1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6525    1.1237   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.3126    0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0574   -0.9806    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742   -2.1511    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7695   -0.4725    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6048   -1.9989   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.2571   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -2.5383   -1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -2.5108    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3434   -2.8312   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -2.1732    1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  6
 27 28  2  0
 27 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 17  9  1  0
 30 19  1  0
 17 12  1  0
 32 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  6
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 29 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
M  END


  Mrv1652309042000332D          

 32 35  0  0  1  0            999 V2000
   15.2361   -6.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8427   -6.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9012   -8.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6358   -9.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4685  -10.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5982  -13.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4773   -7.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2654   -7.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2947   -8.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413  -11.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8673  -10.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4450  -10.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3672  -12.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1426   -9.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1203  -11.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8167   -9.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7944  -10.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4481   -6.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5066   -8.6967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9664  -11.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3239   -9.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6405  -10.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2175  -10.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182  -12.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1952  -12.2045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4198  -13.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5656   -9.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5433  -11.2532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9441  -12.5504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5211  -12.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738  -13.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2414  -13.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 18  1  0  0  0  0
 19  3  1  1  0  0  0
 27  4  1  1  0  0  0
 28  5  1  1  0  0  0
 29  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 13  1  0  0  0  0
 11 21  1  0  0  0  0
 11 12  1  0  0  0  0
 12 22  1  0  0  0  0
 24 13  1  0  0  0  0
 14 23  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 25  1  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
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 22 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  1  1  0  0  0
 25 29  1  0  0  0  0
 26 29  1  0  0  0  0
 26 31  1  0  0  0  0
 26 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006927

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24?,25-,27+,28+,29-/m0/s1

> <INCHI_KEY>
MYWAIWDQTCHPTH-IUGQOUSLSA-N

> <FORMULA>
C29H46O3

> <MOLECULAR_WEIGHT>
442.6737

> <EXACT_MASS>
442.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.537824186578064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

> <ALOGPS_LOGP>
6.64

> <JCHEM_LOGP>
6.598317999999999

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.716008813949259

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590055980466473

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0380298101870595

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
131.7868

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006927
     RDKit          3D
4a-Methylzymosterol-4-carboxylic acid
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.3561    0.2247    1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8598   -0.7494    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7803   -1.8389    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6299   -0.6225    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7170    0.4480    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    1.3393   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.8225   -1.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1917    2.0434   -2.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309   -0.0611   -1.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -1.4212   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -1.9572   -0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -0.8349   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -0.7404   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.4676   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.7373   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213    1.4994   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.3975   -0.5077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1524    0.4667    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.4530    0.4749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9691    0.0051    1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.8025    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6587    1.9657   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7780    0.9851   -0.3744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2240    1.3809    0.9066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.4360   -0.3207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9447   -1.0891    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8492   -1.0947   -1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1083   -1.5900   -2.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2200   -1.1676   -1.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.5410   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -1.9434   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -1.9927    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3744    1.2323    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.0020    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    0.2992    2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5103   -1.3820   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664   -2.2611    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -2.6462    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -1.3486   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    0.0880    1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.1379    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    2.2725    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1952    1.7795   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505    0.2575   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.8340   -2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    2.2091   -2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.9678   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9540   -0.3101   -2.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -2.1171   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.4858    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -2.8271   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -2.3278    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -0.8380   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.3099   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7272    2.3443    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419    1.2345   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261    2.4734   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.4775    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.2398    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.7382    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -0.0437    2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495    0.7531    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499   -0.9462    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    2.6472    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.9487    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825    2.9703   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.7952   -1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6525    1.1237   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.3126    0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0574   -0.9806    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742   -2.1511    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7695   -0.4725    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6048   -1.9989   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.2571   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -2.5383   -1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -2.5108    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3434   -2.8312   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -2.1732    1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  6
 27 28  2  0
 27 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 17  9  1  0
 30 19  1  0
 17 12  1  0
 32 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  6
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 29 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      28.441 -11.864   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.840 -11.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.216 -15.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.720 -16.808   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.675 -19.472   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.050 -24.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.158 -14.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.629 -13.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.817 -15.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.610 -22.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.019 -18.894   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.231 -20.217   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.352 -23.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.933 -18.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.158 -21.248   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.191 -17.697   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.416 -20.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.970 -12.319   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.346 -16.234   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.471 -20.764   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.005 -17.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.729 -19.876   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.073 -20.118   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.954 -22.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.298 -22.782   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.584 -24.686   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.589 -18.342   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.814 -21.006   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.696 -23.427   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.039 -23.670   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      16.938 -26.084   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      19.117 -24.546   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    8    9                                                       
CONECT    8    7   18                                                       
CONECT    9    7   19                                                       
CONECT   10   20   13                                                       
CONECT   11   21   12                                                       
CONECT   12   11   22                                                       
CONECT   13   10   24                                                       
CONECT   14   23   16                                                       
CONECT   15   17   25                                                       
CONECT   16   14   27                                                       
CONECT   17   15   28                                                       
CONECT   18    1    2    8                                                  
CONECT   19    3    9   21                                                  
CONECT   20   10   22   23                                                  
CONECT   21   11   19   27                                                  
CONECT   22   12   20   27                                                  
CONECT   23   14   20   28                                                  
CONECT   24   13   28   29                                                  
CONECT   25   15   30   29                                                  
CONECT   26   29   31   32                                                  
CONECT   27    4   16   21   22                                             
CONECT   28    5   17   23   24                                             
CONECT   29    6   24   25   26                                             
CONECT   30   25                                                            
CONECT   31   26                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0006927
HETATM    1  C1  UNL     1       7.356   0.225   1.994  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.860  -0.749   0.989  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.780  -1.839   0.563  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.630  -0.623   0.508  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.717   0.448   0.924  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.236   1.339  -0.155  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.468   0.822  -1.294  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.192   2.043  -2.201  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.331  -0.061  -1.177  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.486  -1.421  -0.565  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.051  -1.957  -0.404  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.217  -0.835  -0.851  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.121  -0.740  -0.259  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.651   0.468  -0.092  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.968   1.737  -0.416  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.321   1.499  -1.147  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.069   0.398  -0.508  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.152   0.467   0.977  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.052   0.453   0.475  1.00  0.00           C  
HETATM   20  C20 UNL     1      -2.969   0.005   1.918  1.00  0.00           C  
HETATM   21  C21 UNL     1      -3.674   1.803   0.450  1.00  0.00           C  
HETATM   22  C22 UNL     1      -4.659   1.966  -0.708  1.00  0.00           C  
HETATM   23  C23 UNL     1      -5.778   0.985  -0.374  1.00  0.00           C  
HETATM   24  O1  UNL     1      -6.224   1.381   0.907  1.00  0.00           O  
HETATM   25  C24 UNL     1      -5.287  -0.436  -0.321  1.00  0.00           C  
HETATM   26  C25 UNL     1      -5.945  -1.089   0.856  1.00  0.00           C  
HETATM   27  C26 UNL     1      -5.849  -1.095  -1.556  1.00  0.00           C  
HETATM   28  O2  UNL     1      -5.108  -1.590  -2.449  1.00  0.00           O  
HETATM   29  O3  UNL     1      -7.220  -1.168  -1.735  1.00  0.00           O  
HETATM   30  C27 UNL     1      -3.810  -0.541  -0.386  1.00  0.00           C  
HETATM   31  C28 UNL     1      -3.299  -1.943  -0.201  1.00  0.00           C  
HETATM   32  C29 UNL     1      -1.825  -1.993   0.127  1.00  0.00           C  
HETATM   33  H1  UNL     1       7.374   1.232   1.524  1.00  0.00           H  
HETATM   34  H2  UNL     1       8.402  -0.002   2.301  1.00  0.00           H  
HETATM   35  H3  UNL     1       6.698   0.299   2.887  1.00  0.00           H  
HETATM   36  H4  UNL     1       8.510  -1.382  -0.148  1.00  0.00           H  
HETATM   37  H5  UNL     1       8.366  -2.261   1.403  1.00  0.00           H  
HETATM   38  H6  UNL     1       7.273  -2.646   0.014  1.00  0.00           H  
HETATM   39  H7  UNL     1       5.312  -1.349  -0.220  1.00  0.00           H  
HETATM   40  H8  UNL     1       3.961   0.088   1.648  1.00  0.00           H  
HETATM   41  H9  UNL     1       5.343   1.138   1.623  1.00  0.00           H  
HETATM   42  H10 UNL     1       3.795   2.273   0.301  1.00  0.00           H  
HETATM   43  H11 UNL     1       5.195   1.780  -0.608  1.00  0.00           H  
HETATM   44  H12 UNL     1       4.250   0.258  -1.916  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.367   1.834  -2.908  1.00  0.00           H  
HETATM   46  H14 UNL     1       4.088   2.209  -2.837  1.00  0.00           H  
HETATM   47  H15 UNL     1       3.098   2.968  -1.618  1.00  0.00           H  
HETATM   48  H16 UNL     1       1.954  -0.310  -2.239  1.00  0.00           H  
HETATM   49  H17 UNL     1       2.964  -2.117  -1.302  1.00  0.00           H  
HETATM   50  H18 UNL     1       2.908  -1.486   0.423  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.862  -2.827  -1.081  1.00  0.00           H  
HETATM   52  H20 UNL     1       0.850  -2.328   0.610  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.139  -0.838  -1.961  1.00  0.00           H  
HETATM   54  H22 UNL     1      -1.672   2.310  -1.089  1.00  0.00           H  
HETATM   55  H23 UNL     1      -0.727   2.344   0.478  1.00  0.00           H  
HETATM   56  H24 UNL     1       0.042   1.234  -2.201  1.00  0.00           H  
HETATM   57  H25 UNL     1       0.826   2.473  -1.208  1.00  0.00           H  
HETATM   58  H26 UNL     1       1.485  -0.478   1.453  1.00  0.00           H  
HETATM   59  H27 UNL     1       1.895   1.240   1.333  1.00  0.00           H  
HETATM   60  H28 UNL     1       0.214   0.738   1.474  1.00  0.00           H  
HETATM   61  H29 UNL     1      -1.909  -0.044   2.265  1.00  0.00           H  
HETATM   62  H30 UNL     1      -3.450   0.753   2.615  1.00  0.00           H  
HETATM   63  H31 UNL     1      -3.450  -0.946   2.124  1.00  0.00           H  
HETATM   64  H32 UNL     1      -2.986   2.647   0.432  1.00  0.00           H  
HETATM   65  H33 UNL     1      -4.313   1.949   1.373  1.00  0.00           H  
HETATM   66  H34 UNL     1      -5.083   2.970  -0.659  1.00  0.00           H  
HETATM   67  H35 UNL     1      -4.210   1.795  -1.679  1.00  0.00           H  
HETATM   68  H36 UNL     1      -6.652   1.124  -1.043  1.00  0.00           H  
HETATM   69  H37 UNL     1      -7.203   1.313   0.980  1.00  0.00           H  
HETATM   70  H38 UNL     1      -7.057  -0.981   0.676  1.00  0.00           H  
HETATM   71  H39 UNL     1      -5.774  -2.151   0.978  1.00  0.00           H  
HETATM   72  H40 UNL     1      -5.770  -0.473   1.770  1.00  0.00           H  
HETATM   73  H41 UNL     1      -7.605  -1.999  -2.172  1.00  0.00           H  
HETATM   74  H42 UNL     1      -3.518  -0.257  -1.444  1.00  0.00           H  
HETATM   75  H43 UNL     1      -3.450  -2.538  -1.126  1.00  0.00           H  
HETATM   76  H44 UNL     1      -3.813  -2.511   0.602  1.00  0.00           H  
HETATM   77  H45 UNL     1      -1.343  -2.831  -0.415  1.00  0.00           H  
HETATM   78  H46 UNL     1      -1.614  -2.173   1.201  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4    4
CONECT    3   36   37   38
CONECT    4    5   39
CONECT    5    6   40   41
CONECT    6    7   42   43
CONECT    7    8    9   44
CONECT    8   45   46   47
CONECT    9   10   17   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   17   53
CONECT   13   14   14   32
CONECT   14   15   19
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18
CONECT   18   58   59   60
CONECT   19   20   21   30
CONECT   20   61   62   63
CONECT   21   22   64   65
CONECT   22   23   66   67
CONECT   23   24   25   68
CONECT   24   69
CONECT   25   26   27   30
CONECT   26   70   71   72
CONECT   27   28   28   29
CONECT   29   73
CONECT   30   31   74
CONECT   31   32   75   76
CONECT   32   77   78
END

HMDB0006927
     RDKit          3D
4a-Methylzymosterol-4-carboxylic acid
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.3561    0.2247    1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8598   -0.7494    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7803   -1.8389    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6299   -0.6225    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7170    0.4480    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    1.3393   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.8225   -1.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1917    2.0434   -2.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309   -0.0611   -1.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -1.4212   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -1.9572   -0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -0.8349   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -0.7404   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.4676   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.7373   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213    1.4994   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.3975   -0.5077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1524    0.4667    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.4530    0.4749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9691    0.0051    1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.8025    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6587    1.9657   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7780    0.9851   -0.3744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2240    1.3809    0.9066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.4360   -0.3207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9447   -1.0891    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8492   -1.0947   -1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1083   -1.5900   -2.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2200   -1.1676   -1.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.5410   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -1.9434   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -1.9927    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3744    1.2323    1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.0020    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    0.2992    2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5103   -1.3820   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664   -2.2611    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -2.6462    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -1.3486   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    0.0880    1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.1379    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    2.2725    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1952    1.7795   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505    0.2575   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.8340   -2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    2.2091   -2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.9678   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9540   -0.3101   -2.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -2.1171   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.4858    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -2.8271   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -2.3278    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -0.8380   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.3099   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7272    2.3443    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419    1.2345   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261    2.4734   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849   -0.4775    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953    1.2398    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.7382    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -0.0437    2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495    0.7531    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499   -0.9462    2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    2.6472    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129    1.9487    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825    2.9703   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.7952   -1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6525    1.1237   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.3126    0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0574   -0.9806    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742   -2.1511    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7695   -0.4725    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6048   -1.9989   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.2571   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -2.5383   -1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -2.5108    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3434   -2.8312   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -2.1732    1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  6
 27 28  2  0
 27 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 17  9  1  0
 30 19  1  0
 17 12  1  0
 32 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  6
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 29 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylic acid	ChEBI
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylic acid	ChEBI
5-Formyl-3-hydroxy-2-methylisonicotinic acid	ChEBI
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylate	Kegg
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylate	Generator
5-Formyl-3-hydroxy-2-methylisonicotinate	Generator
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid	Generator
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol	HMDB
4alpha-Methylzymosterol-4-carboxylic acid	HMDB
4a-Methylzymosterol-4-carboxylate	Generator

Chemical Formula

C₂₉H₄₆O₃

Average Molecular Weight

442.6737

Monoisotopic Molecular Weight

442.344695338

IUPAC Name

(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

Traditional Name

(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O

InChI Identifier

InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24?,25-,27+,28+,29-/m0/s1

InChI Key

MYWAIWDQTCHPTH-IUGQOUSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
3-pyridine carboxaldehyde
Aryl-aldehyde
Hydroxypyridine
Methylpyridine
Vinylogous acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Aldehyde
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:28038 )
pyridinecarbaldehyde (CHEBI:28038 )
methylpyridines (CHEBI:28038 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006927)

Source

Endogenous

Endogenous (HMDB: HMDB0006927)

Animal

Animal (HMDB: HMDB0006927)

Exogenous

Food

Food (HMDB: HMDB0006927)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Exogenous (HMDB: HMDB0006927)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006927)

Biochemical pathway

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0006927)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006927)
Steroid Biosynthesis (PathBank: SMP0087326)

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0006927)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
CHILD Syndrome (PathBank: SMP0120464)
Wolman Disease (PathBank: SMP0120576)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Lipid metabolism pathway (HMDB: HMDB0006927)

Cellular process

Cell signaling (HMDB: HMDB0006927)

Biochemical process

Lipid transport (HMDB: HMDB0006927)

Role

Biological role

Energy source (HMDB: HMDB0006927)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006927)

Physical Properties

State

Solid

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
Water Solubility	0.0022 g/L	ALOGPS
logP	6.64	ALOGPS
logP	6.6	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.79 m³·mol⁻¹	ChemAxon
Polarizability	54.54 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	208.198	31661259
DarkChem	[M-H]-	201.626	31661259
DeepCCS	[M-2H]-	240.561	30932474
DeepCCS	[M+Na]+	215.985	30932474
AllCCS	[M+H]+	213.1	32859911
AllCCS	[M+H-H2O]+	211.2	32859911
AllCCS	[M+NH4]+	214.8	32859911
AllCCS	[M+Na]+	215.2	32859911
AllCCS	[M-H]-	213.5	32859911
AllCCS	[M+Na-2H]-	215.6	32859911
AllCCS	[M+HCOO]-	218.1	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.	9.9 minutes	32390414
Predicted by Siyang on May 30, 2022	23.0443 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3534.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	536.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	281.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	551.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	913.5 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	1013.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1784.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	680.2 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	1786.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	636.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	581.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	241.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	556.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4a-Methylzymosterol-4-carboxylic acid	C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3338.6	Standard polar	33892256
4a-Methylzymosterol-4-carboxylic acid	C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3345.7	Standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid	C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O	3566.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4a-Methylzymosterol-4-carboxylic acid,1TMS,isomer #1	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O)C1CC3	3593.7	Semi standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid,1TMS,isomer #2	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(=O)O[Si](C)(C)C)C1CC3	3509.0	Semi standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid,2TMS,isomer #1	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O[Si](C)(C)C)C1CC3	3515.8	Semi standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid,1TBDMS,isomer #1	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O)C1CC3	3808.6	Semi standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid,1TBDMS,isomer #2	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	3760.9	Semi standard non polar	33892256
4a-Methylzymosterol-4-carboxylic acid,2TBDMS,isomer #1	CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC3	4002.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2009500000-d95a96ec50d214c4a7ad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3001290000-49cf623a8c01d727af89	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 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 - 4a-Methylzymosterol-4-carboxylic acid 10V, Positive-QTOF	splash10-004i-0003900000-ede2074ebef5c7b4f5ef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Positive-QTOF	splash10-056r-3009600000-668782b6420b243b39ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Positive-QTOF	splash10-0ar9-4129200000-aa72815365e75b94ccbc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Negative-QTOF	splash10-0006-0003900000-8cabb8e5bbac4a6dfdf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Negative-QTOF	splash10-002e-0009500000-4c342723259093956de9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Negative-QTOF	splash10-0059-1009200000-1be86c464989109fde9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Negative-QTOF	splash10-0006-0000900000-a071385ec6b10bec9802	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Negative-QTOF	splash10-0006-0005900000-7395cb3ac36e70ff026a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Negative-QTOF	splash10-00ku-3004900000-d631319845841e3d35f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Positive-QTOF	splash10-0006-0005900000-201f4ae9e2e8593bb420	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Positive-QTOF	splash10-0gwo-4249500000-9b29d5f0aa9ef228b757	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Positive-QTOF	splash10-0a4l-9778000000-4438f729f0f6c14e77d9	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

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

FDB024160

KNApSAcK ID

Not Available

Chemspider ID

389728

KEGG Compound ID

C06050

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440898

PDB ID

Not Available

ChEBI ID

28038

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

Not Available

Enzymes

Enzyme Details

1. Methylsterol monooxygenase 1

General function:: Involved in iron ion binding
Specific function:: Not Available
Gene Name:: MSMO1
Uniprot ID:: Q15800
Molecular weight:: 19470.325

Enzyme Details

2. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: Not Available
Gene Name:: NSDHL
Uniprot ID:: Q15738
Molecular weight:: 41899.99

Enzyme Details

3. 3-keto-steroid reductase

General function:: Involved in oxidoreductase activity
Specific function:: Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:: HSD17B7
Uniprot ID:: P56937
Molecular weight:: 38205.77

Showing metabocard for 4a-Methylzymosterol-4-carboxylic acid (HMDB0006927)

MOL for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

3D MOL for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

3D SDF for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

3D-SDF for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

PDB for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

3D PDB for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

SMILES for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

INCHI for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

Structure for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

3D Structure for HMDB0006927 (4a-Methylzymosterol-4-carboxylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes