NP-MRD: Showing NP-Card for Protoconstipatic acid (NP0003392)

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Record Information

Version

2.0

Created at

2020-12-09 00:39:51 UTC

Updated at

2021-07-15 16:46:18 UTC

NP-MRD ID

NP0003392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protoconstipatic acid

Provided By

NPAtlas

Description

(2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Protoconstipatic acid is found in Lecanora fructulosa, Lecanora frustulosa and Unknown-fungus sp.. Based on a literature review very few articles have been published on (2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 62 62  0  0  0  0            999 V2000
   -8.5744    0.2304    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4042   -0.2396    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6720   -1.3436    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0507   -2.0669    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4482   -1.4667    0.4802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1526   -0.1781    0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1071   -0.0310   -1.0038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7290   -0.4885   -0.5435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356   -1.9044   -0.1869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4725   -2.6058    0.1082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6394   -2.1230    1.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0192   -0.8074    1.0848 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9388   -0.8297   -0.1303 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6454    0.4918   -0.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4941    0.8924    0.8350 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6031   -0.0373    1.1808 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5845   -0.2431    0.0495 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2064    1.0824   -0.3296 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1970    0.9311   -1.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.1242    0.5071    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    0.0575   -2.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5408    0.2258   -0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6279    1.6570   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0051    2.0831   -1.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2971    2.5649    0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0568    1.0587    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9735    0.5355    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8358   -2.5854   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -3.7345    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -2.0565    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169   -2.9203    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571   -0.5867    2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    0.0610    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6166   -1.7028   -0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880    0.4571   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7780    3.4698    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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
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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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  6 23  1  0  0  0  0
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 23  2  1  0  0  0  0
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 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 22 60  1  0  0  0  0
 23 61  1  6  0  0  0
 26 62  1  0  0  0  0
M  END

     RDKit          3D

 62 62  0  0  0  0  0  0  0  0999 V2000
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   -4.1071   -0.0310   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4725   -2.6058    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242117473D          

 62 62  0  0  0  0            999 V2000
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    8.2247    0.0575   -2.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5408    0.2258   -0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6279    1.6570   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0051    2.0831   -1.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2971    2.5649    0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5908    0.1757    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -2.5441   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166   -1.9793    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358   -2.5854   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -3.7345    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -2.0565    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169   -2.9203    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571   -0.5867    2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    0.0610    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2825   -0.9304   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -1.7028   -0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880    0.4571   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.2606   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.0324    1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153    1.8970    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.0420    1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    0.3644    2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0478   -0.7106   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032   -0.8820    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6940    1.5783    0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    1.7884   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    0.6807   -2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    1.9502   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0168   -1.0165   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6037    1.4945   -0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8848   -0.2381    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4261    0.5904    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9104    0.7631   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301   -0.3794   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7780    3.4698    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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
 10 11  1  0  0  0  0
 11 12  1  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
 16 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
 20 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23  2  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  6 29  1  1  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  0  0  0  0
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 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
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 19 55  1  0  0  0  0
 20 56  1  1  0  0  0
 21 57  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 22 60  1  0  0  0  0
 23 61  1  6  0  0  0
 26 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])C(=C([H])[H])C(=O)O[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O5/c1-16(22)14-12-10-8-6-4-3-5-7-9-11-13-15-18-19(20(23)24)17(2)21(25)26-18/h16,18-19,22H,2-15H2,1H3,(H,23,24)/t16-,18-,19+/m0/s1

> <INCHI_KEY>
UYUDMGMNHAKPEV-YTQUADARSA-N

> <FORMULA>
C21H36O5

> <MOLECULAR_WEIGHT>
368.514

> <EXACT_MASS>
368.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.12452746680685

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
5.466662069333332

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.683061087845683

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2400299563468415

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6252273145194094

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
101.27419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 62  0  0  0  0  0  0  0  0999 V2000
   -8.5744    0.2304    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4042   -0.2396    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1071   -0.0310   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7290   -0.4885   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -1.9044   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6394   -2.1230    1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -0.8074    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388   -0.8297   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    0.4918   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941    0.8924    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.0373    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845   -0.2431    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    1.0824   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970    0.9311   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3398    0.0084   -1.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.2247    0.0575   -2.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5408    0.2258   -0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6279    1.6570   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1207   -0.1915    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6583   -3.7345    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -2.0565    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6571   -0.5867    2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    0.0610    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2825   -0.9304   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -1.7028   -0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880    0.4571   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.2606   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.0324    1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153    1.8970    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.0420    1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    0.3644    2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0478   -0.7106   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032   -0.8820    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6940    1.5783    0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    1.7884   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    0.6807   -2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    1.9502   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0168   -1.0165   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6037    1.4945   -0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8848   -0.2381    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4261    0.5904    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9104    0.7631   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301   -0.3794   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7780    3.4698    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  2  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  6
 26 62  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -8.574   0.230   0.943  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.404  -0.240   0.573  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.672  -1.344   1.175  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.051  -2.067   2.143  0.00  0.00           O+0
HETATM    5  O   UNK     0      -5.448  -1.467   0.480  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.153  -0.178   0.010  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.107  -0.031  -1.004  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.729  -0.489  -0.544  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.736  -1.904  -0.187  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.472  -2.606   0.108  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.639  -2.123   1.210  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.019  -0.807   1.085  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.939  -0.830  -0.130  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.645   0.492  -0.304  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.494   0.892   0.835  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.603  -0.037   1.181  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.585  -0.243   0.050  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.206   1.082  -0.330  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.197   0.931  -1.452  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.340   0.008  -1.120  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.124   0.507   0.079  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.225   0.058  -2.211  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.541   0.226  -0.537  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.628   1.657  -0.787  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.005   2.083  -1.900  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.297   2.565   0.197  0.00  0.00           O+0
HETATM   27  H   UNK     0      -9.057   1.059   0.442  0.00  0.00           H+0
HETATM   28  H   UNK     0      -9.121  -0.192   1.776  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.973   0.536   0.862  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.038   1.053  -1.274  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.340  -0.579  -1.951  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.939  -0.134  -1.224  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.591   0.176   0.393  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.314  -2.544  -0.912  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.417  -1.979   0.750  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.836  -2.585  -0.856  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.658  -3.735   0.190  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.268  -2.057   2.172  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.117  -2.920   1.507  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.657  -0.587   2.010  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.615   0.061   1.010  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.283  -0.930  -1.014  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.617  -1.703  -0.136  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.188   0.457  -1.252  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.844   1.261  -0.425  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.871   1.032   1.765  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.915   1.897   0.636  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.268  -1.042   1.501  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.198   0.364   2.034  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.048  -0.711  -0.773  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.403  -0.882   0.462  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.694   1.578   0.521  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.425   1.788  -0.714  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.729   0.681  -2.422  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.656   1.950  -1.603  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.017  -1.016  -0.889  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.604   1.494  -0.145  0.00  0.00           H+0
HETATM   58  H   UNK     0       8.885  -0.238   0.383  0.00  0.00           H+0
HETATM   59  H   UNK     0       7.426   0.590   0.949  0.00  0.00           H+0
HETATM   60  H   UNK     0       8.910   0.763  -2.100  0.00  0.00           H+0
HETATM   61  H   UNK     0      -6.730  -0.379  -1.439  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.778   3.470   0.208  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   23   29                                             
CONECT    7    6    8   30   31                                             
CONECT    8    7    9   32   33                                             
CONECT    9    8   10   34   35                                             
CONECT   10    9   11   36   37                                             
CONECT   11   10   12   38   39                                             
CONECT   12   11   13   40   41                                             
CONECT   13   12   14   42   43                                             
CONECT   14   13   15   44   45                                             
CONECT   15   14   16   46   47                                             
CONECT   16   15   17   48   49                                             
CONECT   17   16   18   50   51                                             
CONECT   18   17   19   52   53                                             
CONECT   19   18   20   54   55                                             
CONECT   20   19   21   22   56                                             
CONECT   21   20   57   58   59                                             
CONECT   22   20   60                                                       
CONECT   23    6   24    2   61                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   62                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   22                                                            
CONECT   61   23                                                            
CONECT   62   26                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  124    0
END

RDKit          3D

62 62  0  0  0  0  0  0  0  0999 V2000
   -8.5744    0.2304    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4042   -0.2396    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6720   -1.3436    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0507   -2.0669    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4482   -1.4667    0.4802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1526   -0.1781    0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1071   -0.0310   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7290   -0.4885   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -1.9044   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725   -2.6058    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -2.1230    1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -0.8074    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388   -0.8297   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    0.4918   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941    0.8924    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.0373    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845   -0.2431    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    1.0824   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970    0.9311   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3398    0.0084   -1.1197 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1242    0.5071    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    0.0575   -2.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5408    0.2258   -0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6279    1.6570   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0051    2.0831   -1.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2971    2.5649    0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0568    1.0587    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1207   -0.1915    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735    0.5355    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382    1.0526   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396   -0.5793   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388   -0.1338   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    0.1757    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -2.5441   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166   -1.9793    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358   -2.5854   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -3.7345    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -2.0565    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169   -2.9203    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571   -0.5867    2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    0.0610    1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2825   -0.9304   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -1.7028   -0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880    0.4571   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.2606   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.0324    1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153    1.8970    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.0420    1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    0.3644    2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0478   -0.7106   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032   -0.8820    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6940    1.5783    0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    1.7884   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    0.6807   -2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    1.9502   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0168   -1.0165   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6037    1.4945   -0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8848   -0.2381    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4261    0.5904    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9104    0.7631   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301   -0.3794   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7780    3.4698    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  2  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  6
 26 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S,3R)-2-[(14S)-14-Hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylate	Generator
Protoconstipatate	Generator

Chemical Formula

C₂₁H₃₆O₅

Average Mass

368.5140 Da

Monoisotopic Mass

368.25627 Da

IUPAC Name

(2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid

Traditional Name

(2S,3R)-2-[(14S)-14-hydroxypentadecyl]-4-methylidene-5-oxooxolane-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)C(=C)[C@H]1C(O)=O

InChI Identifier

InChI=1S/C21H36O5/c1-16(22)14-12-10-8-6-4-3-5-7-9-11-13-15-18-19(20(23)24)17(2)21(25)26-18/h16,18-19,22H,2-15H2,1H3,(H,23,24)/t16-,18-,19+/m0/s1

InChI Key

UYUDMGMNHAKPEV-YTQUADARSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lecanora fructulosa	-	KNApSAcK
Lecanora frustulosa	LOTUS Database	35616633
Unknown-fungus sp.	NPAtlas	10963458

Species Where Detected

Species Name	Source	Reference
Cladonia furcata	KNApSAcK Database	22123792
Xanthoparmelia camtschadalis	KNApSAcK Database	22123792
Xanthoparmelia tinctina	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.64	ALOGPS
logP	5.47	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	101.27 m³·mol⁻¹	ChemAxon
Polarizability	43.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001997

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

168752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

194489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Protoconstipatic acid (NP0003392)

MOL for NP0003392 (Protoconstipatic acid)

3D MOL for NP0003392 (Protoconstipatic acid)

3D SDF for NP0003392 (Protoconstipatic acid)

3D-SDF for NP0003392 (Protoconstipatic acid)

PDB for NP0003392 (Protoconstipatic acid)

3D PDB for NP0003392 (Protoconstipatic acid)

SMILES for NP0003392 (Protoconstipatic acid)

INCHI for NP0003392 (Protoconstipatic acid)

Structure for NP0003392 (Protoconstipatic acid)

3D Structure for NP0003392 (Protoconstipatic acid)