NP-MRD: Showing NP-Card for Trachyspic acid (NP0022492)

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Record Information

Version

2.0

Created at

2021-01-06 07:40:19 UTC

Updated at

2021-08-20 00:00:03 UTC

NP-MRD ID

NP0022492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trachyspic acid

Provided By

NPAtlas

Description

Trachyspic acid is also known as trachyspate. Trachyspic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Trachyspic acid is found in Talaromyces and Talaromyces trachyspermus. Trachyspic acid was first documented in 1995 (PMID: 7797435). Based on a literature review a small amount of articles have been published on Trachyspic acid (PMID: 12633090) (PMID: 15917891) (PMID: 17700851) (PMID: 21879704).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105353D          

 57 58  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242105353D          

 57 58  0  0  0  0            999 V2000
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    7.5528   -0.6875    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9209   -0.0487    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3721    0.1923   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -1.4577   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2665   -1.2124   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385   -1.4963    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.9175    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.3214   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481   -0.2195   -1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    1.1162   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3827   -0.5712    1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262   -1.8442    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.9712    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.6457   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    0.8414    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    0.3645    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396   -2.3987    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708    1.2499   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -0.4632   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967   -1.3314   -1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1228   -0.4896   -2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8129    0.5832    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003    0.2314   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4710    3.6012   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4586   -2.5957   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  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  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 10  1  0  0  0  0
 27 13  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  7 43  1  0  0  0  0
  7 44  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
 11 49  1  0  0  0  0
 14 50  1  0  0  0  0
 14 51  1  0  0  0  0
 15 52  1  6  0  0  0
 18 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 23 56  1  0  0  0  0
 26 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1(O[C@@]2(OC([H])=C(C2=O)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])[H])C([H])([H])[C@]1([H])C(=O)O[H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O9/c1-2-3-4-5-6-7-8-9-13-12-28-20(16(13)23)10-14(17(24)25)19(29-20,18(26)27)11-15(21)22/h12,14H,2-11H2,1H3,(H,21,22)(H,24,25)(H,26,27)/t14-,19+,20+/m1/s1

> <INCHI_KEY>
LQLCHKHILFZNKF-UHFFFAOYSA-N

> <FORMULA>
C20H28O9

> <MOLECULAR_WEIGHT>
412.435

> <EXACT_MASS>
412.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.71032436781304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
3.8926460789999995

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.754293501568643

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6326336793207616

> <JCHEM_PKA_STRONGEST_BASIC>
-4.378125147622072

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
98.53219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    7.4096    1.4325    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970    0.0468    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1226   -0.4827   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6729   -0.7105   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    0.4839   -0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3550    0.1474   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -0.8825    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405   -1.2083    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7511    0.0204    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.2916    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242   -1.4859    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -1.4270    0.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9926   -0.0859    0.6182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2050    0.1644   -0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594   -0.2203   -1.0083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3388    0.5446   -2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    1.3462   -2.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977    0.3997   -2.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -0.1693    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4324    0.6434    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3076    2.0758    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2101    2.5633   -0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4463    2.9147    0.2022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5549   -1.5614    0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -2.0335    1.8022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5386   -2.3022    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686    0.2705    1.2062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    0.6230    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654    1.7475    1.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3930    1.9938    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9514    1.9499    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8614    1.5076    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5528   -0.6875    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9209   -0.0487    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3721    0.1923   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -1.4577   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2665   -1.2124   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385   -1.4963    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.9175    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.3214   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481   -0.2195   -1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    1.1162   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3827   -0.5712    1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262   -1.8442    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.9712    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.6457   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    0.8414    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    0.3645    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396   -2.3987    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708    1.2499   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -0.4632   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967   -1.3314   -1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1228   -0.4896   -2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8129    0.5832    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003    0.2314   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4710    3.6012   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4586   -2.5957   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 13 12  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  1
 24 25  2  0
 24 26  1  0
 19 27  1  0
 13 28  1  0
 28 29  2  0
 28 10  1  0
 27 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 11 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 18 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 26 57  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       7.410   1.433   0.848  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.797   0.047   0.443  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.123  -0.483  -0.753  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.673  -0.711  -0.656  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.854   0.484  -0.383  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.355   0.147  -0.407  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.043  -0.883   0.642  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.541  -1.208   0.634  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.751   0.020   0.923  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.702  -0.292   0.923  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.224  -1.486   0.700  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.607  -1.427   0.773  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.993  -0.086   0.618  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.205   0.164  -0.844  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.659  -0.220  -1.008  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.339   0.545  -2.045  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.717   1.346  -2.779  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.698   0.400  -2.247  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.193  -0.169   0.368  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.432   0.643   0.536  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.308   2.076   0.208  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.210   2.563  -0.067  0.00  0.00           O+0
HETATM   23  O   UNK     0      -7.446   2.915   0.202  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.555  -1.561   0.826  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.938  -2.034   1.802  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.539  -2.302   0.193  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.169   0.271   1.206  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.814   0.623   1.158  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.765   1.748   1.695  0.00  0.00           O+0
HETATM   30  H   UNK     0       8.393   1.994   1.094  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.951   1.950   0.004  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.861   1.508   1.785  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.553  -0.688   1.293  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.921  -0.049   0.378  0.00  0.00           H+0
HETATM   35  H   UNK     0       7.372   0.192  -1.632  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.673  -1.458  -1.034  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.266  -1.212  -1.582  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.439  -1.496   0.144  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.022   0.918   0.649  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.960   1.321  -1.090  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.148  -0.220  -1.427  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.861   1.116  -0.176  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.383  -0.571   1.634  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.526  -1.844   0.312  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.370  -1.971   1.413  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.345  -1.646  -0.358  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.919   0.841   0.228  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.016   0.365   1.950  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.640  -2.399   0.486  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.071   1.250  -1.080  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.541  -0.463  -1.484  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.597  -1.331  -1.326  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.123  -0.490  -2.518  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.813   0.583   1.609  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.300   0.231  -0.040  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.471   3.601  -0.537  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.459  -2.596  -0.782  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   33   34                                             
CONECT    3    2    4   35   36                                             
CONECT    4    3    5   37   38                                             
CONECT    5    4    6   39   40                                             
CONECT    6    5    7   41   42                                             
CONECT    7    6    8   43   44                                             
CONECT    8    7    9   45   46                                             
CONECT    9    8   10   47   48                                             
CONECT   10    9   11   28                                                  
CONECT   11   10   12   49                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28   27                                             
CONECT   14   13   15   50   51                                             
CONECT   15   14   16   19   52                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   53                                                       
CONECT   19   15   20   24   27                                             
CONECT   20   19   21   54   55                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   56                                                       
CONECT   24   19   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   57                                                       
CONECT   27   19   13                                                       
CONECT   28   13   29   10                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   11                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   23                                                            
CONECT   57   26                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  116    0
END

RDKit          3D

57 58  0  0  0  0  0  0  0  0999 V2000
    7.4096    1.4325    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970    0.0468    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1226   -0.4827   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6729   -0.7105   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    0.4839   -0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3550    0.1474   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -0.8825    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405   -1.2083    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7511    0.0204    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.2916    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242   -1.4859    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -1.4270    0.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9926   -0.0859    0.6182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2050    0.1644   -0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594   -0.2203   -1.0083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3388    0.5446   -2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    1.3462   -2.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977    0.3997   -2.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -0.1693    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4324    0.6434    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3076    2.0758    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2101    2.5633   -0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4463    2.9147    0.2022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5549   -1.5614    0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -2.0335    1.8022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5386   -2.3022    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686    0.2705    1.2062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    0.6230    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654    1.7475    1.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3930    1.9938    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9514    1.9499    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8614    1.5076    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5528   -0.6875    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9209   -0.0487    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3721    0.1923   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -1.4577   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2665   -1.2124   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385   -1.4963    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    0.9175    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.3214   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481   -0.2195   -1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    1.1162   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3827   -0.5712    1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262   -1.8442    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.9712    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.6457   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    0.8414    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    0.3645    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396   -2.3987    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708    1.2499   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -0.4632   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967   -1.3314   -1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1228   -0.4896   -2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8129    0.5832    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003    0.2314   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4710    3.6012   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4586   -2.5957   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 13 12  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  1
 24 25  2  0
 24 26  1  0
 19 27  1  0
 13 28  1  0
 28 29  2  0
 28 10  1  0
 27 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 11 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 18 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 26 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Trachyspate	Generator

Chemical Formula

C₂₀H₂₈O₉

Average Mass

412.4350 Da

Monoisotopic Mass

412.17333 Da

IUPAC Name

(2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid

Traditional Name

(2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC1=COC2(CC(C(O)=O)C(CC(O)=O)(O2)C(O)=O)C1=O

InChI Identifier

InChI=1S/C20H28O9/c1-2-3-4-5-6-7-8-9-13-12-28-20(16(13)23)10-14(17(24)25)19(29-20,18(26)27)11-15(21)22/h12,14H,2-11H2,1H3,(H,21,22)(H,24,25)(H,26,27)

InChI Key

LQLCHKHILFZNKF-UHFFFAOYSA-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
Talaromyces	NPAtlas	7797435
Talaromyces trachyspermus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Talaromyces trachyspermus SANK 12191	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Ketal
3-furanone
Dihydrofuran
Oxolane
Vinylogous ester
Ketone
Acetal
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.15 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.41	ALOGPS
logP	3.89	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.53 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001236

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016490

Chemspider ID

8085239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trachyspic_acid

METLIN ID

Not Available

PubChem Compound

9909587

PDB ID

Not Available

ChEBI ID

66260

Good Scents ID

rw1488131

References

General References

Shiozawa H, Takahashi M, Takatsu T, Kinoshita T, Tanzawa K, Hosoya T, Furuya K, Takahashi S, Furihata K, Seto H: Trachyspic acid, a new metabolite produced by Talaromyces trachyspermus, that inhibits tumor cell heparanase: taxonomy of the producing strain, fermentation, isolation, structural elucidation, and biological activity. J Antibiot (Tokyo). 1995 May;48(5):357-62. doi: 10.7164/antibiotics.48.357. [PubMed:7797435 ]
Hirai K, Ooi H, Esumi T, Iwabuchi Y, Hatakeyama S: Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration. Org Lett. 2003 Mar 20;5(6):857-9. doi: 10.1021/ol0275264. [PubMed:12633090 ]
Zammit SC, White JM, Rizzacasa MA: Enantiospecific synthesis of (-)-trachyspic acid. Org Biomol Chem. 2005 Jun 7;3(11):2073-4. doi: 10.1039/b504258e. Epub 2005 May 6. [PubMed:15917891 ]
Zammit SC, Ferro V, Hammond E, Rizzacasa MA: Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor. Org Biomol Chem. 2007 Sep 7;5(17):2826-34. doi: 10.1039/b708594j. Epub 2007 Jul 26. [PubMed:17700851 ]
Schmitt DC, Lam L, Johnson JS: Three-component coupling approach to trachyspic acid. Org Lett. 2011 Oct 7;13(19):5136-9. doi: 10.1021/ol202002r. Epub 2011 Aug 31. [PubMed:21879704 ]

Showing NP-Card for Trachyspic acid (NP0022492)

MOL for NP0022492 (Trachyspic acid)

3D MOL for NP0022492 (Trachyspic acid)

3D SDF for NP0022492 (Trachyspic acid)

3D-SDF for NP0022492 (Trachyspic acid)

PDB for NP0022492 (Trachyspic acid)

3D PDB for NP0022492 (Trachyspic acid)

SMILES for NP0022492 (Trachyspic acid)

INCHI for NP0022492 (Trachyspic acid)

Structure for NP0022492 (Trachyspic acid)

3D Structure for NP0022492 (Trachyspic acid)