NP-MRD: Showing NP-Card for fuligoic acid (NP0038350)

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Record Information

Version

2.0

Created at

2021-06-20 21:03:52 UTC

Updated at

2021-06-30 00:11:05 UTC

NP-MRD ID

NP0038350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fuligoic acid

Provided By

JEOL Database JEOL Logo

Description

(2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]nona-2,4,6,8-tetraenoic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. fuligoic acid is found in Fuligo septica and Fuligo septica f. flava. fuligoic acid was first documented in 2009 (Shintani, A., et al.). Based on a literature review very few articles have been published on (2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]nona-2,4,6,8-tetraenoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123033D          

 36 36  0  0  0  0            999 V2000
    6.7117   -5.1312    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -4.5431    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -4.6022    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -5.1366    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -5.1867    3.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -5.8637    4.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -4.4876    2.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -3.4499    1.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9773   -2.9941    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651   -1.7182    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -1.3119    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0359    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.3707   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    1.6476   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    2.0516   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    3.3020   -1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    4.6848   -0.8265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5342    3.4950   -2.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    2.6179   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    4.7750   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -3.9714    0.7513 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9008   -4.6297    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -6.2050    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5952   -5.0001    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -5.6153    3.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -2.6254    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -3.7749    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -0.9405    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -2.0936   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    0.7453    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -0.4135   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    2.4209   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.2404   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    4.7411   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -4.7280    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -3.1450    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  8 21  1  0  0  0  0
 13 14  2  0  0  0  0
 21  3  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8  9  1  0  0  0  0
 16 18  1  0  0  0  0
  4  5  1  0  0  0  0
 18 20  1  0  0  0  0
  9 10  2  0  0  0  0
 18 19  2  0  0  0  0
  4  3  2  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  3  2  1  0  0  0  0
 11 12  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8 26  1  1  0  0  0
  4 25  1  0  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 20 34  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    6.7117   -5.1312    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -4.5431    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -4.6022    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -5.1366    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -5.1867    3.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -5.8637    4.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -4.4876    2.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -3.4499    1.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9773   -2.9941    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651   -1.7182    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -1.3119    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0359    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.3707   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    1.6476   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    2.0516   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    3.3020   -1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    4.6848   -0.8265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5342    3.4950   -2.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    2.6179   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    4.7750   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -3.9714    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9008   -4.6297    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -6.2050    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5952   -5.0001    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -5.6153    3.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -2.6254    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -3.7749    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -0.9405    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -2.0936   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    0.7453    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -0.4135   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    2.4209   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.2404   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    4.7411   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -4.7280    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -3.1450    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  8 21  1  0
 13 14  2  0
 21  3  1  0
 14 15  1  0
 15 16  2  0
  8  9  1  0
 16 18  1  0
  4  5  1  0
 18 20  1  0
  9 10  2  0
 18 19  2  0
  4  3  2  0
 16 17  1  0
 10 11  1  0
  5  6  2  0
  5  7  1  0
  3  2  1  0
 11 12  2  0
  2  1  1  0
  7  8  1  0
  8 26  1  1
  4 25  1  0
 21 35  1  0
 21 36  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 20 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306202123033D          

 36 36  0  0  0  0            999 V2000
    6.7117   -5.1312    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -4.5431    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -4.6022    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -5.1366    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -5.1867    3.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -5.8637    4.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -4.4876    2.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -3.4499    1.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9773   -2.9941    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651   -1.7182    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -1.3119    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0359    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.3707   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    1.6476   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    2.0516   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    3.3020   -1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    4.6848   -0.8265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5342    3.4950   -2.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    2.6179   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    4.7750   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -3.9714    0.7513 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9008   -4.6297    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -6.2050    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5952   -5.0001    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -5.6153    3.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -2.6254    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -3.7749    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -0.9405    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -2.0936   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    0.7453    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -0.4135   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    2.4209   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.2404   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    4.7411   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -4.7280    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -3.1450    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  8 21  1  0  0  0  0
 13 14  2  0  0  0  0
 21  3  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8  9  1  0  0  0  0
 16 18  1  0  0  0  0
  4  5  1  0  0  0  0
 18 20  1  0  0  0  0
  9 10  2  0  0  0  0
 18 19  2  0  0  0  0
  4  3  2  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  3  2  1  0  0  0  0
 11 12  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8 26  1  1  0  0  0
  4 25  1  0  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 20 34  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\Cl)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])[C@@]1([H])OC(=O)C([H])=C(OC([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H15ClO5/c1-20-12-9-11(21-14(17)10-12)7-5-3-2-4-6-8-13(16)15(18)19/h2-8,10-11H,9H2,1H3,(H,18,19)/b3-2+,6-4+,7-5+,13-8-/t11-/m1/s1

> <INCHI_KEY>
MNZFRTMXWSABEV-FXCHFOLMSA-N

> <FORMULA>
C15H15ClO5

> <MOLECULAR_WEIGHT>
310.73

> <EXACT_MASS>
310.0608013

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.444277264019192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
2.2263104239999993

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.598384279268032

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.924682034953773

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788416679286767

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
84.65189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]nona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    6.7117   -5.1312    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -4.5431    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -4.6022    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -5.1366    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -5.1867    3.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -5.8637    4.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -4.4876    2.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -3.4499    1.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9773   -2.9941    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651   -1.7182    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -1.3119    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0359    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.3707   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    1.6476   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    2.0516   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    3.3020   -1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    4.6848   -0.8265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5342    3.4950   -2.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    2.6179   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    4.7750   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -3.9714    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9008   -4.6297    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -6.2050    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5952   -5.0001    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -5.6153    3.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -2.6254    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -3.7749    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -0.9405    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -2.0936   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    0.7453    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -0.4135   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    2.4209   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.2404   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    4.7411   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -4.7280    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -3.1450    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  8 21  1  0
 13 14  2  0
 21  3  1  0
 14 15  1  0
 15 16  2  0
  8  9  1  0
 16 18  1  0
  4  5  1  0
 18 20  1  0
  9 10  2  0
 18 19  2  0
  4  3  2  0
 16 17  1  0
 10 11  1  0
  5  6  2  0
  5  7  1  0
  3  2  1  0
 11 12  2  0
  2  1  1  0
  7  8  1  0
  8 26  1  1
  4 25  1  0
 21 35  1  0
 21 36  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 20 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       6.712  -5.131   1.610  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.602  -4.543   0.938  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.372  -4.602   1.553  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.098  -5.137   2.754  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.721  -5.187   3.278  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.463  -5.864   4.265  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.775  -4.488   2.607  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.200  -3.450   1.706  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.977  -2.994   0.956  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.565  -1.718   0.895  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.619  -1.312   0.171  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.027  -0.036   0.102  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.213   0.371  -0.621  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.621   1.648  -0.690  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.811   2.052  -1.416  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.292   3.302  -1.539  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -3.540   4.685  -0.827  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -5.534   3.495  -2.332  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.170   2.618  -2.895  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.944   4.775  -2.398  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.271  -3.971   0.751  0.00  0.00           C+0
HETATM   22  H   UNK     0       6.901  -4.630   2.564  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.556  -6.205   1.755  0.00  0.00           H+0
HETATM   24  H   UNK     0       7.595  -5.000   0.978  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.836  -5.615   3.383  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.595  -2.625   2.315  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.410  -3.775   0.453  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.129  -0.941   1.406  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.187  -2.094  -0.330  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.460   0.745   0.605  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.780  -0.414  -1.119  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.045   2.421  -0.186  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.355   1.240  -1.902  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.757   4.741  -2.942  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.865  -4.728   0.067  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.659  -3.145   0.144  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3   21    4    2                                                  
CONECT    4    5    3   25                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8   21    9    7   26                                             
CONECT    9    8   10   27                                                  
CONECT   10    9   11   28                                                  
CONECT   11   10   12   29                                                  
CONECT   12   13   11   30                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   20   19                                                  
CONECT   19   18                                                            
CONECT   20   18   34                                                       
CONECT   21    8    3   35   36                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   21                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

RDKit          3D

36 36  0  0  0  0  0  0  0  0999 V2000
    6.7117   -5.1312    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -4.5431    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -4.6022    1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -5.1366    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -5.1867    3.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -5.8637    4.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -4.4876    2.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -3.4499    1.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9773   -2.9941    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651   -1.7182    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -1.3119    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.0359    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.3707   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    1.6476   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    2.0516   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919    3.3020   -1.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    4.6848   -0.8265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5342    3.4950   -2.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    2.6179   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9437    4.7750   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -3.9714    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9008   -4.6297    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -6.2050    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5952   -5.0001    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -5.6153    3.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -2.6254    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -3.7749    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -0.9405    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -2.0936   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    0.7453    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -0.4135   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    2.4209   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.2404   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    4.7411   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -4.7280    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6591   -3.1450    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  8 21  1  0
 13 14  2  0
 21  3  1  0
 14 15  1  0
 15 16  2  0
  8  9  1  0
 16 18  1  0
  4  5  1  0
 18 20  1  0
  9 10  2  0
 18 19  2  0
  4  3  2  0
 16 17  1  0
 10 11  1  0
  5  6  2  0
  5  7  1  0
  3  2  1  0
 11 12  2  0
  2  1  1  0
  7  8  1  0
  8 26  1  1
  4 25  1  0
 21 35  1  0
 21 36  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 20 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2Z,4E,6E,8E)-2-Chloro-9-[(2S)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]nona-2,4,6,8-tetraenoate	Generator
Fuligoate	Generator

Chemical Formula

C₁₅H₁₅ClO₅

Average Mass

310.7300 Da

Monoisotopic Mass

310.06080 Da

IUPAC Name

(2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]nona-2,4,6,8-tetraenoic acid

Traditional Name

(2Z,4E,6E,8E)-2-chloro-9-[(2S)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]nona-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\Cl)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])[C@@]1([H])OC(=O)C([H])=C(OC([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C15H15ClO5/c1-20-12-9-11(21-14(17)10-12)7-5-3-2-4-6-8-13(16)15(18)19/h2-8,10-11H,9H2,1H3,(H,18,19)/b3-2+,6-4+,7-5+,13-8-/t11-/m1/s1

InChI Key

MNZFRTMXWSABEV-FXCHFOLMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fuligo septica	LOTUS Database	35616633
Fuligo septica var. flava	JEOL database	Shintani, A., et al, Tetrahedron Lett. 50, 3189 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Dihydropyranone
Halogenated fatty acid
Heterocyclic fatty acid
Dicarboxylic acid or derivatives
Pyran
Unsaturated fatty acid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Alpha-halocarboxylic acid
Alpha-halocarboxylic acid or derivatives
Carboxylic acid ester
Lactone
Oxacycle
Haloalkene
Carboxylic acid
Chloroalkene
Carboxylic acid derivative
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.52	ALOGPS
logP	2.23	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.65 m³·mol⁻¹	ChemAxon
Polarizability	31.44 Å³	ChemAxon
Number of Rings	1	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101782956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shintani, A., et al. (2009). Shintani, A., et al, Tetrahedron Lett. 50, 3189 (2009). Tetrahedron Lett.

Showing NP-Card for fuligoic acid (NP0038350)

MOL for NP0038350 (fuligoic acid)

3D MOL for NP0038350 (fuligoic acid)

3D SDF for NP0038350 (fuligoic acid)

3D-SDF for NP0038350 (fuligoic acid)

PDB for NP0038350 (fuligoic acid)

3D PDB for NP0038350 (fuligoic acid)

SMILES for NP0038350 (fuligoic acid)

INCHI for NP0038350 (fuligoic acid)

Structure for NP0038350 (fuligoic acid)

3D Structure for NP0038350 (fuligoic acid)