NP-MRD: Showing NP-Card for Sydonic acid (NP0008189)

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Record Information

Version

2.0

Created at

2020-12-09 05:50:46 UTC

Updated at

2021-07-15 16:59:41 UTC

NP-MRD ID

NP0008189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sydonic acid

Provided By

NPAtlas

Description

(+)-(7S)-sydonic 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. Sydonic acid is found in Glonium sp. Sydonic acid was first documented in 2009 (PMID: 19129640). Based on a literature review very few articles have been published on (+)-(7S)-sydonic acid (PMID: 20415462) (PMID: 21718031).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106073D          

 41 41  0  0  0  0            999 V2000
    4.5846    0.3983   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    0.1764    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1134    1.0728    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5081    0.5609 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8217   -0.3247   -0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4276    0.1009    0.1663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6160   -0.6827   -0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3992   -2.1442   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -0.5503   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.2930   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869    0.7626    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.1074    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    0.4232    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9051    0.8237    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956    0.2193    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497    1.8738    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -0.6319   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.0007   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0603   -1.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -0.4649   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4208   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.3555   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8636    0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    2.0983    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.7666    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.0753    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.3047    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.5909    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450   -1.3900   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.1507   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -0.0770    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1886    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -2.6512   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -2.2556    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442   -2.6693   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232    0.3200   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3241    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475    1.9461    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7206    2.0262    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.1238   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.5497   -2.0908 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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  1  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 19 41  1  0  0  0  0
M  END

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    4.5846    0.3983   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    0.1764    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1134    1.0728    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5081    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217   -0.3247   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    0.1009    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.6827   -0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3992   -2.1442   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -0.5503   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.2930   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869    0.7626    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.1074    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    0.4232    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9051    0.8237    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956    0.2193    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497    1.8738    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -0.6319   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.0007   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0603   -1.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -0.4649   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4208   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.3555   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8636    0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    2.0983    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.7666    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.0753    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.3047    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.5909    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450   -1.3900   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.1507   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -0.0770    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1886    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -2.6512   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -2.2556    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442   -2.6693   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232    0.3200   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3241    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475    1.9461    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7206    2.0262    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.1238   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.5497   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 18 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
M  END


  Mrv1652306242106073D          

 41 41  0  0  0  0            999 V2000
    4.5846    0.3983   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    0.1764    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1134    1.0728    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5081    0.5609 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8217   -0.3247   -0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4276    0.1009    0.1663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6160   -0.6827   -0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3992   -2.1442   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -0.5503   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.2930   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869    0.7626    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.1074    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    0.4232    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9051    0.8237    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956    0.2193    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497    1.8738    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -0.6319   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.0007   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0603   -1.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -0.4649   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4208   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.3555   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8636    0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    2.0983    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.7666    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.0753    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.3047    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.5909    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450   -1.3900   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.1507   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -0.0770    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1886    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -2.6512   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -2.2556    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442   -2.6693   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232    0.3200   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3241    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475    1.9461    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7206    2.0262    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.1238   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.5497   -2.0908 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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  1  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 19 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(C(O[H])=C1[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-10(2)5-4-8-15(3,19)12-7-6-11(14(17)18)9-13(12)16/h6-7,9-10,16,19H,4-5,8H2,1-3H3,(H,17,18)/t15-/m0/s1

> <INCHI_KEY>
VZXPWVDKXCYHSI-HNNXBMFYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.042949306019512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4-[(2S)-2-hydroxy-6-methylheptan-2-yl]benzoic acid

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.4003128143333337

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.878914105358577

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8308136522094256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2374050188943855

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
74.0436

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-[(2S)-2-hydroxy-6-methylheptan-2-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    4.5846    0.3983   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    0.1764    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1134    1.0728    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5081    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217   -0.3247   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    0.1009    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.6827   -0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3992   -2.1442   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -0.5503   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.2930   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869    0.7626    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.1074    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    0.4232    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9051    0.8237    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956    0.2193    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497    1.8738    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -0.6319   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.0007   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0603   -1.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -0.4649   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4208   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.3555   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8636    0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    2.0983    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.7666    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.0753    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.3047    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.5909    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450   -1.3900   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.1507   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -0.0770    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1886    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -2.6512   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -2.2556    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442   -2.6693   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232    0.3200   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3241    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475    1.9461    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7206    2.0262    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.1238   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.5497   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
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 13 17  1  0
 17 18  2  0
 18 19  1  0
 18 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
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  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  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       4.585   0.398  -1.189  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.229   0.176   0.244  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.113   1.073   1.087  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.793   0.508   0.561  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.822  -0.325  -0.241  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.428   0.101   0.166  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.616  -0.683  -0.588  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.399  -2.144  -0.251  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.460  -0.550  -1.972  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.988  -0.293  -0.258  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.187   0.763   0.608  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.490   1.107   0.903  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.547   0.423   0.352  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.905   0.824   0.693  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.896   0.219   0.207  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.150   1.874   1.555  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.309  -0.632  -0.514  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.019  -1.001  -0.828  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.829  -2.060  -1.697  0.00  0.00           O+0
HETATM   20  H   UNK     0       4.281  -0.465  -1.848  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.708   0.421  -1.254  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.244   1.355  -1.602  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.493  -0.864   0.508  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.729   2.098   1.043  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.047   0.767   2.169  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.170   1.075   0.734  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.622   0.305   1.637  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.627   1.591   0.395  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.945  -1.390  -0.022  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.913  -0.151  -1.323  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.279  -0.077   1.250  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.371   1.189   0.001  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.159  -2.651  -1.050  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.237  -2.256   0.676  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.344  -2.669  -0.001  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.123   0.320  -2.242  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.361   1.324   1.061  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.648   1.946   1.591  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.721   2.026   2.438  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.189  -1.124  -0.909  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.612  -2.550  -2.091  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    4   23                                             
CONECT    3    2   24   25   26                                             
CONECT    4    2    5   27   28                                             
CONECT    5    4    6   29   30                                             
CONECT    6    5    7   31   32                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7   33   34   35                                             
CONECT    9    7   36                                                       
CONECT   10    7   11   18                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13   38                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   39                                                       
CONECT   17   13   18   40                                                  
CONECT   18   17   19   10                                                  
CONECT   19   18   41                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   19                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   82    0
END

RDKit          3D

41 41  0  0  0  0  0  0  0  0999 V2000
    4.5846    0.3983   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    0.1764    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1134    1.0728    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    0.5081    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217   -0.3247   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    0.1009    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.6827   -0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3992   -2.1442   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -0.5503   -1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.2930   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869    0.7626    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.1074    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    0.4232    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9051    0.8237    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8956    0.2193    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497    1.8738    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -0.6319   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.0007   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -2.0603   -1.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -0.4649   -1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.4208   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.3555   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -0.8636    0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    2.0983    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474    0.7666    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.0753    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.3047    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    1.5909    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450   -1.3900   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.1507   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -0.0770    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.1886    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -2.6512   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -2.2556    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442   -2.6693   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232    0.3200   -2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3241    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475    1.9461    1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7206    2.0262    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.1238   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.5497   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 18 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(+)-(7S)-Sydonate	Generator
Sydonate	Generator

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

3-hydroxy-4-[(2S)-2-hydroxy-6-methylheptan-2-yl]benzoic acid

Traditional Name

3-hydroxy-4-[(2S)-2-hydroxy-6-methylheptan-2-yl]benzoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@](C)(O)C1=C(O)C=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C15H22O4/c1-10(2)5-4-8-15(3,19)12-7-6-11(14(17)18)9-13(12)16/h6-7,9-10,16,19H,4-5,8H2,1-3H3,(H,17,18)/t15-/m0/s1

InChI Key

VZXPWVDKXCYHSI-HNNXBMFYSA-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
Glonium sp.	NPAtlas	19129640

Species Where Detected

Species Name	Source	Reference
Aspergillus sydowii	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	3.27	ALOGPS
logP	3.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.04 m³·mol⁻¹	ChemAxon
Polarizability	30.04 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

NPAtlas ID

NPA009167

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29402471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25775004

PDB ID

Not Available

ChEBI ID

68223

Good Scents ID

Not Available

References

General References

Kudo S, Murakami T, Miyanishi J, Tanaka K, Takada N, Hashimoto M: Isolation and absolute stereochemistry of optically active sydonic acid from Glonium sp. (Hysteriales, Ascomycota). Biosci Biotechnol Biochem. 2009 Jan;73(1):203-4. doi: 10.1271/bbb.80535. Epub 2009 Jan 7. [PubMed:19129640 ]
Lu Z, Zhu H, Fu P, Wang Y, Zhang Z, Lin H, Liu P, Zhuang Y, Hong K, Zhu W: Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum. J Nat Prod. 2010 May 28;73(5):911-4. doi: 10.1021/np100059m. [PubMed:20415462 ]
Trisuwan K, Rukachaisirikul V, Kaewpet M, Phongpaichit S, Hutadilok-Towatana N, Preedanon S, Sakayaroj J: Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154. J Nat Prod. 2011 Jul 22;74(7):1663-7. doi: 10.1021/np200374j. Epub 2011 Jun 30. [PubMed:21718031 ]

Showing NP-Card for Sydonic acid (NP0008189)

MOL for NP0008189 (Sydonic acid)

3D MOL for NP0008189 (Sydonic acid)

3D SDF for NP0008189 (Sydonic acid)

3D-SDF for NP0008189 (Sydonic acid)

PDB for NP0008189 (Sydonic acid)

3D PDB for NP0008189 (Sydonic acid)

SMILES for NP0008189 (Sydonic acid)

INCHI for NP0008189 (Sydonic acid)

Structure for NP0008189 (Sydonic acid)

3D Structure for NP0008189 (Sydonic acid)