NP-MRD: Showing NP-Card for phenatic acid B (NP0028163)

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Record Information

Version

2.0

Created at

2021-06-19 20:07:27 UTC

Updated at

2021-06-29 23:54:46 UTC

NP-MRD ID

NP0028163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phenatic acid B

Provided By

JEOL Database JEOL Logo

Description

(2S,3S)-Phenatic acid B is also known as (2S,3S)-phenatate b. phenatic acid B is found in Streptomyces sp. K03-0132. phenatic acid B was first documented in 2005 (Fukuda, T., et al.). Based on a literature review very few articles have been published on (2S,3S)-Phenatic acid B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122073D          

 37 38  0  0  0  0            999 V2000
   -1.0338    0.2243    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.4116    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    1.1889    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.4067   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    2.2441   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.8419   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.0934   -2.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    0.0612   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.5361   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.2054   -3.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.5398   -2.2900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8627   -1.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -0.6051   -2.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.0479   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -1.2322   -4.1590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7612   -2.2187   -3.5984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4107   -3.5956   -3.3622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3925   -4.6323   -2.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2470   -4.4261   -2.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -5.8795   -3.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -0.1382    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.0185    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    0.2467    3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -0.7447    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    1.6334    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    3.1308   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6622   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    2.5858    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.7038   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.2748   -1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4521   -4.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.7157   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.3478   -4.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795   -3.9347   -4.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -3.5477   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520   -6.4597   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.7104    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  3  2  2  0  0  0  0
 18 19  2  0  0  0  0
  8  6  1  0  0  0  0
 18 20  1  0  0  0  0
  6  4  2  0  0  0  0
  6  7  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 16 11  1  0  0  0  0
  9 11  1  0  0  0  0
  2 21  1  0  0  0  0
  9 10  2  0  0  0  0
 16 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 21  8  2  0  0  0  0
 13 14  2  0  0  0  0
  3 25  1  0  0  0  0
 21 37  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 20 36  1  0  0  0  0
  7 29  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  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
 16 33  1  0  0  0  0
 11 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.0338    0.2243    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.4116    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    1.1889    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.4067   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    2.2441   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.8419   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.0934   -2.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    0.0612   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.5361   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.2054   -3.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.5398   -2.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8627   -1.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -0.6051   -2.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.0479   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -1.2322   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -2.2187   -3.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -3.5956   -3.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925   -4.6323   -2.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2470   -4.4261   -2.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -5.8795   -3.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -0.1382    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.0185    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    0.2467    3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -0.7447    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    1.6334    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    3.1308   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6622   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    2.5858    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.7038   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.2748   -1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4521   -4.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.7157   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.3478   -4.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795   -3.9347   -4.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -3.5477   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520   -6.4597   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.7104    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  3  2  2  0
 18 19  2  0
  8  6  1  0
 18 20  1  0
  6  4  2  0
  6  7  1  0
  4  3  1  0
  4  5  1  0
  8  9  1  0
  2  1  1  0
 16 11  1  0
  9 11  1  0
  2 21  1  0
  9 10  2  0
 16 17  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 15 16  1  0
 21  8  2  0
 13 14  2  0
  3 25  1  0
 21 37  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
  7 29  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 16 33  1  0
 11 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv1652306192122073D          

 37 38  0  0  0  0            999 V2000
   -1.0338    0.2243    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.4116    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    1.1889    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.4067   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    2.2441   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.8419   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.0934   -2.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    0.0612   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.5361   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.2054   -3.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.5398   -2.2900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8627   -1.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -0.6051   -2.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.0479   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -1.2322   -4.1590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7612   -2.2187   -3.5984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4107   -3.5956   -3.3622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3925   -4.6323   -2.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2470   -4.4261   -2.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -5.8795   -3.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -0.1382    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.0185    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    0.2467    3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -0.7447    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    1.6334    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    3.1308   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6622   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    2.5858    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.7038   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.2748   -1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4521   -4.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.7157   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.3478   -4.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795   -3.9347   -4.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -3.5477   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520   -6.4597   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.7104    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  3  2  2  0  0  0  0
 18 19  2  0  0  0  0
  8  6  1  0  0  0  0
 18 20  1  0  0  0  0
  6  4  2  0  0  0  0
  6  7  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 16 11  1  0  0  0  0
  9 11  1  0  0  0  0
  2 21  1  0  0  0  0
  9 10  2  0  0  0  0
 16 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 21  8  2  0  0  0  0
 13 14  2  0  0  0  0
  3 25  1  0  0  0  0
 21 37  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 20 36  1  0  0  0  0
  7 29  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  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
 16 33  1  0  0  0  0
 11 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])C([H])([H])C(=O)O[C@]1([H])C(=O)C1=C([H])C(=C([H])C(=C1O[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-7-3-8(2)13(19)10(4-7)14(20)15-9(5-11(16)17)6-12(18)21-15/h3-4,9,15,19H,5-6H2,1-2H3,(H,16,17)/t9-,15-/m0/s1

> <INCHI_KEY>
XMMWCOYSUBFDCF-VFZGTOFNSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.303215835542364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,3S)-2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
2.4563071339999993

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.737004501396813

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8798231814419197

> <JCHEM_PKA_STRONGEST_BASIC>
-5.153265097922966

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
72.7564

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S)-2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.0338    0.2243    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.4116    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    1.1889    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.4067   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    2.2441   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.8419   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.0934   -2.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    0.0612   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.5361   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.2054   -3.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.5398   -2.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8627   -1.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -0.6051   -2.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.0479   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -1.2322   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -2.2187   -3.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -3.5956   -3.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925   -4.6323   -2.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2470   -4.4261   -2.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -5.8795   -3.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -0.1382    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.0185    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    0.2467    3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -0.7447    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    1.6334    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    3.1308   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6622   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    2.5858    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.7038   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.2748   -1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4521   -4.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.7157   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.3478   -4.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795   -3.9347   -4.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -3.5477   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520   -6.4597   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.7104    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  3  2  2  0
 18 19  2  0
  8  6  1  0
 18 20  1  0
  6  4  2  0
  6  7  1  0
  4  3  1  0
  4  5  1  0
  8  9  1  0
  2  1  1  0
 16 11  1  0
  9 11  1  0
  2 21  1  0
  9 10  2  0
 16 17  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 15 16  1  0
 21  8  2  0
 13 14  2  0
  3 25  1  0
 21 37  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
  7 29  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 16 33  1  0
 11 30  1  0
 15 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.034   0.224   2.524  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.444   0.412   1.156  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.707   1.189   0.985  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.247   1.407  -0.289  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.484   2.244  -0.452  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.609   0.842  -1.403  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.176   1.093  -2.628  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.553   0.061  -1.256  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.206  -0.536  -2.463  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.795  -0.205  -3.579  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.354  -1.540  -2.290  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.531  -0.863  -1.850  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.337  -0.605  -2.921  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.364   0.048  -2.858  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.774  -1.232  -4.159  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.761  -2.219  -3.598  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.411  -3.596  -3.362  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.393  -4.632  -2.966  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.247  -4.426  -2.605  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.892  -5.880  -3.018  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.075  -0.138   0.031  0.00  0.00           C+0
HETATM   22  H   UNK     0      -1.758   1.018   2.731  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.254   0.247   3.293  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.538  -0.745   2.602  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.188   1.633   1.855  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.264   3.131  -1.056  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.276   1.662  -0.935  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.868   2.586   0.515  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.599   0.704  -3.321  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.058  -2.275  -1.536  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.290  -0.452  -4.755  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.561  -1.716  -4.742  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.918  -2.348  -4.287  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.880  -3.935  -4.294  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.177  -3.548  -2.581  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.152  -6.460  -2.740  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.986  -0.710   0.188  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1   21                                                  
CONECT    3    2    4   25                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4   26   27   28                                             
CONECT    6    8    4    7                                                  
CONECT    7    6   29                                                       
CONECT    8    6    9   21                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11   16    9   12   30                                             
CONECT   12   11   13                                                       
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   16   31   32                                             
CONECT   16   11   17   15   33                                             
CONECT   17   18   16   34   35                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   36                                                       
CONECT   21    2    8   37                                                  
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30   11                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
   -1.0338    0.2243    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.4116    1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    1.1889    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.4067   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    2.2441   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.8419   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.0934   -2.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    0.0612   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.5361   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.2054   -3.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.5398   -2.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8627   -1.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -0.6051   -2.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.0479   -2.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -1.2322   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -2.2187   -3.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -3.5956   -3.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925   -4.6323   -2.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2470   -4.4261   -2.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921   -5.8795   -3.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754   -0.1382    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    1.0185    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    0.2467    3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -0.7447    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    1.6334    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    3.1308   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6622   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    2.5858    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.7038   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -2.2748   -1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4521   -4.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612   -1.7157   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.3478   -4.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795   -3.9347   -4.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -3.5477   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520   -6.4597   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.7104    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  3  2  2  0
 18 19  2  0
  8  6  1  0
 18 20  1  0
  6  4  2  0
  6  7  1  0
  4  3  1  0
  4  5  1  0
  8  9  1  0
  2  1  1  0
 16 11  1  0
  9 11  1  0
  2 21  1  0
  9 10  2  0
 16 17  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 15 16  1  0
 21  8  2  0
 13 14  2  0
  3 25  1  0
 21 37  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
  7 29  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 16 33  1  0
 11 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(2S,3S)-2-(2-Hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetate	Generator

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2870 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

2-[(2S,3S)-2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

Traditional Name

[(2S,3S)-2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@]1([H])C([H])([H])C(=O)O[C@]1([H])C(=O)C1=C([H])C(=C([H])C(=C1O[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H16O6/c1-7-3-8(2)13(19)10(4-7)14(20)15-9(5-11(16)17)6-12(18)21-15/h3-4,9,15,19H,5-6H2,1-2H3,(H,16,17)/t9-,15-/m0/s1

InChI Key

XMMWCOYSUBFDCF-VFZGTOFNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Streptomyces sp. K03-0132	JEOL database	Fukuda, T., et al, J. Antibiotics 58, 252 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Xylenol
Benzoyl
M-xylene
Xylene
O-cresol
P-cresol
Aryl alkyl ketone
Phenol
Alpha-acyloxy ketone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Benzenoid
Oxolane
Vinylogous acid
Lactone
Carboxylic acid ester
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1.52	ALOGPS
logP	2.46	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.76 m³·mol⁻¹	ChemAxon
Polarizability	29.3 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44551978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fukuda, T., et al. (2005). Fukuda, T., et al, J. Antibiotics 58, 252 (2005). J. Antibiotics.

Showing NP-Card for phenatic acid B (NP0028163)

MOL for NP0028163 (phenatic acid B)

3D MOL for NP0028163 (phenatic acid B)

3D SDF for NP0028163 (phenatic acid B)

3D-SDF for NP0028163 (phenatic acid B)

PDB for NP0028163 (phenatic acid B)

3D PDB for NP0028163 (phenatic acid B)

SMILES for NP0028163 (phenatic acid B)

INCHI for NP0028163 (phenatic acid B)

Structure for NP0028163 (phenatic acid B)

3D Structure for NP0028163 (phenatic acid B)