NP-MRD: Showing NP-Card for Xylacinic acid B (NP0011008)

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Record Information

Version

2.0

Created at

2021-01-05 20:47:20 UTC

Updated at

2021-07-15 17:07:42 UTC

NP-MRD ID

NP0011008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xylacinic acid B

Provided By

NPAtlas

Description

Xylacinic acid B is found in Xylaria and Xylaria cubensis. Based on a literature review very few articles have been published on (2E)-2-[(2R)-1-methoxy-1-oxopropan-2-yl]octa-2,7-dienoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107433D          

 34 33  0  0  0  0            999 V2000
   -5.6290    0.2186   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -0.3526   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -0.1416   -1.1167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3436    0.4937   -0.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9438    0.6725   -0.6828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1160    1.2729    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270    0.8061    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.6703    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031    2.7945    2.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    1.1280    2.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.4852    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949   -1.5860   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -0.2857    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882    0.8824   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -1.3279   -0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.0928   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316    0.0591   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5436    0.8539   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.9875    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287    0.5747   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -1.0826   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4577    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.2524    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    1.4935   -1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -0.2311   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    2.3107    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381    0.6947    3.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.9075    1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -1.8507    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -1.6198   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -2.5732    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.1064   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -1.8535   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -1.0690    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 12 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
M  END

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -5.6290    0.2186   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -0.3526   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -0.1416   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    0.4937   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438    0.6725   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    1.2729    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270    0.8061    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.6703    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031    2.7945    2.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    1.1280    2.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.4852    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949   -1.5860   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -0.2857    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882    0.8824   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -1.3279   -0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.0928   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316    0.0591   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5436    0.8539   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.9875    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287    0.5747   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -1.0826   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4577    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.2524    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    1.4935   -1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -0.2311   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    2.3107    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381    0.6947    3.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.9075    1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -1.8507    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -1.6198   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -2.5732    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.1064   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -1.8535   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -1.0690    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 12 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END


  Mrv1652306242107433D          

 34 33  0  0  0  0            999 V2000
   -5.6290    0.2186   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -0.3526   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -0.1416   -1.1167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3436    0.4937   -0.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9438    0.6725   -0.6828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1160    1.2729    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270    0.8061    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.6703    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031    2.7945    2.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    1.1280    2.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.4852    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949   -1.5860   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -0.2857    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882    0.8824   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -1.3279   -0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.0928   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316    0.0591   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5436    0.8539   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.9875    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287    0.5747   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -1.0826   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4577    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.2524    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    1.4935   -1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -0.2311   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    2.3107    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381    0.6947    3.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.9075    1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -1.8507    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -1.6198   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -2.5732    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.1064   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -1.8535   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -1.0690    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 12 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4/c1-4-5-6-7-8-10(11(13)14)9(2)12(15)16-3/h4,8-9H,1,5-7H2,2-3H3,(H,13,14)/b10-8+/t9-/m1/s1

> <INCHI_KEY>
MUHHFBJAEXVAPF-NCXKZPMSSA-N

> <FORMULA>
C12H18O4

> <MOLECULAR_WEIGHT>
226.272

> <EXACT_MASS>
226.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.861628832408066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[(2R)-1-methoxy-1-oxopropan-2-yl]octa-2,7-dienoic acid

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.6026266846666664

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.672988461288072

> <JCHEM_PKA_STRONGEST_BASIC>
-7.115661150249025

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
61.380100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[(2R)-1-methoxy-1-oxopropan-2-yl]octa-2,7-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -5.6290    0.2186   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -0.3526   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -0.1416   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    0.4937   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438    0.6725   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    1.2729    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270    0.8061    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.6703    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031    2.7945    2.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    1.1280    2.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.4852    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949   -1.5860   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -0.2857    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882    0.8824   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -1.3279   -0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.0928   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316    0.0591   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5436    0.8539   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.9875    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287    0.5747   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -1.0826   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4577    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.2524    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    1.4935   -1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -0.2311   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    2.3107    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381    0.6947    3.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.9075    1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -1.8507    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -1.6198   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -2.5732    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.1064   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -1.8535   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -1.0690    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 12 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  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      -5.629   0.219  -1.170  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.585  -0.353  -0.594  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.214  -0.142  -1.117  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.344   0.494  -0.047  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.944   0.673  -0.683  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.116   1.273   0.324  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.927   0.806   0.908  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.622   1.670   1.947  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.203   2.795   2.232  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.734   1.128   2.543  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.515  -0.485   0.729  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.895  -1.586  -0.012  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.907  -0.286   0.176  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.288   0.882  -0.020  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.761  -1.328  -0.115  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.059  -1.093  -0.632  0.00  0.00           C+0
HETATM   17  H   UNK     0      -6.632   0.059  -0.781  0.00  0.00           H+0
HETATM   18  H   UNK     0      -5.544   0.854  -2.030  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.711  -0.988   0.273  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.229   0.575  -1.978  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.712  -1.083  -1.418  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.731   1.458   0.304  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.264  -0.252   0.772  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.207   1.494  -1.472  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.707  -0.231  -1.183  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.410   2.311   0.667  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.738   0.695   3.458  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.745  -0.908   1.802  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.147  -1.851   0.285  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.078  -1.620  -1.114  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.434  -2.573   0.297  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.097  -0.106  -1.139  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.304  -1.853  -1.399  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.814  -1.069   0.189  0.00  0.00           H+0
CONECT    1    2   17   18                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   22   23                                             
CONECT    5    4    6   24   25                                             
CONECT    6    5    7   26                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   27                                                       
CONECT   11    7   12   13   28                                             
CONECT   12   11   29   30   31                                             
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   32   33   34                                             
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   12                                                            
CONECT   31   12                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

RDKit          3D

34 33  0  0  0  0  0  0  0  0999 V2000
   -5.6290    0.2186   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847   -0.3526   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -0.1416   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    0.4937   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438    0.6725   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    1.2729    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270    0.8061    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.6703    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031    2.7945    2.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    1.1280    2.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.4852    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949   -1.5860   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -0.2857    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2882    0.8824   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -1.3279   -0.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.0928   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316    0.0591   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5436    0.8539   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.9875    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287    0.5747   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116   -1.0826   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4577    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -0.2524    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    1.4935   -1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -0.2311   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    2.3107    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381    0.6947    3.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.9075    1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -1.8507    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -1.6198   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -2.5732    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.1064   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -1.8535   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -1.0690    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 12 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E)-2-[(2R)-1-Methoxy-1-oxopropan-2-yl]octa-2,7-dienoate	Generator
Xylacinate b	Generator

Chemical Formula

C₁₂H₁₈O₄

Average Mass

226.2720 Da

Monoisotopic Mass

226.12051 Da

IUPAC Name

(2E)-2-[(2R)-1-methoxy-1-oxopropan-2-yl]octa-2,7-dienoic acid

Traditional Name

(2E)-2-[(2R)-1-methoxy-1-oxopropan-2-yl]octa-2,7-dienoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](C)C(=C/CCCC=C)\C(O)=O

InChI Identifier

InChI=1S/C12H18O4/c1-4-5-6-7-8-10(11(13)14)9(2)12(15)16-3/h4,8-9H,1,5-7H2,2-3H3,(H,13,14)/b10-8+/t9-/m1/s1

InChI Key

MUHHFBJAEXVAPF-NCXKZPMSSA-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
Xylaria	NPAtlas	22864733
Xylaria cubensis	LOTUS Database	35616633

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	2.48	ALOGPS
logP	2.6	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	61.38 m³·mol⁻¹	ChemAxon
Polarizability	24.86 Å³	ChemAxon
Number of Rings	0	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

NPA010175

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29215005

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Xylacinic acid B (NP0011008)

MOL for NP0011008 (Xylacinic acid B)

3D MOL for NP0011008 (Xylacinic acid B)

3D SDF for NP0011008 (Xylacinic acid B)

3D-SDF for NP0011008 (Xylacinic acid B)

PDB for NP0011008 (Xylacinic acid B)

3D PDB for NP0011008 (Xylacinic acid B)

SMILES for NP0011008 (Xylacinic acid B)

INCHI for NP0011008 (Xylacinic acid B)

Structure for NP0011008 (Xylacinic acid B)

3D Structure for NP0011008 (Xylacinic acid B)