NP-MRD: Showing NP-Card for Ascochital (NP0004261)

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Record Information

Version

2.0

Created at

2020-12-09 01:46:44 UTC

Updated at

2021-07-15 16:48:42 UTC

NP-MRD ID

NP0004261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ascochital

Provided By

NPAtlas

Description

3-Formyl-2,6-dihydroxy-4-(4-methyl-3-oxohexan-2-yl)benzoic acid belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Ascochital is found in Ascochyta. Ascochital was first documented in 2002 (PMID: 12168545). Based on a literature review very few articles have been published on 3-formyl-2,6-dihydroxy-4-(4-methyl-3-oxohexan-2-yl)benzoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118053D          

 39 39  0  0  0  0            999 V2000
    3.8870    1.0278    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.2493   -0.5942 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7102   -1.2074    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4118   -1.6342    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -0.7252    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -0.5195    1.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.4978   -0.7005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3718   -1.7883   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -0.0558   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.9105   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664   -0.5612   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4226   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634    0.6846    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.0366    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.1622    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3437    2.2177    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337    1.5543    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.7959    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    1.1583    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    2.0836    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.2086    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    1.8949   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9162    1.3717   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.9488    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -0.7271   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.0184   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.1631   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -2.1208    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.8697    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -2.4601    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.2628   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.6926   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099   -1.9320   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -2.6542   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.9056   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.3278   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9079    2.9034    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    3.2664    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.8289    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19  9  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
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  6  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  7 31  1  6  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
 10 35  1  0  0  0  0
 12 36  1  0  0  0  0
 16 37  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
M  END

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    3.8870    1.0278    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.2493   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -1.2074    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4118   -1.6342    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -0.7252    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -0.5195    1.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.4978   -0.7005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3718   -1.7883   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -0.0558   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.9105   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664   -0.5612   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4226   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634    0.6846    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.0366    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.1622    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3437    2.2177    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337    1.5543    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.7959    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    1.1583    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    2.0836    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.2086    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    1.8949   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9162    1.3717   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.9488    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -0.7271   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.0184   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.1631   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -2.1208    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.8697    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -2.4601    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.2628   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.6926   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099   -1.9320   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -2.6542   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.9056   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.3278   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9079    2.9034    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    3.2664    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.8289    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  4 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 12 36  1  0
 16 37  1  0
 18 38  1  0
 20 39  1  0
M  END


  Mrv1652306242118053D          

 39 39  0  0  0  0            999 V2000
    3.8870    1.0278    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.2493   -0.5942 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7102   -1.2074    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4118   -1.6342    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -0.7252    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -0.5195    1.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.4978   -0.7005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3718   -1.7883   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -0.0558   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.9105   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664   -0.5612   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4226   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634    0.6846    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.0366    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.1622    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3437    2.2177    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337    1.5543    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.7959    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    1.1583    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    2.0836    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.2086    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    1.8949   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9162    1.3717   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.9488    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -0.7271   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.0184   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.1631   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -2.1208    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.8697    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -2.4601    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.2628   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.6926   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099   -1.9320   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -2.6542   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.9056   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.3278   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9079    2.9034    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    3.2664    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.8289    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19  9  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
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  6  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  7 31  1  6  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
 10 35  1  0  0  0  0
 12 36  1  0  0  0  0
 16 37  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004261

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O6/c1-4-7(2)13(18)8(3)9-5-11(17)12(15(20)21)14(19)10(9)6-16/h5-8,17,19H,4H2,1-3H3,(H,20,21)/t7-,8+/m1/s1

> <INCHI_KEY>
BUBGGXXWUJXFLO-UHFFFAOYSA-N

> <FORMULA>
C15H18O6

> <MOLECULAR_WEIGHT>
294.303

> <EXACT_MASS>
294.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.841919883716457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-formyl-2,6-dihydroxy-4-[(2S,4R)-4-methyl-3-oxohexan-2-yl]benzoic acid

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
4.884651306

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.45433822544414

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3444858074507482

> <JCHEM_PKA_STRONGEST_BASIC>
-6.034930857361087

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
77.09560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-formyl-2,6-dihydroxy-4-[(2S,4R)-4-methyl-3-oxohexan-2-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    3.8870    1.0278    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.2493   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -1.2074    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4118   -1.6342    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -0.7252    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -0.5195    1.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.4978   -0.7005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3718   -1.7883   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -0.0558   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.9105   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664   -0.5612   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4226   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634    0.6846    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.0366    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.1622    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3437    2.2177    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337    1.5543    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.7959    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    1.1583    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    2.0836    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.2086    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    1.8949   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9162    1.3717   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.9488    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -0.7271   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.0184   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.1631   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -2.1208    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.8697    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -2.4601    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.2628   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.6926   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099   -1.9320   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -2.6542   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.9056   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.3278   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9079    2.9034    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    3.2664    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.8289    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
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  3 27  1  6
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  4 29  1  0
  4 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 12 36  1  0
 16 37  1  0
 18 38  1  0
 20 39  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       3.887   1.028   0.074  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.517  -0.249  -0.594  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.710  -1.207   0.232  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.412  -1.634   1.494  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.328  -0.725   0.434  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.936  -0.520   1.559  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.437  -0.498  -0.701  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.372  -1.788  -1.534  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.911  -0.056  -0.366  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.970  -0.911  -0.587  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.266  -0.561  -0.281  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.327  -1.423  -0.504  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.563   0.685   0.271  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.935   1.037   0.586  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.835   0.162   0.337  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.344   2.218   1.124  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.534   1.554   0.501  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.683   2.796   1.032  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.205   1.158   0.171  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.123   2.084   0.406  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.367   3.209   0.893  0.00  0.00           O+0
HETATM   22  H   UNK     0       3.239   1.895  -0.165  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.916   1.372  -0.253  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.970   0.949   1.178  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.445  -0.727  -0.997  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.927   0.018  -1.513  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.681  -2.163  -0.391  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.357  -2.121   1.210  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.505  -0.870   2.263  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.778  -2.460   1.934  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.866   0.263  -1.419  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.332  -1.693  -2.379  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.410  -1.932  -1.962  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.099  -2.654  -0.931  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.783  -1.906  -1.016  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.115  -2.328  -0.904  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.908   2.903   0.664  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.475   3.266   1.324  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.885   1.829   0.173  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3   25   26                                             
CONECT    3    2    4    5   27                                             
CONECT    4    3   28   29   30                                             
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   31                                             
CONECT    8    7   32   33   34                                             
CONECT    9    7   10   19                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   36                                                       
CONECT   13   11   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   37                                                       
CONECT   17   13   18   19                                                  
CONECT   18   17   38                                                       
CONECT   19   17   20    9                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   16                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

RDKit          3D

39 39  0  0  0  0  0  0  0  0999 V2000
    3.8870    1.0278    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.2493   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -1.2074    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4118   -1.6342    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -0.7252    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356   -0.5195    1.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.4978   -0.7005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3718   -1.7883   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -0.0558   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.9105   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2664   -0.5612   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4226   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634    0.6846    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.0366    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.1622    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3437    2.2177    1.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337    1.5543    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.7959    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    1.1583    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    2.0836    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.2086    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    1.8949   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9162    1.3717   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.9488    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -0.7271   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.0184   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.1631   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -2.1208    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053   -0.8697    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -2.4601    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.2628   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.6926   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099   -1.9320   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -2.6542   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.9056   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.3278   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9079    2.9034    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    3.2664    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.8289    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
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 20 21  2  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  4 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 12 36  1  0
 16 37  1  0
 18 38  1  0
 20 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-Formyl-2,6-dihydroxy-4-(4-methyl-3-oxohexan-2-yl)benzoate	Generator

Chemical Formula

C₁₅H₁₈O₆

Average Mass

294.3030 Da

Monoisotopic Mass

294.11034 Da

IUPAC Name

3-formyl-2,6-dihydroxy-4-[(2S,4R)-4-methyl-3-oxohexan-2-yl]benzoic acid

Traditional Name

3-formyl-2,6-dihydroxy-4-[(2S,4R)-4-methyl-3-oxohexan-2-yl]benzoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)C(C)C1=CC(O)=C(C(O)=O)C(O)=C1C=O

InChI Identifier

InChI=1S/C15H18O6/c1-4-7(2)13(18)8(3)9-5-11(17)12(15(20)21)14(19)10(9)6-16/h5-8,17,19H,4H2,1-3H3,(H,20,21)

InChI Key

BUBGGXXWUJXFLO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ascochyta	NPAtlas	12168545

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Hydroxybenzoic acid
Monocyclic monoterpenoid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Hydroxybenzaldehyde
Resorcinol
Benzaldehyde
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
Aryl-aldehyde
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid
Carboxylic acid derivative
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.74	ALOGPS
logP	4.88	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.34	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.1 m³·mol⁻¹	ChemAxon
Polarizability	29.84 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

NPA012095

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8170164

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9994583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kusnick C, Jansen R, Liberra K, Lindequist U: Ascochital, a new metabolite from the marine ascomycete Kirschsteiniothelia maritima. Pharmazie. 2002 Jul;57(7):510-2. [PubMed:12168545 ]

Showing NP-Card for Ascochital (NP0004261)

MOL for NP0004261 (Ascochital)

3D MOL for NP0004261 (Ascochital)

3D SDF for NP0004261 (Ascochital)

3D-SDF for NP0004261 (Ascochital)

PDB for NP0004261 (Ascochital)

3D PDB for NP0004261 (Ascochital)

SMILES for NP0004261 (Ascochital)

INCHI for NP0004261 (Ascochital)

Structure for NP0004261 (Ascochital)

3D Structure for NP0004261 (Ascochital)