NP-MRD: Showing NP-Card for Xanalteric acid I (NP0008813)

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Record Information

Version

2.0

Created at

2020-12-09 06:18:39 UTC

Updated at

2021-07-15 17:01:29 UTC

NP-MRD ID

NP0008813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanalteric acid I

Provided By

NPAtlas

Description

XANALTERIC ACID I is also known as xanalterate I or xanalteric acid II. Xanalteric acid I is found in Alternaria sp. Based on a literature review very few articles have been published on XANALTERIC ACID I.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 39 43  0  0  0  0            999 V2000
   -4.1902   -2.9262    0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -2.4470    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -3.2669   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.6695   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.2129   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.6190   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    0.7537   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    1.3462   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    2.7369   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    3.2798   -0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    3.5196   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    2.9576   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    1.5872   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    0.9808    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    1.7867    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    1.1791    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.1875    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -0.8197    0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.0001    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.3959    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.5616   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -0.8113   -0.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8491   -1.0094    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -2.1829    1.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    0.0756    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -1.4923   -0.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9522   -2.5067    0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -4.3409   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -3.3299   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    4.2866   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    4.6082   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.6316    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    2.8468    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434    1.7827    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2382    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -1.2598   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    0.1263    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188   -2.0248   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -3.3059   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 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
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19  2  1  0  0  0  0
 20  5  2  0  0  0  0
 26  6  1  0  0  0  0
 13  7  1  0  0  0  0
 20 14  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 22 36  1  6  0  0  0
 25 37  1  0  0  0  0
 26 38  1  6  0  0  0
 27 39  1  0  0  0  0
M  END

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
   -4.1902   -2.9262    0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -2.4470    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -3.2669   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.6695   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.2129   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.6190   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    0.7537   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    1.3462   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    2.7369   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    3.2798   -0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    3.5196   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    2.9576   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    1.5872   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    0.9808    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    1.7867    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    1.1791    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.1875    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -0.8197    0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.0001    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.3959    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.5616   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -0.8113   -0.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8491   -1.0094    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -2.1829    1.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    0.0756    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -1.4923   -0.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9522   -2.5067    0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -4.3409   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -3.3299   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    4.2866   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    4.6082   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.6316    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    2.8468    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434    1.7827    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2382    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -1.2598   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    0.1263    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188   -2.0248   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -3.3059   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 19  2  1  0
 20  5  2  0
 26  6  1  0
 13  7  1  0
 20 14  1  0
  3 28  1  0
  4 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 22 36  1  6
 25 37  1  0
 26 38  1  6
 27 39  1  0
M  END


  Mrv1652306242106303D          

 39 43  0  0  0  0            999 V2000
   -4.1902   -2.9262    0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -2.4470    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -3.2669   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.6695   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.2129   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.6190   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    0.7537   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    1.3462   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    2.7369   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    3.2798   -0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    3.5196   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    2.9576   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    1.5872   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    0.9808    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    1.7867    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    1.1791    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.1875    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -0.8197    0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.0001    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.3959    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.5616   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -0.8113   -0.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8491   -1.0094    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -2.1829    1.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    0.0756    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -1.4923   -0.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9522   -2.5067    0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -4.3409   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -3.3299   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    4.2866   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    4.6082   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.6316    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    2.8468    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434    1.7827    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2382    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -1.2598   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    0.1263    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188   -2.0248   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -3.3059   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 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
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19  2  1  0  0  0  0
 20  5  2  0  0  0  0
 26  6  1  0  0  0  0
 13  7  1  0  0  0  0
 20 14  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 22 36  1  6  0  0  0
 25 37  1  0  0  0  0
 26 38  1  6  0  0  0
 27 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])OC2=C(O[H])C([H])=C([H])C3=C4C([H])=C([H])C(O[H])=C5C(=O)C([H])=C([H])C(=C45)C(=C23)[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O7/c21-10-4-1-7-8-2-6-12(23)18-15(8)14(17(24)19(27-18)20(25)26)9-3-5-11(22)16(10)13(7)9/h1-6,17,19,21,23-24H,(H,25,26)/t17-,19+/m0/s1

> <INCHI_KEY>
SRAOLIZIJYDHTE-UHFFFAOYSA-N

> <FORMULA>
C20H12O7

> <MOLECULAR_WEIGHT>
364.309

> <EXACT_MASS>
364.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.376043199809665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-3,7,14-trihydroxy-16-oxo-5-oxapentacyclo[9.7.1.1^{2,6}.0^{15,19}.0^{10,20}]icosa-1(19),2(20),6,8,10,12,14,17-octaene-4-carboxylic acid

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.5920630526666666

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.537499713915023

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.238636725438222

> <JCHEM_PKA_STRONGEST_BASIC>
-3.620984950947551

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
94.49139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-3,7,14-trihydroxy-16-oxo-5-oxapentacyclo[9.7.1.1^{2,6}.0^{15,19}.0^{10,20}]icosa-1(19),2(20),6,8,10,12,14,17-octaene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
   -4.1902   -2.9262    0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -2.4470    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -3.2669   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.6695   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.2129   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.6190   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    0.7537   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    1.3462   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    2.7369   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    3.2798   -0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    3.5196   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    2.9576   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    1.5872   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    0.9808    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    1.7867    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    1.1791    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.1875    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -0.8197    0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.0001    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.3959    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.5616   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -0.8113   -0.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8491   -1.0094    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -2.1829    1.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    0.0756    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -1.4923   -0.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9522   -2.5067    0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -4.3409   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -3.3299   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    4.2866   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    4.6082   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.6316    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    2.8468    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434    1.7827    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2382    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -1.2598   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    0.1263    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188   -2.0248   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -3.3059   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 19  2  1  0
 20  5  2  0
 26  6  1  0
 13  7  1  0
 20 14  1  0
  3 28  1  0
  4 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 22 36  1  6
 25 37  1  0
 26 38  1  6
 27 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  O   UNK     0      -4.190  -2.926   0.422  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.042  -2.447   0.213  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.887  -3.267  -0.070  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.720  -2.670  -0.276  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.537  -1.213  -0.232  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.690  -0.619  -0.458  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.785   0.754  -0.414  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.986   1.346  -0.657  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.122   2.737  -0.633  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.370   3.280  -0.887  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.037   3.520  -0.364  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.215   2.958  -0.111  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.303   1.587  -0.144  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.535   0.981   0.085  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.623   1.787   0.347  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.847   1.179   0.565  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.958  -0.188   0.519  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.190  -0.820   0.738  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.869  -1.000   0.257  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.626  -0.396   0.035  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.090   0.562  -0.935  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.186  -0.811  -0.636  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.849  -1.009   0.697  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.021  -2.183   1.096  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.261   0.076   1.468  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.838  -1.492  -0.679  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.952  -2.507   0.320  0.00  0.00           O+0
HETATM   28  H   UNK     0      -2.005  -4.341  -0.105  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.089  -3.330  -0.498  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.459   4.287  -0.868  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.113   4.608  -0.339  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.021   3.632   0.092  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.636   2.847   0.403  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.743   1.783   0.778  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.999  -0.238   0.931  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.864  -1.260  -1.393  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.103   0.126   2.476  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.719  -2.025  -1.651  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.411  -3.306  -0.095  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   30                                                       
CONECT   11    9   12   31                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   35                                                       
CONECT   19   17   20    2                                                  
CONECT   20   19    5   14                                                  
CONECT   21    8   22                                                       
CONECT   22   21   23   26   36                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   37                                                       
CONECT   26   22   27    6   38                                             
CONECT   27   26   39                                                       
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   22                                                            
CONECT   37   25                                                            
CONECT   38   26                                                            
CONECT   39   27                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

RDKit          3D

39 43  0  0  0  0  0  0  0  0999 V2000
   -4.1902   -2.9262    0.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -2.4470    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -3.2669   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.6695   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.2129   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897   -0.6190   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    0.7537   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    1.3462   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    2.7369   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    3.2798   -0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    3.5196   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    2.9576   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    1.5872   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    0.9808    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    1.7867    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467    1.1791    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.1875    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -0.8197    0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.0001    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -0.3959    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.5616   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -0.8113   -0.6356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8491   -1.0094    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -2.1829    1.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611    0.0756    1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -1.4923   -0.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9522   -2.5067    0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053   -4.3409   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -3.3299   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    4.2866   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    4.6082   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.6316    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    2.8468    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434    1.7827    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2382    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642   -1.2598   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    0.1263    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7188   -2.0248   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -3.3059   -0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 19  2  1  0
 20  5  2  0
 26  6  1  0
 13  7  1  0
 20 14  1  0
  3 28  1  0
  4 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 22 36  1  6
 25 37  1  0
 26 38  1  6
 27 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
XANALTERate I	Generator
2,4,9-Trihydroxy-10-oxo-2,10-dihydro-1H-phenaleno(1,2,3-de)chromene-2-carboxylic acid	MeSH
1,4,9-Trihydroxy-10-oxo-2,10-dihydro-1H-phenaleno(1,2,3-de)chromene-2-carboxylic acid	MeSH
Xanalteric acid II	MeSH
3,7,14-Trihydroxy-16-oxo-5-oxapentacyclo[9.7.1.1,.0,.0,]icosa-1(19),2(20),6,8,10,12,14,17-octaene-4-carboxylate	Generator

Chemical Formula

C₂₀H₁₂O₇

Average Mass

364.3090 Da

Monoisotopic Mass

364.05830 Da

IUPAC Name

(3S,4R)-3,7,14-trihydroxy-16-oxo-5-oxapentacyclo[9.7.1.1^{2,6}.0^{15,19}.0^{10,20}]icosa-1(19),2(20),6,8,10,12,14,17-octaene-4-carboxylic acid

Traditional Name

(3S,4R)-3,7,14-trihydroxy-16-oxo-5-oxapentacyclo[9.7.1.1^{2,6}.0^{15,19}.0^{10,20}]icosa-1(19),2(20),6,8,10,12,14,17-octaene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(OC2=C3C(=CC=C2O)C2=C4C(C=CC(=O)C4=C(O)C=C2)=C13)C(O)=O

InChI Identifier

InChI=1S/C20H12O7/c21-10-4-1-7-8-2-6-12(23)18-15(8)14(17(24)19(27-18)20(25)26)9-3-5-11(22)16(10)13(7)9/h1-6,17,19,21,23-24H,(H,25,26)

InChI Key

SRAOLIZIJYDHTE-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
Alternaria sp.	NPAtlas	19835393

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenanthrols. These are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
Naphthopyran
Phenalen-1-one
Phenalen
2-naphthol
Benzopyran
Naphthalene
1-benzopyran
2-benzopyran
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Pyran
Hydroxy acid
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.25	ALOGPS
logP	2.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.49 m³·mol⁻¹	ChemAxon
Polarizability	35.38 Å³	ChemAxon
Number of Rings	5	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

NPA009060

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048234

Chemspider ID

24662944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44605530

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Xanalteric acid I (NP0008813)

MOL for NP0008813 (Xanalteric acid I)

3D MOL for NP0008813 (Xanalteric acid I)

3D SDF for NP0008813 (Xanalteric acid I)

3D-SDF for NP0008813 (Xanalteric acid I)

PDB for NP0008813 (Xanalteric acid I)

3D PDB for NP0008813 (Xanalteric acid I)

SMILES for NP0008813 (Xanalteric acid I)

INCHI for NP0008813 (Xanalteric acid I)

Structure for NP0008813 (Xanalteric acid I)

3D Structure for NP0008813 (Xanalteric acid I)