NP-MRD: Showing NP-Card for Paradictyoarthrin B (NP0013479)

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Record Information

Version

1.0

Created at

2021-01-05 22:49:44 UTC

Updated at

2021-07-15 17:14:36 UTC

NP-MRD ID

NP0013479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paradictyoarthrin B

Provided By

NPAtlas

Description

Auxarthrol A belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Paradictyoarthrin B is found in Paradictyoarthrinium and Paradictyoarthrinium diffractum. It was first documented in 2015 (PMID: 25407145). Based on a literature review very few articles have been published on Auxarthrol A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119363D          

 40 43  0  0  0  0            999 V2000
    6.3719   -1.0259   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -1.6666   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -0.9133   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4386    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.2493    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    2.6024    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.5815    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.8119    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.5300    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622   -1.3902    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -2.5739    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -0.6216    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2514   -1.3446    0.1846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4755   -0.5018    0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2037   -0.5104    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.0663   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.9162   -0.2607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3856    1.6582   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.4782    0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.2473    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    0.7333    0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9178    0.1026   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.2844    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    2.3903    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.2501   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -1.7675   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661   -0.5276    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    0.9293   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    3.2620    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   -2.6106    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -2.1700   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964   -1.9037    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058   -0.9780    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.1250    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.5263    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.9454   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8739   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.3326   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    2.5665    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.0616    2.4034 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
  9  3  1  0  0  0  0
 21 12  1  0  0  0  0
 23  7  1  0  0  0  0
 12 22  1  6  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  4 28  1  0  0  0  0
  6 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  1  0  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    6.3719   -1.0259   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -1.6666   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -0.9133   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4386    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.2493    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    2.6024    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.5815    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.8119    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.5300    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622   -1.3902    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -2.5739    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -0.6216    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2514   -1.3446    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755   -0.5018    0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2037   -0.5104    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.0663   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.9162   -0.2607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3856    1.6582   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.4782    0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.2473    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    0.7333    0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9178    0.1026   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.2844    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    2.3903    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.2501   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -1.7675   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661   -0.5276    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    0.9293   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    3.2620    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   -2.6106    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -2.1700   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964   -1.9037    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058   -0.9780    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.1250    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.5263    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.9454   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8739   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.3326   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    2.5665    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.0616    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
  9  3  1  0
 21 12  1  0
 23  7  1  0
 12 22  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  1
 20 40  1  0
M  END


  Mrv1652306242119363D          

 40 43  0  0  0  0            999 V2000
    6.3719   -1.0259   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -1.6666   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -0.9133   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4386    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.2493    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    2.6024    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.5815    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.8119    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.5300    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622   -1.3902    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -2.5739    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -0.6216    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2514   -1.3446    0.1846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4755   -0.5018    0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2037   -0.5104    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.0663   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.9162   -0.2607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3856    1.6582   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.4782    0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.2473    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    0.7333    0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9178    0.1026   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.2844    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    2.3903    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.2501   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -1.7675   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661   -0.5276    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    0.9293   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    3.2620    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   -2.6106    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -2.1700   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964   -1.9037    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058   -0.9780    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.1250    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.5263    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.9454   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8739   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.3326   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    2.5665    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.0616    2.4034 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
  9  3  1  0  0  0  0
 21 12  1  0  0  0  0
 23  7  1  0  0  0  0
 12 22  1  6  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  4 28  1  0  0  0  0
  6 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  1  0  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C([H])C(OC([H])([H])[H])=C1[H])C(=O)[C@]13O[C@@]1(C2=O)[C@]([H])(O[H])[C@]([H])(O[H])[C@](O[H])(C([H])([H])[H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-14(22)5-15-10(18)7-3-6(23-2)4-8(17)9(7)11(19)16(15,24-15)13(21)12(14)20/h3-4,12-13,17,20-22H,5H2,1-2H3/t12-,13+,14-,15-,16-/m0/s1

> <INCHI_KEY>
UCEZSAYKHGKFBH-QRJUGERDSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08651754150088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,10R,12S,13S,14R)-4,12,13,14-tetrahydroxy-6-methoxy-12-methyl-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3,5,7-triene-2,9-dione

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-0.5131781209999995

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.477954577947227

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.946451193068176

> <JCHEM_PKA_STRONGEST_BASIC>
-3.297812193533672

> <JCHEM_POLAR_SURFACE_AREA>
136.82000000000002

> <JCHEM_REFRACTIVITY>
78.07509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,12S,13S,14R)-4,12,13,14-tetrahydroxy-6-methoxy-12-methyl-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3,5,7-triene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    6.3719   -1.0259   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -1.6666   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -0.9133   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4386    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.2493    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    2.6024    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.5815    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.8119    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.5300    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622   -1.3902    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -2.5739    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -0.6216    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2514   -1.3446    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755   -0.5018    0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2037   -0.5104    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.0663   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.9162   -0.2607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3856    1.6582   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.4782    0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.2473    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    0.7333    0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9178    0.1026   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.2844    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    2.3903    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.2501   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -1.7675   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661   -0.5276    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    0.9293   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    3.2620    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   -2.6106    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -2.1700   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964   -1.9037    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058   -0.9780    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.1250    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.5263    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.9454   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8739   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.3326   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    2.5665    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.0616    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
  9  3  1  0
 21 12  1  0
 23  7  1  0
 12 22  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  1
 20 40  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       6.372  -1.026  -0.323  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.130  -1.667  -0.214  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.959  -0.913  -0.044  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.025   0.439   0.016  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.891   1.249   0.185  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.017   2.602   0.236  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.696   0.582   0.288  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.589  -0.812   0.229  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.739  -1.530   0.063  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.262  -1.390   0.344  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.187  -2.574   0.736  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.970  -0.622   0.013  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.251  -1.345   0.185  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.475  -0.502   0.175  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.204  -0.510   1.508  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.365  -1.066  -0.769  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.243   0.916  -0.261  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.386   1.658  -0.155  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.068   1.478   0.503  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.160   1.247   1.868  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.845   0.733   0.007  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.918   0.103  -1.234  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.434   1.284   0.480  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.463   2.390   1.071  0.00  0.00           O+0
HETATM   25  H   UNK     0       6.297  -0.250  -1.131  0.00  0.00           H+0
HETATM   26  H   UNK     0       7.138  -1.768  -0.643  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.666  -0.528   0.612  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.999   0.929  -0.070  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.304   3.262   0.334  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.651  -2.611   0.020  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.282  -2.170  -0.586  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.196  -1.904   1.164  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.206  -0.978   1.440  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.632  -1.125   2.244  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.383   0.526   1.887  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.623  -1.945  -0.389  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.932   0.874  -1.339  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.378   2.333  -0.905  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.006   2.567   0.302  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.294   2.062   2.403  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   29                                                       
CONECT    7    5    8   23                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3   30                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21   22                                             
CONECT   13   12   14   31   32                                             
CONECT   14   13   15   16   17                                             
CONECT   15   14   33   34   35                                             
CONECT   16   14   36                                                       
CONECT   17   14   18   19   37                                             
CONECT   18   17   38                                                       
CONECT   19   17   20   21   39                                             
CONECT   20   19   40                                                       
CONECT   21   19   22   23   12                                             
CONECT   22   21   12                                                       
CONECT   23   21   24    7                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    6                                                            
CONECT   30    9                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

RDKit          3D

40 43  0  0  0  0  0  0  0  0999 V2000
    6.3719   -1.0259   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -1.6666   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -0.9133   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4386    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    1.2493    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    2.6024    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.5815    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -0.8119    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.5300    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622   -1.3902    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -2.5739    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -0.6216    0.0126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2514   -1.3446    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755   -0.5018    0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2037   -0.5104    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.0663   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.9162   -0.2607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3856    1.6582   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.4782    0.5029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.2473    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    0.7333    0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9178    0.1026   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.2844    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    2.3903    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.2501   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -1.7675   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661   -0.5276    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    0.9293   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    3.2620    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   -2.6106    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -2.1700   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964   -1.9037    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058   -0.9780    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.1250    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835    0.5263    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.9454   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8739   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.3326   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    2.5665    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    2.0616    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
  9  3  1  0
 21 12  1  0
 23  7  1  0
 12 22  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  1
 20 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₈

Average Mass

336.2960 Da

Monoisotopic Mass

336.08452 Da

IUPAC Name

(1S,10R,12S,13S,14R)-4,12,13,14-tetrahydroxy-6-methoxy-12-methyl-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3,5,7-triene-2,9-dione

Traditional Name

(1S,10R,12S,13S,14R)-4,12,13,14-tetrahydroxy-6-methoxy-12-methyl-15-oxatetracyclo[8.4.1.0^{1,10}.0^{3,8}]pentadeca-3,5,7-triene-2,9-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)[C@@]34O[C@@]3(C[C@](C)(O)[C@@H](O)[C@H]4O)C(=O)C2=C1

InChI Identifier

InChI=1S/C16H16O8/c1-14(22)5-15-10(18)7-3-6(23-2)4-8(17)9(7)11(19)16(15,24-15)13(21)12(14)20/h3-4,12-13,17,20-22H,5H2,1-2H3/t12-,13+,14-,15-,16-/m0/s1

InChI Key

UCEZSAYKHGKFBH-QRJUGERDSA-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
Paradictyoarthrinium	NPAtlas	25407145
Paradictyoarthrinium diffractum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
Anisole
Oxepane
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Cyclitol or derivatives
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Ketone
Secondary alcohol
Oxacycle
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	0.43	ALOGPS
logP	-0.51	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.08 m³·mol⁻¹	ChemAxon
Polarizability	32.09 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017537

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35517007

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101342817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Isaka M, Chinthanom P, Rachtawee P, Srichomthong K, Srikitikulchai P, Kongsaeree P, Prabpai S: Cytotoxic hydroanthraquinones from the mangrove-derived fungus Paradictyoarthrinium diffractum BCC 8704. J Antibiot (Tokyo). 2015 May;68(5):334-8. doi: 10.1038/ja.2014.153. Epub 2014 Nov 19. [PubMed:25407145 ]

Showing NP-Card for Paradictyoarthrin B (NP0013479)

MOL for NP0013479 (Paradictyoarthrin B)

3D MOL for NP0013479 (Paradictyoarthrin B)

3D SDF for NP0013479 (Paradictyoarthrin B)

3D-SDF for NP0013479 (Paradictyoarthrin B)

PDB for NP0013479 (Paradictyoarthrin B)

3D PDB for NP0013479 (Paradictyoarthrin B)

SMILES for NP0013479 (Paradictyoarthrin B)

INCHI for NP0013479 (Paradictyoarthrin B)

Structure for NP0013479 (Paradictyoarthrin B)

3D Structure for NP0013479 (Paradictyoarthrin B)