NP-MRD: Showing NP-Card for altersolanol A (NP0034377)

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Record Information

Version

1.0

Created at

2021-06-20 18:07:27 UTC

Updated at

2021-06-30 00:04:43 UTC

NP-MRD ID

NP0034377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

altersolanol A

Provided By

JEOL Database JEOL Logo

Description

altersolanol A is found in Alternaria porri, Alternaria solani, Ampelomyces sp., Dactylaria lutea, Mentha pulegium and Stemphylium botryosum. It was first documented in 2009 (Debbab, A., et al.). Based on a literature review very few articles have been published on (1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120073D          

 40 42  0  0  0  0            999 V2000
   -0.3454   -4.7540   -5.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -4.6632   -4.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -3.6452   -3.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.6853   -4.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6969   -4.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -0.7970   -4.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.6521   -2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -2.6096   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -3.6041   -2.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -2.5937   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -3.4749    0.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.4946    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.5861   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.6125   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.2198   -2.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.5235    0.0712 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223    0.6301   -0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3484    1.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7980    1.6227    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1259    2.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4006   -0.2444    3.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.8724    2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.4746    1.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4646   -2.5497    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -5.6136   -5.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -3.8621   -6.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -4.9293   -6.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773   -2.6765   -5.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.1601   -4.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -4.3562   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.4806   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    0.7823   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.3510    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.8665    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.9213    4.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -0.6133    4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    0.7315    4.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    1.7094    2.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.6563    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -3.3672    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
  8  9  1  0  0  0  0
 20 23  1  0  0  0  0
 23 12  1  0  0  0  0
  4  5  2  0  0  0  0
 20 22  1  1  0  0  0
  8 10  1  0  0  0  0
 18 19  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 13  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  0  0  0  0
 16 17  1  0  0  0  0
  9  3  2  0  0  0  0
 23 24  1  0  0  0  0
  3  4  1  0  0  0  0
 20 21  1  0  0  0  0
 12 13  2  0  0  0  0
  3  2  1  0  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
 13 16  1  0  0  0  0
  5  6  1  0  0  0  0
  4 28  1  0  0  0  0
  9 30  1  0  0  0  0
 16 31  1  1  0  0  0
 18 33  1  6  0  0  0
 23 39  1  1  0  0  0
 22 38  1  0  0  0  0
 19 34  1  0  0  0  0
 17 32  1  0  0  0  0
 24 40  1  0  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.3454   -4.7540   -5.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -4.6632   -4.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -3.6452   -3.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.6853   -4.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6969   -4.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -0.7970   -4.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.6521   -2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -2.6096   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -3.6041   -2.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -2.5937   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -3.4749    0.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.4946    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.5861   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.6125   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.2198   -2.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.5235    0.0712 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223    0.6301   -0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3484    1.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7980    1.6227    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1259    2.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4006   -0.2444    3.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.8724    2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.4746    1.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4646   -2.5497    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -5.6136   -5.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -3.8621   -6.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -4.9293   -6.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773   -2.6765   -5.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.1601   -4.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -4.3562   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.4806   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    0.7823   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.3510    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.8665    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.9213    4.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -0.6133    4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    0.7315    4.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    1.7094    2.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.6563    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -3.3672    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 16 18  1  0
 18 20  1  0
  8  9  1  0
 20 23  1  0
 23 12  1  0
  4  5  2  0
 20 22  1  1
  8 10  1  0
 18 19  1  0
  7 14  1  0
 14 15  2  0
 14 13  1  0
 10 11  2  0
 12 10  1  0
 16 17  1  0
  9  3  2  0
 23 24  1  0
  3  4  1  0
 20 21  1  0
 12 13  2  0
  3  2  1  0
  8  7  2  0
  2  1  1  0
 13 16  1  0
  5  6  1  0
  4 28  1  0
  9 30  1  0
 16 31  1  1
 18 33  1  6
 23 39  1  1
 22 38  1  0
 19 34  1  0
 17 32  1  0
 24 40  1  0
 21 35  1  0
 21 36  1  0
 21 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 29  1  0
M  END


  Mrv1652306202120073D          

 40 42  0  0  0  0            999 V2000
   -0.3454   -4.7540   -5.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -4.6632   -4.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -3.6452   -3.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.6853   -4.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6969   -4.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -0.7970   -4.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.6521   -2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -2.6096   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -3.6041   -2.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -2.5937   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -3.4749    0.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.4946    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.5861   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.6125   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.2198   -2.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.5235    0.0712 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223    0.6301   -0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3484    1.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7980    1.6227    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1259    2.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4006   -0.2444    3.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.8724    2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.4746    1.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4646   -2.5497    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -5.6136   -5.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -3.8621   -6.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -4.9293   -6.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773   -2.6765   -5.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.1601   -4.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -4.3562   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.4806   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    0.7823   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.3510    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.8665    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.9213    4.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -0.6133    4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    0.7315    4.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    1.7094    2.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.6563    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -3.3672    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
  8  9  1  0  0  0  0
 20 23  1  0  0  0  0
 23 12  1  0  0  0  0
  4  5  2  0  0  0  0
 20 22  1  1  0  0  0
  8 10  1  0  0  0  0
 18 19  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 13  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  0  0  0  0
 16 17  1  0  0  0  0
  9  3  2  0  0  0  0
 23 24  1  0  0  0  0
  3  4  1  0  0  0  0
 20 21  1  0  0  0  0
 12 13  2  0  0  0  0
  3  2  1  0  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
 13 16  1  0  0  0  0
  5  6  1  0  0  0  0
  4 28  1  0  0  0  0
  9 30  1  0  0  0  0
 16 31  1  1  0  0  0
 18 33  1  6  0  0  0
 23 39  1  1  0  0  0
 22 38  1  0  0  0  0
 19 34  1  0  0  0  0
 17 32  1  0  0  0  0
 24 40  1  0  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C1C(=O)C1=C(C2=O)[C@@]([H])(O[H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-16(23)14(21)10-9(13(20)15(16)22)12(19)8-6(11(10)18)3-5(24-2)4-7(8)17/h3-4,13-15,17,20-23H,1-2H3/t13-,14+,15+,16-/m0/s1

> <INCHI_KEY>
VSMBLBOUQJNJIL-JJXSEGSLSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.616772454908684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-1.119443990333334

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.423930463544302

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.128201819403442

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5657305844301677

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
80.82550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
altersolanol A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.3454   -4.7540   -5.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -4.6632   -4.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -3.6452   -3.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.6853   -4.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6969   -4.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -0.7970   -4.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.6521   -2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -2.6096   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -3.6041   -2.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -2.5937   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -3.4749    0.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.4946    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.5861   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.6125   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.2198   -2.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.5235    0.0712 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223    0.6301   -0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3484    1.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7980    1.6227    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1259    2.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4006   -0.2444    3.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.8724    2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.4746    1.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4646   -2.5497    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -5.6136   -5.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -3.8621   -6.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -4.9293   -6.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773   -2.6765   -5.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.1601   -4.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -4.3562   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.4806   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    0.7823   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.3510    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.8665    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.9213    4.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -0.6133    4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    0.7315    4.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    1.7094    2.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.6563    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -3.3672    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 16 18  1  0
 18 20  1  0
  8  9  1  0
 20 23  1  0
 23 12  1  0
  4  5  2  0
 20 22  1  1
  8 10  1  0
 18 19  1  0
  7 14  1  0
 14 15  2  0
 14 13  1  0
 10 11  2  0
 12 10  1  0
 16 17  1  0
  9  3  2  0
 23 24  1  0
  3  4  1  0
 20 21  1  0
 12 13  2  0
  3  2  1  0
  8  7  2  0
  2  1  1  0
 13 16  1  0
  5  6  1  0
  4 28  1  0
  9 30  1  0
 16 31  1  1
 18 33  1  6
 23 39  1  1
 22 38  1  0
 19 34  1  0
 17 32  1  0
 24 40  1  0
 21 35  1  0
 21 36  1  0
 21 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 29  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.345  -4.754  -5.642  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.135  -4.663  -4.237  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.661  -3.645  -3.794  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.284  -2.685  -4.590  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.075  -1.697  -4.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.649  -0.797  -4.859  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.253  -1.652  -2.612  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.630  -2.610  -1.819  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.837  -3.604  -2.408  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.800  -2.594  -0.355  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.318  -3.475   0.347  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.593  -1.495   0.249  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.223  -0.586  -0.513  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.089  -0.613  -1.989  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.660   0.220  -2.691  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.056   0.524   0.071  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.322   0.630  -0.594  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.364   0.348   1.575  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.798   1.623   2.095  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.120  -0.126   2.346  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.401  -0.244   3.850  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.088   0.872   2.192  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.620  -1.475   1.758  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.465  -2.550   2.172  0.00  0.00           O+0
HETATM   25  H   UNK     0      -0.997  -5.614  -5.827  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.854  -3.862  -6.023  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.597  -4.929  -6.171  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.177  -2.676  -5.670  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.187  -0.160  -4.337  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.350  -4.356  -1.789  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.543   1.481  -0.087  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.122   0.782  -1.542  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.198  -0.351   1.720  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.574   1.867   1.551  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.235  -0.921   4.059  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.513  -0.613   4.377  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.633   0.732   4.291  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.496   1.709   2.497  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.611  -1.656   2.150  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.954  -3.367   2.001  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    9    4    2                                                  
CONECT    4    5    3   28                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   29                                                       
CONECT    7    5   14    8                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8    3   30                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   23   10   13                                                  
CONECT   13   14   12   16                                                  
CONECT   14    7   15   13                                                  
CONECT   15   14                                                            
CONECT   16   18   17   13   31                                             
CONECT   17   16   32                                                       
CONECT   18   16   20   19   33                                             
CONECT   19   18   34                                                       
CONECT   20   18   23   22   21                                             
CONECT   21   20   35   36   37                                             
CONECT   22   20   38                                                       
CONECT   23   20   12   24   39                                             
CONECT   24   23   40                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    6                                                            
CONECT   30    9                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
CONECT   35   21                                                            
CONECT   36   21                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
   -0.3454   -4.7540   -5.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -4.6632   -4.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -3.6452   -3.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.6853   -4.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6969   -4.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -0.7970   -4.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -1.6521   -2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -2.6096   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -3.6041   -2.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -2.5937   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -3.4749    0.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.4946    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.5861   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.6125   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.2198   -2.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.5235    0.0712 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223    0.6301   -0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3484    1.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7980    1.6227    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201   -0.1259    2.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4006   -0.2444    3.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.8724    2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.4746    1.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4646   -2.5497    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -5.6136   -5.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537   -3.8621   -6.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -4.9293   -6.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773   -2.6765   -5.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.1601   -4.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -4.3562   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.4806   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    0.7823   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -0.3510    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    1.8665    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.9213    4.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -0.6133    4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    0.7315    4.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    1.7094    2.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.6563    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -3.3672    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 16 18  1  0
 18 20  1  0
  8  9  1  0
 20 23  1  0
 23 12  1  0
  4  5  2  0
 20 22  1  1
  8 10  1  0
 18 19  1  0
  7 14  1  0
 14 15  2  0
 14 13  1  0
 10 11  2  0
 12 10  1  0
 16 17  1  0
  9  3  2  0
 23 24  1  0
  3  4  1  0
 20 21  1  0
 12 13  2  0
  3  2  1  0
  8  7  2  0
  2  1  1  0
 13 16  1  0
  5  6  1  0
  4 28  1  0
  9 30  1  0
 16 31  1  1
 18 33  1  6
 23 39  1  1
 22 38  1  0
 19 34  1  0
 17 32  1  0
 24 40  1  0
 21 35  1  0
 21 36  1  0
 21 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
As-a 2	MeSH

Chemical Formula

C₁₆H₁₆O₈

Average Mass

336.2960 Da

Monoisotopic Mass

336.08452 Da

IUPAC Name

(1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

Traditional Name

altersolanol A

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C1C(=O)C1=C(C2=O)[C@@]([H])(O[H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C16H16O8/c1-16(23)14(21)10-9(13(20)15(16)22)12(19)8-6(11(10)18)3-5(24-2)4-7(8)17/h3-4,13-15,17,20-23H,1-2H3/t13-,14+,15+,16-/m0/s1

InChI Key

VSMBLBOUQJNJIL-JJXSEGSLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria porri	LOTUS Database	35616633
Alternaria solani	LOTUS Database	35616633
Ampelomyces sp.	-	KNApSAcK
Dactylaria lutea	-	KNApSAcK
Dactylis lutea	KNApSAcK Database	22123792
Mentha pulegium	JEOL database	Debbab, A., et al, J. Nat. Prod. 72, 626 (2009)
Stemphylium botryosum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Cladosporium sp.	KNApSAcK Database	22123792
Phomopsis juniperovora	KNApSAcK Database	22123792
Stemphylium botryosum var. lactucum	KNApSAcK Database	22123792
Stemphylium globuliferum	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.37	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.83 m³·mol⁻¹	ChemAxon
Polarizability	32.62 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002791

Chemspider ID

80909

KEGG Compound ID

C10296

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44139611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Debbab, A., et al. (2009). Debbab, A., et al, J. Nat. Prod. 72, 626 (2009). J. Nat. Prod..

Showing NP-Card for altersolanol A (NP0034377)

MOL for NP0034377 (altersolanol A)

3D MOL for NP0034377 (altersolanol A)

3D SDF for NP0034377 (altersolanol A)

3D-SDF for NP0034377 (altersolanol A)

PDB for NP0034377 (altersolanol A)

3D PDB for NP0034377 (altersolanol A)

SMILES for NP0034377 (altersolanol A)

INCHI for NP0034377 (altersolanol A)

Structure for NP0034377 (altersolanol A)

3D Structure for NP0034377 (altersolanol A)