NP-MRD: Showing NP-Card for (3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid (NP0244448)

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Record Information

Version

2.0

Created at

2022-09-07 05:15:03 UTC

Updated at

2022-09-07 05:15:03 UTC

NP-MRD ID

NP0244448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid

Description

Fridamycin A belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. (3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid was first documented in 2019 (PMID: 30939853). Based on a literature review very few articles have been published on Fridamycin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207152D          

 35 38  0  0  1  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  6  0  0  0
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 22 23  1  0  0  0  0
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 17 26  1  0  0  0  0
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 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    6.7655   -2.4679    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294   -1.0574    1.0916 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0126   -0.9236    0.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516    0.2803    1.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1407    0.5348    0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5635    0.8949   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817   -0.2383    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1439   -0.4025    0.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695   -1.5613    1.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.2037    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0264   -2.2525    1.0767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184   -1.0287   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -1.9641    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7623   -1.7632   -0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.6185   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302   -0.4263   -1.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2873    0.4021   -0.8411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6589    0.5514   -1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726    1.5812   -0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754   -0.4685    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3008    0.2417    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7388    1.3913    1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5981   -0.3695    2.6127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651    0.3131   -1.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    1.4700   -2.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106    0.0956   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7598    1.0882   -1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    2.1339   -1.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4677    1.3421    1.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182    1.0016   -0.1919 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5169    0.4400   -1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -0.1364    0.2709 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2941    0.3310    1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628   -2.9077    1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4193   -2.5469   -0.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008   -3.1395    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.8882    2.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921    0.0909    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611    2.4060   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3555    2.7084   -1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -1.8054    1.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878   -2.8533    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5573   -2.4834   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9243   -1.4005   -2.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3898    0.1045   -2.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6973   -0.0222   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4374    0.2807   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8282    1.6182   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    1.5888    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4829   -0.6779    0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9454   -1.4103    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1121    1.6770   -2.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  4  5  1  0
  5  6  2  0
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  8 29  1  0
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 14 12  1  0
 12 13  2  0
 12  9  1  0
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 34  2  1  0
 10  5  1  0
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 14 28  1  0
  1 36  1  0
  1 37  1  0
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  4 40  1  1
 31 56  1  0
 31 57  1  0
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 34 60  1  6
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  6 41  1  0
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 27 55  1  0
 18 46  1  0
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 21 51  1  0
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 25 54  1  0
 16 45  1  0
 15 44  1  0
 11 43  1  0
M  END


  Mrv1652309072207152D          

 35 38  0  0  1  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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 23 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0244448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](C[C@H](O)[C@H]1O)C1=CC=C2C(=O)C3=C(O)C(C[C@](C)(O)CC(O)=O)=CC=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O10/c1-10-20(29)15(26)7-16(35-10)12-5-6-14-19(22(12)31)24(33)13-4-3-11(21(30)18(13)23(14)32)8-25(2,34)9-17(27)28/h3-6,10,15-16,20,26,29-31,34H,7-9H2,1-2H3,(H,27,28)/t10-,15-,16-,20-,25-/m0/s1

> <INCHI_KEY>
LKLNNJGYAYDANM-FNBXQOAGSA-N

> <FORMULA>
C25H26O10

> <MOLECULAR_WEIGHT>
486.473

> <EXACT_MASS>
486.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.77060983466329

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-4-{6-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid

> <JCHEM_LOGP>
2.168110394666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.594046052655669

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.235425683650896

> <JCHEM_PKA_STRONGEST_BASIC>
-2.966233273094166

> <JCHEM_POLAR_SURFACE_AREA>
181.82

> <JCHEM_REFRACTIVITY>
122.25359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-4-{6-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.874   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.206   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   14   29                                                  
CONECT   29   28    8   30                                                  
CONECT   30   29                                                            
CONECT   31    4   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₁₀

Average Mass

486.4730 Da

Monoisotopic Mass

486.15260 Da

IUPAC Name

(3S)-4-{6-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid

Traditional Name

(3S)-4-{6-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](C[C@H](O)[C@H]1O)C1=CC=C2C(=O)C3=C(O)C(C[C@](C)(O)CC(O)=O)=CC=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C25H26O10/c1-10-20(29)15(26)7-16(35-10)12-5-6-14-19(22(12)31)24(33)13-4-3-11(21(30)18(13)23(14)32)8-25(2,34)9-17(27)28/h3-6,10,15-16,20,26,29-31,34H,7-9H2,1-2H3,(H,27,28)/t10-,15-,16-,20-,25-/m0/s1

InChI Key

LKLNNJGYAYDANM-FNBXQOAGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.17	ChemAxon
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.25 m³·mol⁻¹	ChemAxon
Polarizability	49.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133564763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoon SY, Lee SR, Hwang JY, Benndorf R, Beemelmanns C, Chung SJ, Kim KH: Fridamycin A, a Microbial Natural Product, Stimulates Glucose Uptake without Inducing Adipogenesis. Nutrients. 2019 Apr 1;11(4):765. doi: 10.3390/nu11040765. [PubMed:30939853 ]
LOTUS database [Link]

Showing NP-Card for (3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid (NP0244448)

MOL for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

3D MOL for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

3D SDF for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

3D-SDF for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

PDB for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

3D PDB for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

SMILES for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

INCHI for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

Structure for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)

3D Structure for NP0244448 ((3s)-4-{6-[(2s,4s,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl}-3-hydroxy-3-methylbutanoic acid)