NP-MRD: Showing NP-Card for Anhydroexfoliamycin (NP0022953)

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Record Information

Version

1.0

Created at

2021-01-06 08:05:58 UTC

Updated at

2021-07-15 17:40:26 UTC

NP-MRD ID

NP0022953

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anhydroexfoliamycin

Provided By

NPAtlas

Description

Anhydroexfoliamycin is found in Streptomyces exfoliatus. It was first documented in 1993 (PMID: 8468251). Based on a literature review very few articles have been published on (1R)-8-[(2R,3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione (PMID: 34383398) (PMID: 34383397) (PMID: 34383396) (PMID: 34384147) (PMID: 34384146) (PMID: 34384145).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105383D          

 54 57  0  0  0  0            999 V2000
   -6.1279    1.4804    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    2.1730    1.6084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7604    1.6325    0.6751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5105    0.1565    1.0072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7056   -0.5424    0.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917   -1.4792   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3678   -2.0600   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957   -1.8404   -0.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6093   -1.7391   -1.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9138    1.0506    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888   -0.3660    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    0.1665   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4105   -0.2941   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241    0.2735   -0.9287 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1475    0.2694    0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326    1.0213    0.2495 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1266    1.0705    1.5353 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1259   -1.1931   -2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -1.7136   -2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639   -2.5743   -3.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3348    1.0765    0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9641    2.1661    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3986    2.1128    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0563    1.7408   -0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.1883    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6010   -2.2438   -1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0713   -1.3565    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9488   -1.5302   -2.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15  4  1  0  0  0  0
 26 19  1  0  0  0  0
 15  9  1  0  0  0  0
 29 11  1  0  0  0  0
  1 31  1  0  0  0  0
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  2 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  1  0  0  0
  7 39  1  0  0  0  0
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  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
 10 43  1  0  0  0  0
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M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
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   -4.7950    2.1730    1.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1475    0.2694    0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242105383D          

 54 57  0  0  0  0            999 V2000
   -6.1279    1.4804    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    2.1730    1.6084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7604    1.6325    0.6751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5105    0.1565    1.0072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7056   -0.5424    0.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3678   -2.0600   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6527   -1.2962   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7737   -1.7136   -2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639   -2.5743   -3.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9641    2.1661    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9740    3.2612    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2378    0.1279    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -3.0556    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6010   -2.2438   -1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0713   -1.3565    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2025   -2.5749   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -2.4727   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1409    1.5253    1.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865    1.3904   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.0061   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    1.5896    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4856    0.0741    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0653    2.5534    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7307    0.8808   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1524   -1.4757    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088    0.1764   -2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979   -1.9465   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -1.5302   -2.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 15  4  1  0  0  0  0
 26 19  1  0  0  0  0
 15  9  1  0  0  0  0
 29 11  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  2 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  1  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
 10 43  1  0  0  0  0
 14 44  1  0  0  0  0
 19 45  1  6  0  0  0
 21 46  1  6  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 23 49  1  0  0  0  0
 24 50  1  6  0  0  0
 25 51  1  0  0  0  0
 26 52  1  6  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(C([H])=C(O[C@]2([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])[H])=C([H])C2=C1C(=O)C(=C([H])C2=O)[C@@]1([H])O[C@@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-3-4-14-16-10(5-9(2)29-14)6-11-13(24)7-12(18(25)17(11)20(16)27)22-21(28)19(26)15(8-23)30-22/h5-7,14-15,19,21-23,26-28H,3-4,8H2,1-2H3/t14-,15+,19-,21-,22-/m1/s1

> <INCHI_KEY>
SZBHSSGJBUMHOR-CGMMKJMPSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.426

> <EXACT_MASS>
416.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.77542328212357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-8-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.0622455149999994

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.749216972421044

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.648463105941006

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791991948466165

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
108.96849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-8-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H-cyclohexa[g]isochromene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -6.1279    1.4804    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    2.1730    1.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7604    1.6325    0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5105    0.1565    1.0072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7056   -0.5424    0.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917   -1.4792   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3678   -2.0600   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957   -1.8404   -0.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6527   -1.2962   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6093   -1.7391   -1.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -1.2690   -1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778   -0.3224   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044    0.1407    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9138    1.0506    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888   -0.3660    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    0.1665   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909    1.0180    0.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105   -0.2941   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241    0.2735   -0.9287 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1475    0.2694    0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326    1.0213    0.2495 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1266    1.0705    1.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2716    1.8312    1.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0427    0.2764   -0.8378 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7587   -0.8087   -0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -0.2557   -1.6952 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9609   -1.6501   -1.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.1931   -2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -1.7136   -2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639   -2.5743   -3.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1675    0.6301    2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3348    1.0765    0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9641    2.1661    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3986    2.1128    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9740    3.2612    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0563    1.7408   -0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.1883    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.1279    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -3.0556    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6010   -2.2438   -1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0713   -1.3565    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2025   -2.5749   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -2.4727   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1409    1.5253    1.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865    1.3904   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.0061   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    1.5896    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4856    0.0741    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0653    2.5534    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7307    0.8808   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1524   -1.4757    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088    0.1764   -2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979   -1.9465   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -1.5302   -2.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 18 28  2  0
 28 29  1  0
 29 30  2  0
 15  4  1  0
 26 19  1  0
 15  9  1  0
 29 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  1
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 14 44  1  0
 19 45  1  6
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  6
 25 51  1  0
 26 52  1  6
 27 53  1  0
 28 54  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      -6.128   1.480   1.538  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.795   2.173   1.608  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.760   1.633   0.675  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.510   0.157   1.007  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.706  -0.542   0.852  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.992  -1.479  -0.123  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.368  -2.060  -0.280  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.996  -1.840  -0.912  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.653  -1.296  -0.790  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.609  -1.739  -1.594  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.339  -1.269  -1.442  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.078  -0.322  -0.459  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.104   0.141   0.361  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.914   1.051   1.327  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.389  -0.366   0.171  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.282   0.167  -0.311  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.591   1.018   0.552  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.410  -0.294  -1.158  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.724   0.274  -0.929  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.147   0.269   0.424  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.333   1.021   0.250  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.127   1.071   1.535  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.272   1.831   1.263  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.043   0.276  -0.838  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.759  -0.809  -0.324  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.871  -0.256  -1.695  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.961  -1.650  -1.751  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.126  -1.193  -2.082  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.774  -1.714  -2.267  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.564  -2.574  -3.170  0.00  0.00           O+0
HETATM   31  H   UNK     0      -6.168   0.630   2.228  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.335   1.077   0.506  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.964   2.166   1.833  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.399   2.113   2.662  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.974   3.261   1.434  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.056   1.741  -0.394  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.822   2.188   0.828  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.238   0.128   2.083  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.425  -3.056   0.228  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.601  -2.244  -1.341  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.071  -1.357   0.198  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.202  -2.575  -1.678  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.816  -2.473  -2.354  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.141   1.525   1.634  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.687   1.390  -1.161  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.031   2.006  -0.105  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.562   1.590   2.317  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.486   0.074   1.842  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.065   2.553   0.590  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.731   0.881  -1.425  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.152  -1.476   0.097  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.009   0.176  -2.697  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.898  -1.946  -1.872  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.949  -1.530  -2.718  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34   35                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   15   38                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6   39   40   41                                             
CONECT    8    6    9   42                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   44                                                       
CONECT   15   13    4    9                                                  
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20   26   45                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   24   46                                             
CONECT   22   21   23   47   48                                             
CONECT   23   22   49                                                       
CONECT   24   21   25   26   50                                             
CONECT   25   24   51                                                       
CONECT   26   24   27   19   52                                             
CONECT   27   26   53                                                       
CONECT   28   18   29   54                                                  
CONECT   29   28   30   11                                                  
CONECT   30   29                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43   10                                                            
CONECT   44   14                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
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    4.8713   -0.2557   -1.6952 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9609   -1.6501   -1.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.1931   -2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5639   -2.5743   -3.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9740    3.2612    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0563    1.7408   -0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224    2.1883    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4246   -3.0556    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2025   -2.5749   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -2.4727   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1409    1.5253    1.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865    1.3904   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    2.0061   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    1.5896    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4856    0.0741    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0653    2.5534    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7307    0.8808   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1524   -1.4757    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088    0.1764   -2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979   -1.9465   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -1.5302   -2.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6  7  1  0
  6  8  2  0
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  9 10  2  0
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 26 19  1  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
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  4 38  1  1
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 28 54  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₈

Average Mass

416.4260 Da

Monoisotopic Mass

416.14712 Da

IUPAC Name

(1R)-8-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione

Traditional Name

(1R)-8-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H-cyclohexa[g]isochromene-6,9-dione

CAS Registry Number

Not Available

SMILES

CCC[C@H]1OC(C)=CC2=C1C(O)=C1C(=O)C(=CC(=O)C1=C2)[C@H]1OC(CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H24O8/c1-3-4-14-16-10(5-9(2)29-14)6-11-13(24)7-12(18(25)17(11)20(16)27)22-21(28)19(26)15(8-23)30-22/h5-7,14-15,19,21-23,26-28H,3-4,8H2,1-2H3/t14-,15?,19-,21-,22-/m1/s1

InChI Key

SZBHSSGJBUMHOR-CGMMKJMPSA-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
Streptomyces exfoliatus	NPAtlas	8468251

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	1.58	ALOGPS
logP	1.06	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.97 m³·mol⁻¹	ChemAxon
Polarizability	43.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003942

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436697

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584190

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Potterat O, Zahner H, Volkmann C, Zeeck A: Metabolic products of microorganisms. 264. Exfoliamycin and related metabolites, new naphthoquinone antibiotics from Streptomyces exfoliatus. J Antibiot (Tokyo). 1993 Feb;46(2):346-9. doi: 10.7164/antibiotics.46.346. [PubMed:8468251 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
Authors unspecified: Ponesimod. 2012. [PubMed:34383396 ]
Lee J, Cho Y, Choi KH, Hwang I, Oh YL: Metastatic leiomyosarcoma of the thyroid gland: cytologic findings and differential diagnosis. J Pathol Transl Med. 2021 Aug 13. pii: jptm.2021.06.23. doi: 10.4132/jptm.2021.06.23. [PubMed:34384147 ]
Rossouw HM, Nagel SE, Pillay TS: Comparability of 11 different equations for estimating LDL cholesterol on different analysers. Clin Chem Lab Med. 2021 Aug 11. pii: cclm-2021-0747. doi: 10.1515/cclm-2021-0747. [PubMed:34384146 ]
Winkel P, Hilden J, Jakobsen JC, Lindschou J, Jensen GB, Kjoller E, Sajadieh A, Kastrup J, Kolmos HJ, Larsson A, Arnlov J, Bjerre M, Gluud C: A screening method to spot biomarkers that may warn of serious events in a chronic disease - illustrated by cardiological CLARICOR trial data. Clin Chem Lab Med. 2021 Aug 12. pii: cclm-2021-0333. doi: 10.1515/cclm-2021-0333. [PubMed:34384145 ]
Lombardi Y, Hiesse C, Ridel C, Touzot M: From combined heart-kidney to kidney transplantation program: what nephrologists should know about dilated cardiomyopathy. Transpl Int. 2021 Aug;34(8):1573-1575. doi: 10.1111/tri.13948. [PubMed:34384144 ]
Anderson LL, Heblinski M, Absalom NL, Hawkins NA, Bowen M, Benson MJ, Zhang F, Bahceci D, Doohan PT, Chebib M, McGregor IS, Kearney JA, Arnold JC: Cannabigerolic acid, a major biosynthetic precursor molecule in cannabis, exhibits divergent effects on seizures in mouse models of epilepsy. Br J Pharmacol. 2021 Aug 12. doi: 10.1111/bph.15661. [PubMed:34384142 ]
Kennedy LJ, Cukier S, Khoury L, Steeves D: 'You drink at home so they can go to work safely': A case study exploring alcohol marketing during the COVID-19 pandemic. Drug Alcohol Rev. 2021 Aug 12. doi: 10.1111/dar.13374. [PubMed:34384143 ]
Voerman E, Jaddoe VWV, Shokry E, Ruijter GJG, Felix JF, Koletzko B, Gaillard R: Associations of maternal and infant metabolite profiles with foetal growth and the odds of adverse birth outcomes. Pediatr Obes. 2021 Aug 12:e12844. doi: 10.1111/ijpo.12844. [PubMed:34384140 ]
Milakovic L, Hintermeier P, Liu Y, Barath E, Lercher J: Influence of intracrystalline ionic strength in MFI zeolites on aqueous phase dehydration of methylcyclohexanols. Angew Chem Int Ed Engl. 2021 Aug 12. doi: 10.1002/anie.202107947. [PubMed:34384139 ]
Chou KT, Tsai YL, Yeh WY, Chen YM, Huang N, Cheng HM: Risk of work-related injury in workers with obstructive sleep apnea: A systematic review and meta-analysis. J Sleep Res. 2021 Aug 12:e13446. doi: 10.1111/jsr.13446. [PubMed:34384138 ]
Gegunde S, Alfonso A, Alvarino R, Perez-Fuentes N, Botana LM: Anhydroexfoliamycin, a Streptomyces Secondary Metabolite, Mitigates Microglia-Driven Inflammation. ACS Chem Neurosci. 2021 Jul 7;12(13):2336-2346. doi: 10.1021/acschemneuro.1c00033. Epub 2021 Jun 10. [PubMed:34110771 ]
Kabir MT, Uddin MS, Jeandet P, Emran TB, Mitra S, Albadrani GM, Sayed AA, Abdel-Daim MM, Simal-Gandara J: Anti-Alzheimer's Molecules Derived from Marine Life: Understanding Molecular Mechanisms and Therapeutic Potential. Mar Drugs. 2021 Apr 28;19(5). pii: md19050251. doi: 10.3390/md19050251. [PubMed:33925063 ]
Leiros M, Alonso E, Rateb ME, Ebel R, Jaspars M, Alfonso A, Botana LM: The Streptomyces metabolite anhydroexfoliamycin ameliorates hallmarks of Alzheimer's disease in vitro and in vivo. Neuroscience. 2015 Oct 1;305:26-35. doi: 10.1016/j.neuroscience.2015.07.082. Epub 2015 Aug 3. [PubMed:26247694 ]
Leiros M, Alonso E, Sanchez JA, Rateb ME, Ebel R, Houssen WE, Jaspars M, Alfonso A, Botana LM: Mitigation of ROS insults by Streptomyces secondary metabolites in primary cortical neurons. ACS Chem Neurosci. 2014 Jan 15;5(1):71-80. doi: 10.1021/cn4001878. Epub 2013 Nov 19. [PubMed:24219236 ]

Showing NP-Card for Anhydroexfoliamycin (NP0022953)

MOL for NP0022953 (Anhydroexfoliamycin)

3D MOL for NP0022953 (Anhydroexfoliamycin)

3D SDF for NP0022953 (Anhydroexfoliamycin)

3D-SDF for NP0022953 (Anhydroexfoliamycin)

PDB for NP0022953 (Anhydroexfoliamycin)

3D PDB for NP0022953 (Anhydroexfoliamycin)

SMILES for NP0022953 (Anhydroexfoliamycin)

INCHI for NP0022953 (Anhydroexfoliamycin)

Structure for NP0022953 (Anhydroexfoliamycin)

3D Structure for NP0022953 (Anhydroexfoliamycin)