NP-MRD: Showing NP-Card for (3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0200046)

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Record Information

Version

2.0

Created at

2022-09-04 18:48:45 UTC

Updated at

2022-09-04 18:48:45 UTC

NP-MRD ID

NP0200046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione

Description

Monocillin II glycoside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione is found in Pochonia chlamydosporia. (3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione was first documented in 2003 (PMID: 12828470). Based on a literature review very few articles have been published on Monocillin II glycoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220482D          

 32 34  0  0  1  0            999 V2000
    6.6647    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629    0.6623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6555    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8537   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6463   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758   -2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795   -1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9711   -1.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.8775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -0.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931   -0.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905    0.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    0.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -5.4057    2.3783   -0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381    1.7905   -0.8122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1658    0.5264   -1.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183   -0.7352   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257   -1.3480   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235   -2.5881    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -2.3829    1.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -0.9783    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421    0.1609    2.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799    1.5601    2.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5752    2.1168    3.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606    2.4333    1.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3194    1.8876   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    1.1799    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    0.5904   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.1223   -0.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879   -0.3789    0.7428 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4115   -1.7576    0.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6907   -2.2184    0.8207 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8141   -3.4847    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3728   -3.3280   -1.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641   -1.1133    0.2806 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5770   -1.1294   -1.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153    0.1066    0.8227 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0468    1.2363    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    0.7192   -2.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142    1.4338   -2.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    1.4714   -3.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552    2.0262   -1.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    2.7545   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314    3.5309   -2.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185    2.7861   -1.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6424    3.2169   -1.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    1.6379   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5086    2.7682    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6441    1.5232    0.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572    0.5267   -2.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2286    0.5294   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.1538   -0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -0.9456   -0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -3.4972    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657   -2.8164    1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.8387    2.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -3.0431    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -1.0895    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    0.2809    2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935    3.1017    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2665    3.1740    1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016    1.0636    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.0360    1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -2.4612    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948   -4.2730    0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8497   -3.8313   -0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9133   -3.8779   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5992   -1.1558    0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7553   -0.2331   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1322    0.2331    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    1.8320    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    0.2640   -2.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720    1.9046   -4.0250 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
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 10 11  2  0
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 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 15 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32  2  1  0
 29 13  1  0
 24 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 17 50  1  1
 19 51  1  1
 20 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  1
 23 56  1  0
 24 57  1  1
 25 58  1  0
 26 59  1  0
 28 60  1  0
M  END


  Mrv1652309042220482D          

 32 34  0  0  1  0            999 V2000
    6.6647    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629    0.6623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6555    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8537   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6463   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758   -2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795   -1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9711   -1.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953   -2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.8775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -0.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931   -0.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905    0.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    0.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 17 18  1  0  0  0  0
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  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\CC\C=C\C(=O)CC2=CC(OC3OC(CO)C(O)C3O)=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O9/c1-13-7-5-3-2-4-6-8-15(25)9-14-10-16(11-17(26)19(14)22(29)30-13)31-23-21(28)20(27)18(12-24)32-23/h3,5-6,8,10-11,13,18,20-21,23-24,26-28H,2,4,7,9,12H2,1H3/b5-3+,8-6+/t13-,18?,20?,21?,23?/m0/s1

> <INCHI_KEY>
CNLXHVSPNBJADX-IYXVUPLVSA-N

> <FORMULA>
C23H28O9

> <MOLECULAR_WEIGHT>
448.468

> <EXACT_MASS>
448.173332482

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.07049573365765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecine-1,11-dione

> <JCHEM_LOGP>
2.651555943999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.264581356930913

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.490792750988804

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811523889335785

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
115.61469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3H-2-benzoxacyclotetradecine-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      12.441   2.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.811   1.236   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.290   0.809   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.660  -0.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.140  -1.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.510  -2.608   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.400  -3.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.920  -3.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.811  -4.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.331  -3.889   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.221  -4.957   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.961  -2.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.482  -1.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.372  -3.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.892  -2.608   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.783  -3.676   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.303  -3.248   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.088  -4.194   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.813  -3.331   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.365  -3.855   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.095  -5.371   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.240  -1.851   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.294  -0.636   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.779  -1.800   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.642  -0.525   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.522  -1.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.632  -0.045   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.262   1.450   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.112  -0.472   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.221   0.596   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.852   2.091   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.701   0.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   15   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   13   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    2                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₉

Average Mass

448.4680 Da

Monoisotopic Mass

448.17333 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C\CC\C=C\C(=O)CC2=CC(OC3OC(CO)C(O)C3O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C23H28O9/c1-13-7-5-3-2-4-6-8-15(25)9-14-10-16(11-17(26)19(14)22(29)30-13)31-23-21(28)20(27)18(12-24)32-23/h3,5-6,8,10-11,13,18,20-21,23-24,26-28H,2,4,7,9,12H2,1H3/b5-3+,8-6+/t13-,18?,20?,21?,23?/m0/s1

InChI Key

CNLXHVSPNBJADX-IYXVUPLVSA-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

Species Name	Source	Reference
Pochonia chlamydosporia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Macrolide
O-glycosyl compound
Pentose monosaccharide
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxolane
Vinylogous acid
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Aldehyde
Organic oxide
Carbonyl group
Hydrocarbon derivative
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

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

4979983

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6478917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hellwig V, Mayer-Bartschmid A, Muller H, Greif G, Kleymann G, Zitzmann W, Tichy HV, Stadler M: Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata. J Nat Prod. 2003 Jun;66(6):829-37. doi: 10.1021/np020556v. [PubMed:12828470 ]
LOTUS database [Link]

Showing NP-Card for (3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0200046)

MOL for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D MOL for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D SDF for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D-SDF for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

PDB for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D PDB for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

SMILES for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

INCHI for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

Structure for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D Structure for NP0200046 ((3s,5e,9e)-14-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)