NP-MRD: Showing NP-Card for cytosporin E (NP0037366)

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Record Information

Version

2.0

Created at

2021-06-20 20:18:23 UTC

Updated at

2021-06-30 00:09:32 UTC

NP-MRD ID

NP0037366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cytosporin E

Provided By

JEOL Database JEOL Logo

Description

(1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0²,⁶]Tridec-7-en-4-one belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. cytosporin E is found in Eutypella scoparia. cytosporin E was first documented in 2008 (Ciavatta, E. M., et al.). Based on a literature review very few articles have been published on (1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0²,⁶]Tridec-7-en-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122183D          

 57 59  0  0  0  0            999 V2000
    3.5870    1.7197   -2.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    2.5078   -2.7894 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3761    3.3774   -1.5339 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1412    4.2641   -1.3316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1821    3.5147   -1.1436 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1829    2.6221    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.2875    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3366    0.3639    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -0.9468    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -1.5959   -0.2949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6241   -2.3639   -0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -1.9206    2.1621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9730   -2.9406    1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503   -4.1147    2.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2677   -4.7042    2.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657   -5.1149    1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -3.7712    4.1468 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0779   -3.7429    4.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -2.3758    4.5416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2606   -1.3143    3.5711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0128   -0.8835    4.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699   -0.0888    3.5306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5207   -0.3905    3.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    0.7314    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.9222    2.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.6192    2.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    0.9233    2.4810 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7790    1.0566   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    2.3898   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144    1.1038   -3.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    1.8015   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.1374   -3.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5346    2.7449   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    4.0318   -1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    4.9373   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    4.9059   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4278    2.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    3.1291    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9749   -3.9909    3.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -5.6261    3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -4.9270    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -5.3558    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -6.0458    2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -4.7011    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -4.5151    4.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1772    0.3921    4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    1.6073    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 13 12  1  0  0  0  0
  3  2  1  0  0  0  0
 20 22  1  0  0  0  0
  2  1  1  0  0  0  0
 12  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9  8  2  0  0  0  0
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  8 27  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 20 21  1  1  0  0  0
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 12 44  1  1  0  0  0
  8  7  1  0  0  0  0
 14 15  1  1  0  0  0
 20 12  1  0  0  0  0
 14 16  1  0  0  0  0
 22 27  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
 17 14  1  0  0  0  0
  5  4  1  0  0  0  0
 27 26  1  0  0  0  0
 26 24  1  0  0  0  0
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M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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    2.3021    2.5078   -2.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1821    3.5147   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829    2.6221    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.2875    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0184   -0.9468    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -1.5959   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5207   -0.3905    3.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202122183D          

 57 59  0  0  0  0            999 V2000
    3.5870    1.7197   -2.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    2.5078   -2.7894 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3761    3.3774   -1.5339 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1412    4.2641   -1.3316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1821    3.5147   -1.1436 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1829    2.6221    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.2875    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4450    2.3898   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144    1.1038   -3.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    1.8015   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.1374   -3.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5346    2.7449   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    4.0318   -1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    4.9373   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    4.9059   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9858    4.2510   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    2.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    3.1291    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.8452   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -2.2647   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -0.8876   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102   -2.7515   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -2.3715    2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9749   -3.9909    3.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -5.6261    3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -4.9270    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -5.3558    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -6.0458    2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -4.7011    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -4.5151    4.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847   -4.6689    4.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -2.1520    5.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -2.3707    4.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.7053    4.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    0.3921    4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    1.6073    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 13 12  1  0  0  0  0
  3  2  1  0  0  0  0
 20 22  1  0  0  0  0
  2  1  1  0  0  0  0
 12  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9  8  2  0  0  0  0
 10 11  1  0  0  0  0
  8 27  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 20 21  1  1  0  0  0
 20 19  1  0  0  0  0
 12 44  1  1  0  0  0
  8  7  1  0  0  0  0
 14 15  1  1  0  0  0
 20 12  1  0  0  0  0
 14 16  1  0  0  0  0
 22 27  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
 17 14  1  0  0  0  0
  5  4  1  0  0  0  0
 27 26  1  0  0  0  0
 26 24  1  0  0  0  0
 24 23  1  0  0  0  0
 22 23  1  0  0  0  0
 17 19  1  0  0  0  0
 24 25  2  0  0  0  0
 17 51  1  1  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
  7 40  1  0  0  0  0
  6 39  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  0  0  0  0
 18 52  1  0  0  0  0
 21 55  1  0  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 16 50  1  0  0  0  0
 22 56  1  1  0  0  0
 27 57  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0037366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C(\C([H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]2([H])OC(=O)O[C@@]2([H])[C@@]2(O[H])C([H])([H])[C@]([H])(O[H])C(O[C@@]12[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O7/c1-4-5-6-7-8-9-12-13(11-21)16-20(24,10-14(22)19(2,3)27-16)17-15(12)25-18(23)26-17/h8-9,14-17,21-22,24H,4-7,10-11H2,1-3H3/b9-8+/t14-,15+,16-,17+,20+/m0/s1

> <INCHI_KEY>
IMQYAWIJNZPDJB-QKWWGZASSA-N

> <FORMULA>
C20H30O7

> <MOLECULAR_WEIGHT>
382.453

> <EXACT_MASS>
382.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.886530803257166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0^{2,6}]tridec-7-en-4-one

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.618458004333333

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.991695976883587

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.593730108133325

> <JCHEM_PKA_STRONGEST_BASIC>
-2.780230522570789

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
98.30039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0^{2,6}]tridec-7-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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   -0.0114   -1.9206    2.1621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9730   -2.9406    1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2677   -4.7042    2.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657   -5.1149    1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -3.7712    4.1468 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0779   -3.7429    4.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -2.3758    4.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -1.3143    3.5711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0128   -0.8835    4.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699   -0.0888    3.5306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5207   -0.3905    3.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    0.7314    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.9222    2.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.6192    2.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    0.9233    2.4810 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7790    1.0566   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    2.3898   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144    1.1038   -3.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    1.8015   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.1374   -3.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5346    2.7449   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    4.0318   -1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    4.9373   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    4.9059   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4278    2.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    3.1291    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.8452   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -2.2647   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -0.8876   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102   -2.7515   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -2.3715    2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9749   -3.9909    3.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -5.6261    3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -4.9270    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -5.3558    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -6.0458    2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -4.7011    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -4.5151    4.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847   -4.6689    4.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -2.1520    5.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -2.3707    4.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.7053    4.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    0.3921    4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    1.6073    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 13 12  1  0
  3  2  1  0
 20 22  1  0
  2  1  1  0
 12  9  1  0
  9 10  1  0
  9  8  2  0
 10 11  1  0
  8 27  1  0
 17 18  1  0
 13 14  1  0
 20 21  1  1
 20 19  1  0
 12 44  1  1
  8  7  1  0
 14 15  1  1
 20 12  1  0
 14 16  1  0
 22 27  1  0
  7  6  2  0
  6  5  1  0
 17 14  1  0
  5  4  1  0
 27 26  1  0
 26 24  1  0
 24 23  1  0
 22 23  1  0
 17 19  1  0
 24 25  2  0
 17 51  1  1
 19 53  1  0
 19 54  1  0
  7 40  1  0
  6 39  1  0
  5 37  1  0
  5 38  1  0
  4 35  1  0
  4 36  1  0
  3 33  1  0
  3 34  1  0
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 18 52  1  0
 21 55  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 22 56  1  1
 27 57  1  1
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       3.587   1.720  -2.994  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.302   2.508  -2.789  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.376   3.377  -1.534  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.141   4.264  -1.332  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.182   3.515  -1.144  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.183   2.622   0.067  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.318   1.288   0.001  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.337   0.364   1.137  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.018  -0.947   0.995  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.436  -1.596  -0.295  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.624  -2.364  -0.846  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.011  -1.921   2.162  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.973  -2.941   1.871  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.850  -4.115   2.705  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.268  -4.704   2.768  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.066  -5.115   1.989  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.355  -3.771   4.147  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.078  -3.743   4.245  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.838  -2.376   4.542  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.261  -1.314   3.571  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.013  -0.884   4.105  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.170  -0.089   3.531  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.521  -0.391   3.207  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.022   0.731   2.611  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.205   0.922   2.393  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.026   1.619   2.329  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.789   0.923   2.481  0.00  0.00           C+0
HETATM   28  H   UNK     0       3.779   1.057  -2.144  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.445   2.390  -3.108  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.514   1.104  -3.896  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.468   1.802  -2.718  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.123   3.137  -3.668  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.535   2.745  -0.653  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.254   4.032  -1.605  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.041   4.937  -2.192  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.317   4.906  -0.459  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.986   4.251  -1.019  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.428   2.952  -2.051  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.070   3.129   1.021  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.431   0.845  -0.988  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.284  -2.265  -0.111  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.777  -0.888  -1.053  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.110  -2.752  -0.091  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.991  -2.372   2.152  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.975  -3.991   3.205  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.295  -5.626   3.358  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.643  -4.927   1.763  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.326  -5.356   0.993  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.163  -6.046   2.557  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.066  -4.701   1.824  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.708  -4.515   4.870  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.385  -4.669   4.268  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.508  -2.152   5.564  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.932  -2.371   4.544  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.514  -1.705   4.301  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.177   0.392   4.520  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.026   1.607   2.871  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1   31   32                                             
CONECT    3    4    2   33   34                                             
CONECT    4    3    5   35   36                                             
CONECT    5    6    4   37   38                                             
CONECT    6    7    5   39                                                  
CONECT    7    8    6   40                                                  
CONECT    8    9   27    7                                                  
CONECT    9   12   10    8                                                  
CONECT   10    9   11   41   42                                             
CONECT   11   10   43                                                       
CONECT   12   13    9   44   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14   45   46   47                                             
CONECT   16   14   48   49   50                                             
CONECT   17   18   14   19   51                                             
CONECT   18   17   52                                                       
CONECT   19   20   17   53   54                                             
CONECT   20   22   21   19   12                                             
CONECT   21   20   55                                                       
CONECT   22   20   27   23   56                                             
CONECT   23   24   22                                                       
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   27   24                                                       
CONECT   27    8   22   26   57                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   21                                                            
CONECT   56   22                                                            
CONECT   57   27                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
    3.5870    1.7197   -2.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    2.5078   -2.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761    3.3774   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412    4.2641   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1821    3.5147   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829    2.6221    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.2875    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3366    0.3639    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -0.9468    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -1.5959   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -2.3639   -0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -1.9206    2.1621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9730   -2.9406    1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503   -4.1147    2.7049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2677   -4.7042    2.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657   -5.1149    1.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -3.7712    4.1468 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0779   -3.7429    4.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -2.3758    4.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -1.3143    3.5711 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0128   -0.8835    4.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699   -0.0888    3.5306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5207   -0.3905    3.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    0.7314    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.9222    2.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.6192    2.3289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    0.9233    2.4810 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7790    1.0566   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    2.3898   -3.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144    1.1038   -3.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    1.8015   -2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.1374   -3.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5346    2.7449   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    4.0318   -1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    4.9373   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    4.9059   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9858    4.2510   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    2.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    3.1291    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.8452   -0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -2.2647   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -0.8876   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102   -2.7515   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -2.3715    2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9749   -3.9909    3.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -5.6261    3.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -4.9270    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -5.3558    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -6.0458    2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -4.7011    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -4.5151    4.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847   -4.6689    4.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5084   -2.1520    5.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -2.3707    4.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.7053    4.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    0.3921    4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    1.6073    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 13 12  1  0
  3  2  1  0
 20 22  1  0
  2  1  1  0
 12  9  1  0
  9 10  1  0
  9  8  2  0
 10 11  1  0
  8 27  1  0
 17 18  1  0
 13 14  1  0
 20 21  1  1
 20 19  1  0
 12 44  1  1
  8  7  1  0
 14 15  1  1
 20 12  1  0
 14 16  1  0
 22 27  1  0
  7  6  2  0
  6  5  1  0
 17 14  1  0
  5  4  1  0
 27 26  1  0
 26 24  1  0
 24 23  1  0
 22 23  1  0
 17 19  1  0
 24 25  2  0
 17 51  1  1
 19 53  1  0
 19 54  1  0
  7 40  1  0
  6 39  1  0
  5 37  1  0
  5 38  1  0
  4 35  1  0
  4 36  1  0
  3 33  1  0
  3 34  1  0
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 18 52  1  0
 21 55  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 22 56  1  1
 27 57  1  1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₇

Average Mass

382.4530 Da

Monoisotopic Mass

382.19915 Da

IUPAC Name

(1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0^{2,6}]tridec-7-en-4-one

Traditional Name

(1R,2R,6R,9S,12S)-7-[(1E)-hept-1-en-1-yl]-1,12-dihydroxy-8-(hydroxymethyl)-11,11-dimethyl-3,5,10-trioxatricyclo[7.4.0.0^{2,6}]tridec-7-en-4-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C(\C([H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]2([H])OC(=O)O[C@@]2([H])[C@@]2(O[H])C([H])([H])[C@]([H])(O[H])C(O[C@@]12[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H30O7/c1-4-5-6-7-8-9-12-13(11-21)16-20(24,10-14(22)19(2,3)27-16)17-15(12)25-18(23)26-17/h8-9,14-17,21-22,24H,4-7,10-11H2,1-3H3/b9-8+/t14-,15+,16-,17+,20+/m0/s1

InChI Key

IMQYAWIJNZPDJB-QKWWGZASSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Eutypella scoparia	JEOL database	Ciavatta, E. M., et al, Tetrahedron 64, 5365 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Carbonic acid diester
Oxane
Meta-dioxolane
Tertiary alcohol
Secondary alcohol
Carbonic acid derivative
Dialkyl ether
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.36	ALOGPS
logP	1.62	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.3 m³·mol⁻¹	ChemAxon
Polarizability	40.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

27023789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24882704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ciavatta, E. M., et al. (2008). Ciavatta, E. M., et al, Tetrahedron 64, 5365 (2008). Tetrahedron.

Showing NP-Card for cytosporin E (NP0037366)

MOL for NP0037366 (cytosporin E)

3D MOL for NP0037366 (cytosporin E)

3D SDF for NP0037366 (cytosporin E)

3D-SDF for NP0037366 (cytosporin E)

PDB for NP0037366 (cytosporin E)

3D PDB for NP0037366 (cytosporin E)

SMILES for NP0037366 (cytosporin E)

INCHI for NP0037366 (cytosporin E)

Structure for NP0037366 (cytosporin E)

3D Structure for NP0037366 (cytosporin E)