NP-MRD: Showing NP-Card for Ascospiroketal B (NP0006823)

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Record Information

Version

2.0

Created at

2020-12-09 03:44:58 UTC

Updated at

2021-07-15 16:55:53 UTC

NP-MRD ID

NP0006823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ascospiroketal B

Provided By

NPAtlas

Description

Ascospiroketal B is found in Ascochyta. Ascospiroketal B was first documented in 2016 (PMID: 27043130). Based on a literature review very few articles have been published on (4Z,6E)-7-[(2R,3aS,5'R,6S,6aS)-6-(hydroxymethyl)-6-methyl-5-oxo-tetrahydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl 3-hydroxy-2-methylbutanoate (PMID: 29389118).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 65 67  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118353D          

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    5.2776    1.8423    0.0511 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    1.3583   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3933    1.9904   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143   -0.0203   -1.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3223    0.0202   -2.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2400   -0.9059   -1.1578 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8009   -2.1807   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737   -0.4758   -0.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9240   -0.9722   -0.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3944   -0.4904    3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -2.8767    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -2.1110   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4858   -2.8756   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905   -1.0018   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558    0.1226   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    1.4761   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563    1.0414    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816    0.7336    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    1.0011   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522   -0.2992   -3.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046   -0.7289   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8898   -0.5322   -1.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889   -0.9197   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9685   -2.4352   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -1.1961    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203    1.2028   -3.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6478    3.3109   -2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    2.3560   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003    2.5073   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4269    0.2965   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7479   -2.0148   -2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3325   -1.7569   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2510   -1.2916   -3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4205    0.5858   -0.3909 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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 23  1  1  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 23  8  1  0  0  0  0
 22 11  1  0  0  0  0
 21 13  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  6  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  1  0  0  0
  9 43  1  0  0  0  0
  9 44  1  0  0  0  0
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 13 49  1  1  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 20 55  1  0  0  0  0
 21 56  1  1  0  0  0
 27 57  1  6  0  0  0
 28 58  1  0  0  0  0
 28 59  1  0  0  0  0
 28 60  1  0  0  0  0
 29 61  1  6  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 31 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(C(=O)O[C@@]2([H])C([H])([H])[C@]3(O[C@@]([H])(C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])[C@]([H])(OC(=O)[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C3([H])[H])O[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O8/c1-14(28-20(26)15(2)16(3)25)8-6-5-7-9-17-10-11-23(30-17)12-18-19(31-23)22(4,13-24)21(27)29-18/h5-7,9,14-19,24-25H,8,10-13H2,1-4H3/b6-5-,9-7+/t14-,15-,16-,17+,18+,19-,22+,23-/m1/s1

> <INCHI_KEY>
NQHCVEOIXCDKGY-VMWMRIIOSA-N

> <FORMULA>
C23H34O8

> <MOLECULAR_WEIGHT>
438.517

> <EXACT_MASS>
438.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.53525834046907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4Z,6E)-7-[(2R,3aS,5'R,6S,6aS)-6-(hydroxymethyl)-6-methyl-5-oxo-tetrahydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl (2R,3R)-3-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.490545904333332

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.229283512946992

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.597622138980867

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867798203078022

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000002

> <JCHEM_REFRACTIVITY>
113.13000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4Z,6E)-7-[(2R,3aS,5'R,6S,6aS)-6-(hydroxymethyl)-6-methyl-5-oxo-dihydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl (2R,3R)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -3.2296   -0.9339    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232    0.4621    0.5894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8916    1.4332    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483    1.4698    2.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529    0.8247    2.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -0.2066    1.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -0.8091    2.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -1.8759    1.4684 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9756   -1.9868    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.7631   -0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -0.6317    0.2326 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1737    0.7666    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    0.7532    0.7592 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2776    1.8423    0.0511 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    1.3583   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3933    1.9904   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143   -0.0203   -1.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3223    0.0202   -2.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2400   -0.9059   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8009   -2.1807   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737   -0.4758   -0.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9240   -0.9722   -0.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -1.5395    1.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609    0.7043   -0.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061    0.8988   -1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0707    0.8599   -2.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0579    2.4191   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4707    0.0403   -2.0564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9354   -1.3148   -2.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306    0.0618   -0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3155   -1.2198    1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9489    2.5131    1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1445    1.1145    3.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874   -0.5528    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.4904    3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -2.8767    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -2.1110   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4858   -2.8756   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905   -1.0018   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7563    1.0414    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816    0.7336    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    1.0011   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522   -0.2992   -3.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046   -0.7289   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8898   -0.5322   -1.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889   -0.9197   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6478    3.3109   -2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    2.3560   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003    2.5073   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4269    0.2965   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7479   -2.0148   -2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3325   -1.7569   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2510   -1.2916   -3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4205    0.5858   -0.3909 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 11 23  1  1
  2 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 23  8  1  0
 22 11  1  0
 21 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  1
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  9 44  1  0
 10 45  1  0
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 12 47  1  0
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 18 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
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 20 55  1  0
 21 56  1  1
 27 57  1  6
 28 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  6
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  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      -3.230  -0.934   1.127  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.023   0.462   0.589  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.892   1.433   1.657  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.848   1.470   2.629  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.753   0.825   2.811  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.269  -0.207   1.956  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.885  -0.809   2.280  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.462  -1.876   1.468  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.976  -1.987   0.072  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.589  -0.763  -0.574  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.866  -0.632   0.233  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.174   0.767   0.648  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.680   0.753   0.759  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.278   1.842   0.051  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.348   1.358  -0.674  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.393   1.990  -0.922  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.014  -0.020  -1.083  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.322   0.020  -2.421  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.240  -0.906  -1.158  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.801  -2.181  -1.554  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.074  -0.476  -0.007  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.924  -0.972  -0.608  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.821  -1.540   1.259  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.261   0.704  -0.173  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.206   0.899  -1.533  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.071   0.860  -2.078  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.450   1.149  -2.347  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.058   2.419  -1.789  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.471   0.040  -2.056  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.935  -1.315  -2.410  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.631   0.062  -0.651  0.00  0.00           O+0
HETATM   32  H   UNK     0      -2.685  -1.718   0.581  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.019  -0.904   2.223  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.316  -1.220   1.069  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.197   0.486  -0.146  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.878   1.476   2.285  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.949   2.513   1.186  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.990   2.264   3.471  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.145   1.115   3.725  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.687  -0.553   1.063  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.394  -0.490   3.168  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.417  -2.877   1.949  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.089  -2.111  -0.086  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.486  -2.876  -0.382  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.791  -1.002  -1.636  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.956   0.123  -0.548  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.821   1.476  -0.102  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.756   1.041   1.635  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.982   0.734   1.813  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.869   1.001  -2.641  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.052  -0.299  -3.195  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.505  -0.729  -2.426  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.890  -0.532  -1.979  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.789  -0.920  -0.212  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.968  -2.435  -1.081  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.525  -1.196   0.703  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.220   1.203  -3.410  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.648   3.311  -2.342  0.00  0.00           H+0
HETATM   59  H   UNK     0      -7.147   2.356  -1.843  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.800   2.507  -0.699  0.00  0.00           H+0
HETATM   61  H   UNK     0      -7.427   0.297  -2.508  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.748  -2.015  -2.679  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.332  -1.757  -1.579  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.251  -1.292  -3.287  0.00  0.00           H+0
HETATM   65  H   UNK     0      -7.420   0.586  -0.391  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   24   35                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   38                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5    7   40                                                  
CONECT    7    6    8   41                                                  
CONECT    8    7    9   23   42                                             
CONECT    9    8   10   43   44                                             
CONECT   10    9   11   45   46                                             
CONECT   11   10   12   23   22                                             
CONECT   12   11   13   47   48                                             
CONECT   13   12   14   21   49                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   21                                             
CONECT   18   17   50   51   52                                             
CONECT   19   17   20   53   54                                             
CONECT   20   19   55                                                       
CONECT   21   17   22   13   56                                             
CONECT   22   21   11                                                       
CONECT   23   11    8                                                       
CONECT   24    2   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   57                                             
CONECT   28   27   58   59   60                                             
CONECT   29   27   30   31   61                                             
CONECT   30   29   62   63   64                                             
CONECT   31   29   65                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  134    0
END

RDKit          3D

65 67  0  0  0  0  0  0  0  0999 V2000
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   -3.0232    0.4621    0.5894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8916    1.4332    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483    1.4698    2.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2690   -0.2066    1.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -0.8091    2.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -1.8759    1.4684 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9756   -1.9868    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.7631   -0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -0.6317    0.2326 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1737    0.7666    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    0.7532    0.7592 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2776    1.8423    0.0511 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    1.3583   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3933    1.9904   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143   -0.0203   -1.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3223    0.0202   -2.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2400   -0.9059   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8009   -2.1807   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9240   -0.9722   -0.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2609    0.7043   -0.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061    0.8988   -1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0707    0.8599   -2.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496    1.1492   -2.3467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0579    2.4191   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4707    0.0403   -2.0564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9354   -1.3148   -2.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306    0.0618   -0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -1.7185    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193   -0.9035    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3155   -1.2198    1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1974    0.4855   -0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8780    1.4759    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    2.5131    1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    2.2638    3.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    1.1145    3.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874   -0.5528    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.4904    3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -2.8767    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -2.1110   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4858   -2.8756   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905   -1.0018   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558    0.1226   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    1.4761   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563    1.0414    1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816    0.7336    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    1.0011   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522   -0.2992   -3.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046   -0.7289   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8898   -0.5322   -1.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889   -0.9197   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9685   -2.4352   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -1.1961    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203    1.2028   -3.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6478    3.3109   -2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    2.3560   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003    2.5073   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4269    0.2965   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7479   -2.0148   -2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3325   -1.7569   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2510   -1.2916   -3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4205    0.5858   -0.3909 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 11 23  1  1
  2 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 23  8  1  0
 22 11  1  0
 21 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  1
  9 43  1  0
  9 44  1  0
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 18 50  1  0
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 27 57  1  6
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 28 60  1  0
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 30 63  1  0
 30 64  1  0
 31 65  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4Z,6E)-7-[(2R,3AS,5'r,6S,6as)-6-(hydroxymethyl)-6-methyl-5-oxo-tetrahydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl 3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₂₃H₃₄O₈

Average Mass

438.5170 Da

Monoisotopic Mass

438.22537 Da

IUPAC Name

(2R,4Z,6E)-7-[(2R,3aS,5'R,6S,6aS)-6-(hydroxymethyl)-6-methyl-5-oxo-tetrahydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl (2R,3R)-3-hydroxy-2-methylbutanoate

Traditional Name

(2R,4Z,6E)-7-[(2R,3aS,5'R,6S,6aS)-6-(hydroxymethyl)-6-methyl-5-oxo-dihydro-3H-spiro[furo[3,2-b]furan-2,2'-oxolane]-5'-yl]hepta-4,6-dien-2-yl (2R,3R)-3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C\C=C/C=C/[C@H]1CC[C@@]2(C[C@@H]3OC(=O)[C@@](C)(CO)[C@@H]3O2)O1)OC(=O)C(C)C(C)O

InChI Identifier

InChI=1S/C23H34O8/c1-14(28-20(26)15(2)16(3)25)8-6-5-7-9-17-10-11-23(30-17)12-18-19(31-23)22(4,13-24)21(27)29-18/h5-7,9,14-19,24-25H,8,10-13H2,1-4H3/b6-5-,9-7+/t14?,15?,16?,17-,18-,19+,22-,23+/m0/s1

InChI Key

NQHCVEOIXCDKGY-VMWMRIIOSA-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
Ascochyta	NPAtlas	17217274

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	2.78	ALOGPS
logP	2.49	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	113.13 m³·mol⁻¹	ChemAxon
Polarizability	46.54 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

NPAtlas ID

NPA007640

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17214419

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833223

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hara Y, Honda T, Arakawa K, Ota K, Kamaike K, Miyaoka H: Total Synthesis of ent-Ascospiroketal B. J Org Chem. 2018 Feb 16;83(4):1976-1987. doi: 10.1021/acs.joc.7b02925. Epub 2018 Feb 8. [PubMed:29389118 ]
Wang J, Tong R: Asymmetric Total Syntheses of ent-Ascospiroketals A and B. Org Lett. 2016 Apr 15;18(8):1936-9. doi: 10.1021/acs.orglett.6b00796. Epub 2016 Apr 4. [PubMed:27043130 ]

Showing NP-Card for Ascospiroketal B (NP0006823)

MOL for NP0006823 (Ascospiroketal B)

3D MOL for NP0006823 (Ascospiroketal B)

3D SDF for NP0006823 (Ascospiroketal B)

3D-SDF for NP0006823 (Ascospiroketal B)

PDB for NP0006823 (Ascospiroketal B)

3D PDB for NP0006823 (Ascospiroketal B)

SMILES for NP0006823 (Ascospiroketal B)

INCHI for NP0006823 (Ascospiroketal B)

Structure for NP0006823 (Ascospiroketal B)

3D Structure for NP0006823 (Ascospiroketal B)