NP-MRD: Showing NP-Card for epoxycladine A (NP0027938)

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Record Information

Version

2.0

Created at

2021-06-19 19:57:29 UTC

Updated at

2021-06-29 23:54:24 UTC

NP-MRD ID

NP0027938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epoxycladine A

Provided By

JEOL Database JEOL Logo

Description

epoxycladine A is found in Cladiella kashmani. epoxycladine A was first documented in 2005 (Chill, L., et al.). Based on a literature review very few articles have been published on (1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(acetyloxy)-13,14-dihydroxy-3,10,14-trimethyl-7-(propan-2-yl)-4,16-dioxatetracyclo[7.6.1.0²,⁸.0³,⁵]Hexadecan-6-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121573D          

 70 73  0  0  0  0            999 V2000
    1.5336   -4.6175    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -3.3886    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -2.9622    1.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -2.8177    2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204   -1.6179    3.1570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1426   -1.4286    4.0929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4301   -1.7759    3.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -0.3912    3.8489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0232    0.0951    5.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503    0.5262    2.6469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4329    0.5233    1.8037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6226    1.8637    1.0696 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4091    0.3328    3.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7877    2.7761    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 38  1  0  0  0  0
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  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    1.5336   -4.6175    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -3.3886    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192121573D          

 70 73  0  0  0  0            999 V2000
    1.5336   -4.6175    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -3.3886    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -2.9622    1.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -2.8177    2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204   -1.6179    3.1570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1426   -1.4286    4.0929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4301   -1.7759    3.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -0.3912    3.8489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0232    0.0951    5.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503    0.5262    2.6469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4329    0.5233    1.8037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6226    1.8637    1.0696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6699    1.8872   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6795    3.2975   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    1.7284    0.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620    0.7815   -1.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7221    0.9595   -2.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3290    0.7737   -2.0760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9058    0.5615   -1.5290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5175   -0.7865   -0.8431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1855   -1.9959   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -0.9491   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356   -1.1290   -2.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -1.2871   -1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -1.1674   -3.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -0.8321    0.6805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2641   -0.5282    0.8510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946    0.1177    1.6166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2385   -0.3790    2.2440 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9955    0.7652    3.0167 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1373    2.0547    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.3328    3.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -5.3134    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -5.1111    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121   -4.3412    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937   -1.8006    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706   -1.7626    5.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    1.0098    5.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.6464    5.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    0.3144    4.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386    1.5328    3.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    0.3045    2.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062    2.6014    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    2.2195    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745    4.0555    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800    3.4097   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    3.5372   -1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5757    1.5634   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.2066   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396    0.1999   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229    1.7201   -2.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.0249   -2.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151    1.4085   -0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528    0.6898   -2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2607   -2.0390   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -2.9337   -1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -1.9734   -2.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -2.1997   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -1.3623   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -0.4141   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613   -1.8646    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    0.9998    1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905   -0.6732    1.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390    1.0162    3.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    1.8491    1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    2.7761    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    2.5548    2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832   -0.0365    2.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -0.4481    4.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9606    1.1733    3.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 62  1  6  0  0  0
 20 22  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 10 41  1  1  0  0  0
 16 18  1  0  0  0  0
  8  7  1  0  0  0  0
  6  8  1  0  0  0  0
 30 31  1  0  0  0  0
  5 29  1  0  0  0  0
 30 32  1  0  0  0  0
 29 28  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  0  0  0  0
 26 61  1  1  0  0  0
 10 28  1  0  0  0  0
 11 42  1  1  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
  6  7  1  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
 20 26  1  0  0  0  0
 13 15  1  1  0  0  0
 28 26  1  0  0  0  0
 16 17  1  0  0  0  0
 26 27  1  0  0  0  0
 22 23  1  0  0  0  0
 27 11  1  0  0  0  0
 23 25  2  0  0  0  0
 11 10  1  0  0  0  0
 23 24  1  0  0  0  0
 11 12  1  0  0  0  0
  4  2  1  0  0  0  0
 29 30  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
  2  3  2  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 16 49  1  1  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
  6 37  1  1  0  0  0
  5 36  1  1  0  0  0
 29 63  1  6  0  0  0
 30 64  1  1  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 32 68  1  0  0  0  0
 32 69  1  0  0  0  0
 32 70  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 21 57  1  0  0  0  0
 15 48  1  0  0  0  0
 17 50  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027938

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O8/c1-11(2)16-17-18(24(7)21(32-24)19(16)29-12(3)25)14-10-22(5,28)15(27)8-9-23(6,20(17)30-14)31-13(4)26/h11,14-21,27-28H,8-10H2,1-7H3/t14-,15+,16-,17-,18-,19+,20-,21+,22+,23-,24-/m1/s1

> <INCHI_KEY>
VOALFGMUEOTIDZ-WLSPUAMKSA-N

> <FORMULA>
C24H38O8

> <MOLECULAR_WEIGHT>
454.56

> <EXACT_MASS>
454.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.861780225618794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(acetyloxy)-13,14-dihydroxy-3,10,14-trimethyl-7-(propan-2-yl)-4,16-dioxatetracyclo[7.6.1.0^{2,8}.0^{3,5}]hexadecan-6-yl acetate

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
0.8672664730000001

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.079033218515427

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.691343723219266

> <JCHEM_PKA_STRONGEST_BASIC>
-3.234910713209066

> <JCHEM_POLAR_SURFACE_AREA>
114.82000000000001

> <JCHEM_REFRACTIVITY>
113.15320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(acetyloxy)-13,14-dihydroxy-7-isopropyl-3,10,14-trimethyl-4,16-dioxatetracyclo[7.6.1.0^{2,8}.0^{3,5}]hexadecan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    1.5336   -4.6175    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -3.3886    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -2.9622    1.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -2.8177    2.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204   -1.6179    3.1570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1426   -1.4286    4.0929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4301   -1.7759    3.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281   -0.3912    3.8489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0232    0.0951    5.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503    0.5262    2.6469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4329    0.5233    1.8037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6226    1.8637    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699    1.8872   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6795    3.2975   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    1.7284    0.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620    0.7815   -1.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7221    0.9595   -2.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3290    0.7737   -2.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.5615   -1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175   -0.7865   -0.8431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1855   -1.9959   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -0.9491   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356   -1.1290   -2.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -1.2871   -1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -1.1674   -3.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -0.8321    0.6805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2641   -0.5282    0.8510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946    0.1177    1.6166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2385   -0.3790    2.2440 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9955    0.7652    3.0167 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1373    2.0547    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.3328    3.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -5.3134    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -5.1111    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121   -4.3412    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937   -1.8006    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706   -1.7626    5.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    1.0098    5.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0540   -0.6464    5.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    0.3144    4.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386    1.5328    3.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    0.3045    2.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062    2.6014    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    2.2195    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745    4.0555    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800    3.4097   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    3.5372   -1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5757    1.5634   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.2066   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396    0.1999   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229    1.7201   -2.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.0249   -2.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151    1.4085   -0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528    0.6898   -2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2607   -2.0390   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -2.9337   -1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -1.9734   -2.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -2.1997   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -1.3623   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -0.4141   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613   -1.8646    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    0.9998    1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905   -0.6732    1.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390    1.0162    3.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    1.8491    1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    2.7761    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    2.5548    2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832   -0.0365    2.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -0.4481    4.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9606    1.1733    3.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 62  1  6
 20 22  1  1
 12 13  1  0
 13 14  1  0
 13 16  1  0
 10 41  1  1
 16 18  1  0
  8  7  1  0
  6  8  1  0
 30 31  1  0
  5 29  1  0
 30 32  1  0
 29 28  1  0
  8  9  1  1
 10  8  1  0
 26 61  1  1
 10 28  1  0
 11 42  1  1
 18 19  1  0
 20 21  1  0
  6  7  1  0
 19 20  1  0
  5  4  1  0
 20 26  1  0
 13 15  1  1
 28 26  1  0
 16 17  1  0
 26 27  1  0
 22 23  1  0
 27 11  1  0
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 11 10  1  0
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 29 30  1  0
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 17 50  1  0
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 24 60  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.534  -4.617   1.078  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.916  -3.389   1.844  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.057  -2.962   1.941  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.809  -2.818   2.387  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.020  -1.618   3.157  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.143  -1.429   4.093  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.430  -1.776   3.554  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.228  -0.391   3.849  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.023   0.095   5.023  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.150   0.526   2.647  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.433   0.523   1.804  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.623   1.864   1.070  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.670   1.887  -0.059  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.680   3.297  -0.678  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.959   1.728   0.570  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.562   0.782  -1.158  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.722   0.960  -2.018  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.329   0.774  -2.076  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.906   0.562  -1.529  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.518  -0.787  -0.843  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.186  -1.996  -1.527  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.938  -0.949  -0.860  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.636  -1.129  -2.010  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.092  -1.287  -1.692  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.172  -1.167  -3.139  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.877  -0.832   0.681  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.264  -0.528   0.851  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.095   0.118   1.617  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.238  -0.379   2.244  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.996   0.765   3.017  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.137   2.055   2.193  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.409   0.333   3.442  0.00  0.00           C+0
HETATM   33  H   UNK     0       1.002  -5.313   1.732  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.438  -5.111   0.711  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.912  -4.341   0.223  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.894  -1.801   3.789  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.071  -1.763   5.100  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.578   1.010   5.427  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.054  -0.646   5.828  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.056   0.314   4.734  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.939   1.533   3.029  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.329   0.305   2.393  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.906   2.601   1.834  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.671   2.220   0.669  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.874   4.056   0.090  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.480   3.410  -1.418  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.726   3.537  -1.158  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.576   1.563  -0.173  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.739  -0.207  -0.731  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.740   0.200  -2.628  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.323   1.720  -2.635  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.502   0.025  -2.861  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.615   1.409  -0.906  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.253   0.690  -2.402  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.261  -2.039  -1.328  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.737  -2.934  -1.180  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.058  -1.973  -2.613  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.246  -2.200  -1.111  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.660  -1.362  -2.624  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.448  -0.414  -1.139  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.761  -1.865   1.012  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.145   1.000   1.019  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.891  -0.673   1.414  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.439   1.016   3.928  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.567   1.849   1.207  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.788   2.776   2.700  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.174   2.555   2.058  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.983  -0.037   2.585  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.389  -0.448   4.206  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.961   1.173   3.878  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   29    4    6   36                                             
CONECT    6    8    7    5   37                                             
CONECT    7    8    6                                                       
CONECT    8    7    6    9   10                                             
CONECT    9    8   38   39   40                                             
CONECT   10   41    8   28   11                                             
CONECT   11   42   27   10   12                                             
CONECT   12   13   11   43   44                                             
CONECT   13   12   14   16   15                                             
CONECT   14   13   45   46   47                                             
CONECT   15   13   48                                                       
CONECT   16   13   18   17   49                                             
CONECT   17   16   50                                                       
CONECT   18   16   19   51   52                                             
CONECT   19   18   20   53   54                                             
CONECT   20   22   21   19   26                                             
CONECT   21   20   55   56   57                                             
CONECT   22   20   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23   58   59   60                                             
CONECT   25   23                                                            
CONECT   26   61   20   28   27                                             
CONECT   27   26   11                                                       
CONECT   28   62   29   10   26                                             
CONECT   29    5   28   30   63                                             
CONECT   30   31   32   29   64                                             
CONECT   31   30   65   66   67                                             
CONECT   32   30   68   69   70                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   26                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   32                                                            
CONECT   69   32                                                            
CONECT   70   32                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
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    1.9155   -3.3886    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1503    0.5262    2.6469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4329    0.5233    1.8037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6226    1.8637    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699    1.8872   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.9594    1.7284    0.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9378   -0.9491   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356   -1.1290   -2.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -1.2871   -1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1373    2.0547    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4390    1.0162    3.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    1.8491    1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877    2.7761    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3890   -0.4481    4.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9606    1.1733    3.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 62  1  6
 20 22  1  1
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 29 28  1  0
  8  9  1  1
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 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
  6 37  1  1
  5 36  1  1
 29 63  1  6
 30 64  1  1
 14 45  1  0
 14 46  1  0
 14 47  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 32 69  1  0
 32 70  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 15 48  1  0
 17 50  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(Acetyloxy)-13,14-dihydroxy-3,10,14-trimethyl-7-(propan-2-yl)-4,16-dioxatetracyclo[7.6.1.0,.0,]hexadecan-6-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₈O₈

Average Mass

454.5600 Da

Monoisotopic Mass

454.25667 Da

IUPAC Name

(1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(acetyloxy)-13,14-dihydroxy-3,10,14-trimethyl-7-(propan-2-yl)-4,16-dioxatetracyclo[7.6.1.0^{2,8}.0^{3,5}]hexadecan-6-yl acetate

Traditional Name

(1R,2S,3R,5S,6S,7R,8R,9R,10R,13S,14S)-10-(acetyloxy)-13,14-dihydroxy-7-isopropyl-3,10,14-trimethyl-4,16-dioxatetracyclo[7.6.1.0^{2,8}.0^{3,5}]hexadecan-6-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@](OC(=O)C([H])([H])[H])(C([H])([H])[H])[C@]2([H])O[C@]([H])(C([H])([H])[C@@]1(O[H])C([H])([H])[H])[C@]1([H])[C@@]2([H])[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2([H])O[C@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C24H38O8/c1-11(2)16-17-18(24(7)21(32-24)19(16)29-12(3)25)14-10-22(5,28)15(27)8-9-23(6,20(17)30-14)31-13(4)26/h11,14-21,27-28H,8-10H2,1-7H3/t14-,15+,16-,17-,18-,19+,20-,21+,22+,23-,24-/m1/s1

InChI Key

VOALFGMUEOTIDZ-WLSPUAMKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, 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
Cladiella kashmani	JEOL database	Chill, L., et al, J. Nat. Prod. 68, 19 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Oxepane
Dicarboxylic acid or derivatives
Tertiary alcohol
Tetrahydrofuran
1,2-diol
Secondary alcohol
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.82	ALOGPS
logP	0.87	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.15 m³·mol⁻¹	ChemAxon
Polarizability	47.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9399862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11224809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chill, L., et al. (2005). Chill, L., et al, J. Nat. Prod. 68, 19 (2005). J. Nat. Prod..

Showing NP-Card for epoxycladine A (NP0027938)

MOL for NP0027938 (epoxycladine A)

3D MOL for NP0027938 (epoxycladine A)

3D SDF for NP0027938 (epoxycladine A)

3D-SDF for NP0027938 (epoxycladine A)

PDB for NP0027938 (epoxycladine A)

3D PDB for NP0027938 (epoxycladine A)

SMILES for NP0027938 (epoxycladine A)

INCHI for NP0027938 (epoxycladine A)

Structure for NP0027938 (epoxycladine A)

3D Structure for NP0027938 (epoxycladine A)