NP-MRD: Showing NP-Card for (1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate (NP0297245)

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Record Information

Version

2.0

Created at

2022-09-10 07:23:54 UTC

Updated at

2022-09-10 07:23:54 UTC

NP-MRD ID

NP0297245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate

Description

Briaexcavatolide G belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate is found in Briareum excavatum. Based on a literature review very few articles have been published on Briaexcavatolide G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102209232D          

 32 36  0  0  1  0            999 V2000
    0.2137   -1.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -0.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125    0.0207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6505   -0.2930    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7517    1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143    1.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5165    2.2936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    2.1744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1435    2.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.5456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6776    2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2459    1.8593    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1834    2.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    3.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372    3.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772    3.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    1.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3251    2.4416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7910    3.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367    2.5898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141    3.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708    1.9610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2049    1.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    1.1841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5818    1.0359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2349    0.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    0.2132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4460    0.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.4890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1015   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -0.8027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  6  0  0  0
  2 32  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
    2.8257    3.0491    1.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    2.2340    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510    0.8770    0.5169 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6619    1.0302    0.7456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7170   -0.2735   -0.2688 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4469   -0.4543   -1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617   -1.7744   -1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590   -2.4405   -2.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9259   -2.2511   -1.0630 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1158   -2.9499   -2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140   -0.8781   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0228   -0.4686   -2.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987   -0.7556    0.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0351   -1.7791    1.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -1.9512    2.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -3.2092    3.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687   -1.0226    3.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8856    0.0249   -0.2969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9290   -0.8425   -0.9189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0135   -1.3748   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017   -0.0347   -2.0264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6198   -0.7568   -2.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533    1.2501   -1.4206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2286    2.3793   -1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119    1.6961   -0.2208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3866    1.1518    0.4856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8598    0.7803    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    2.3481    0.7254 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2994    2.1093    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212    3.0547   -0.3696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6766    2.4990   -1.4982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    2.9216   -0.6325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5616    4.0925    1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460    2.7384    2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422    0.6178    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.1076    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2662   -2.8621   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -3.7136   -2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -2.2670   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1901   -3.4242   -1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -0.0826   -2.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -0.0032    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2582   -3.4285    2.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662   -3.1035    4.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4648   -4.0592    2.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287    0.5126   -1.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4490   -1.6906   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217   -0.6508    0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631   -1.9821   -0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7344   -2.1148    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595    0.1948   -2.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -1.6690   -2.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058    1.5129   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2197    2.3664    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0906    1.0461    2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964   -0.2618    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7461    1.4033    2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    3.0753    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2324    2.7508    2.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686    4.0911   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386    3.8305   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 32  1  0
 32 31  1  0
 31 30  1  0
 30 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  1
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 19  1  0
 19 20  1  0
 19 18  1  0
 18 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 11  1  0
 11 12  1  6
 11  9  1  0
 11  5  1  0
 30 32  1  0
 18 26  1  0
 23 25  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  9 37  1  1
  5 36  1  1
  3 35  1  1
  1 33  1  0
  1 34  1  0
 32 61  1  6
 30 60  1  6
 28 58  1  1
 29 59  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 25 54  1  1
 23 53  1  1
 21 51  1  6
 22 52  1  0
 19 47  1  6
 20 48  1  0
 20 49  1  0
 20 50  1  0
 18 46  1  6
 13 42  1  1
 16 43  1  0
 16 44  1  0
 16 45  1  0
 12 41  1  0
M  END


  Mrv1652309102209232D          

 32 36  0  0  1  0            999 V2000
    0.2137   -1.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -0.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125    0.0207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6505   -0.2930    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.8434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7517    1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143    1.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5165    2.2936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    2.1744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1435    2.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.5456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6776    2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2459    1.8593    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1834    2.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    3.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372    3.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772    3.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    1.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3251    2.4416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7910    3.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367    2.5898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141    3.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708    1.9610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2049    1.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    1.1841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5818    1.0359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2349    0.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    0.2132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4460    0.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.4890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1015   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -0.8027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  6  0  0  0
  2 32  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@H]3[C@H](O)[C@@]3(C)[C@H]4O[C@H]4[C@H](O)[C@H](C)[C@@H]3[C@@H](OC(C)=O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C22H29ClO9/c1-6-10-17(29-9(4)24)22(28)8(3)20(27)32-18(22)11(23)7(2)13-15(30-13)16(26)21(10,5)19-14(31-19)12(6)25/h6,8,10-19,25-26,28H,2H2,1,3-5H3/t6-,8+,10-,11+,12-,13-,14+,15-,16+,17-,18+,19+,21+,22-/m1/s1

> <INCHI_KEY>
SJZPSOOIOQXIIP-CECLVVHISA-N

> <FORMULA>
C22H29ClO9

> <MOLECULAR_WEIGHT>
472.92

> <EXACT_MASS>
472.1500102

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.37020571388791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,5R,7S,8R,11R,12R,13R,14S,15R,16R,17S,19R)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{8,12}.0^{17,19}]nonadecan-13-yl acetate

> <JCHEM_LOGP>
0.031978814000000175

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.42243883012399

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.333136477428198

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2955408254812575

> <JCHEM_POLAR_SURFACE_AREA>
138.35000000000002

> <JCHEM_REFRACTIVITY>
106.564

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,5R,7S,8R,11R,12R,13R,14S,15R,16R,17S,19R)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{8,12}.0^{17,19}]nonadecan-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.399  -2.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.207  -1.135   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.210   0.039   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -1.214  -0.547   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       0.093   1.574   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.403   1.938   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.520   3.473   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.831   4.281   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.096   4.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.268   5.555   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.901   2.885   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.265   4.382   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.326   3.471   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.209   5.006   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.821   5.673   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.630   6.191   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.704   7.209   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.822   3.107   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.340   4.558   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.343   5.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.855   4.834   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.373   6.285   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.852   3.661   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.849   2.487   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.334   2.210   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.819   1.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.039   0.993   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.936   0.398   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.433   0.035   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.128  -0.913   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.923  -2.439   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.704  -1.498   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   26                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26                                                  
CONECT   26   25   18   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30   32                                                       
CONECT   32   31    2   30                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉ClO₉

Average Mass

472.9200 Da

Monoisotopic Mass

472.15001 Da

IUPAC Name

(1S,2R,3S,5R,7S,8R,11R,12R,13R,14S,15R,16R,17S,19R)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{8,12}.0^{17,19}]nonadecan-13-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@H]3[C@H](O)[C@@]3(C)[C@H]4O[C@H]4[C@H](O)[C@H](C)[C@@H]3[C@@H](OC(C)=O)[C@]12O

InChI Identifier

InChI=1S/C22H29ClO9/c1-6-10-17(29-9(4)24)22(28)8(3)20(27)32-18(22)11(23)7(2)13-15(30-13)16(26)21(10,5)19-14(31-19)12(6)25/h6,8,10-19,25-26,28H,2H2,1,3-5H3/t6-,8+,10-,11+,12-,13-,14+,15-,16+,17-,18+,19+,21+,22-/m1/s1

InChI Key

SJZPSOOIOQXIIP-CECLVVHISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Briareum excavatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	0.032	ChemAxon
pKa (Strongest Acidic)	12.33	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.56 m³·mol⁻¹	ChemAxon
Polarizability	45.37 Å³	ChemAxon
Number of Rings	5	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

8871152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100993414

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate (NP0297245)

MOL for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

3D MOL for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

3D SDF for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

3D-SDF for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

PDB for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

3D PDB for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

SMILES for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

INCHI for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

Structure for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)

3D Structure for NP0297245 ((1s,2r,3s,5r,7s,8r,11r,12r,13r,14s,15r,16r,17s,19r)-7-chloro-2,12,16-trihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-13-yl acetate)