NP-MRD: Showing NP-Card for methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate (NP0197394)

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Record Information

Version

2.0

Created at

2022-09-04 15:39:00 UTC

Updated at

2022-09-04 15:39:00 UTC

NP-MRD ID

NP0197394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate

Description

Lopholide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate is found in Leptogorgia alba. Based on a literature review very few articles have been published on lopholide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217392D          

 32 36  0  0  1  0            999 V2000
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029    2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    2.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668    1.4868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690   -0.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063    0.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7113    2.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6430    1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2649   -1.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452   -0.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7274   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.2851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9697   -0.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019    0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.1051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2255    0.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281    0.5054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6976    1.8956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1310    2.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    2.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 20 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
  4 32  1  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
   -1.5295    3.6350    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    2.4309    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.8247    2.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    1.7601   -0.0694 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1633    1.7967    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    0.6281   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.5732   -0.3527 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2978   -1.4972   -0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -0.8295   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2608    0.5075   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806    1.6039   -1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9155    2.7985   -0.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423    1.3205   -1.5129 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192    2.3019   -1.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242   -2.8534   -0.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1923   -3.9265   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395   -3.1163    0.4541 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4156   -2.7960    1.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -3.7367    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511   -3.1947    1.0542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6728   -3.3961    0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -2.2227   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8583   -2.0875   -1.1170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -1.1198    0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4684   -1.2304    2.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3965   -1.7270    1.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3715    0.2652    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3821    0.4381   -0.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3865    1.3612   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4017    1.4824   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4555    2.1171    0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    0.5130   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    4.1280   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000    4.0914    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    2.3991    3.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888    0.7953    2.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0227    2.0312    2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    2.5031   -0.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043    1.8775    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130    2.7240   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409   -1.3067   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    1.7576   -1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4791    2.9292   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2091    2.8881   -2.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854   -3.1858   -1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5631   -3.0269    2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288   -3.4731    2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7648   -1.7906    2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1769   -4.8428    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380   -3.6285   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596   -3.6937    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -1.2476    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5899    1.0027    0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3471    1.0206   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    0.8787   -2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5306    2.5455   -2.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1535    0.5704   -1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4266   -0.4243   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  6  2  0
  6  5  1  0
  5  4  1  0
  4 32  1  0
 32 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 24  1  0
 24 25  1  1
 25 26  1  0
 26 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  1
 17 16  1  0
 16 15  1  0
 15  8  1  0
  8  7  1  0
  8  9  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  9 10  1  0
  7  6  1  0
 26 24  1  0
 15 17  1  0
 22 24  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
  5 39  1  0
  5 40  1  0
  4 38  1  6
 32 57  1  0
 32 58  1  0
 27 53  1  1
 30 54  1  0
 30 55  1  0
 30 56  1  0
 26 52  1  1
 20 51  1  1
 19 49  1  0
 19 50  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 15 45  1  6
  9 41  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652309042217392D          

 32 36  0  0  1  0            999 V2000
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029    2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    2.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668    1.4868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690   -0.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063    0.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7113    2.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6430    1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2649   -1.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452   -0.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7274   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.2851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9697   -0.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019    0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.1051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2255    0.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281    0.5054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6976    1.8956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1310    2.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    2.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 20 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
  4 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2C[C@@H](C[C@@H](OC(C)=O)[C@]34O[C@H]3[C@H](C[C@@]3(C)O[C@@H]3C(O2)=C1)OC4=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O9/c1-10(2)12-6-14-13(20(25)27-5)8-15(29-14)18-22(4,31-18)9-16-19-23(32-19,21(26)30-16)17(7-12)28-11(3)24/h8,12,16-19H,1,6-7,9H2,2-5H3/t12-,16-,17+,18+,19-,22+,23-/m0/s1

> <INCHI_KEY>
QFVLPFJFNHETFU-XFWUOHGQSA-N

> <FORMULA>
C23H26O9

> <MOLECULAR_WEIGHT>
446.452

> <EXACT_MASS>
446.157682417

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.70890962908584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2R,4R,10S,12R,14S,15S)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-diene-7-carboxylate

> <JCHEM_LOGP>
2.017463107666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.026524381242097

> <JCHEM_POLAR_SURFACE_AREA>
117.10000000000002

> <JCHEM_REFRACTIVITY>
107.05869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,4R,10S,12R,14S,15S)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-diene-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.841   5.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899   4.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.397   4.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.458   2.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.956   3.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.014   2.012   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.602   0.378   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.262  -1.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.638   0.123   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.512   1.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.680   2.662   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.394   4.175   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      16.134   2.152   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.301   3.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.143  -2.071   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.828  -2.873   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.791  -1.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.825  -2.532   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.136  -1.652   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.078  -0.532   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.544  -0.408   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.187   1.090   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.737   1.608   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.462   2.063   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.021   0.587   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.519   0.943   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.902   3.539   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.845   4.658   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.346   4.302   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.906   2.826   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.289   5.421   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.400   3.895   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15   17                                                       
CONECT   17   16   15   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24   26                                                       
CONECT   26   25   20   24                                                  
CONECT   27   24   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27    4                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₉

Average Mass

446.4520 Da

Monoisotopic Mass

446.15768 Da

IUPAC Name

methyl (1S,2R,4R,10S,12R,14S,15S)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-diene-7-carboxylate

Traditional Name

methyl (1S,2R,4R,10S,12R,14S,15S)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-diene-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C[C@@H](C[C@@H](OC(C)=O)[C@]34O[C@H]3[C@H](C[C@@]3(C)O[C@@H]3C(O2)=C1)OC4=O)C(C)=C

InChI Identifier

InChI=1S/C23H26O9/c1-10(2)12-6-14-13(20(25)27-5)8-15(29-14)18-22(4,31-18)9-16-19-23(32-19,21(26)30-16)17(7-12)28-11(3)24/h8,12,16-19H,1,6-7,9H2,2-5H3/t12-,16-,17+,18+,19-,22+,23-/m0/s1

InChI Key

QFVLPFJFNHETFU-XFWUOHGQSA-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
Leptogorgia alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Furoic acid ester
Tricarboxylic acid or derivatives
Furoic acid or derivatives
Furan-3-carboxylic acid ester
Furan-3-carboxylic acid or derivatives
Para-dioxane
Gamma butyrolactone
Furan
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.02	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	117.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.06 m³·mol⁻¹	ChemAxon
Polarizability	44.71 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

C00041639

Chemspider ID

24692957

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583998

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate (NP0197394)

MOL for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

3D MOL for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

3D SDF for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

3D-SDF for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

PDB for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

3D PDB for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

SMILES for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

INCHI for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

Structure for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)

3D Structure for NP0197394 (methyl (1s,2r,4r,10s,12r,14s,15s)-2-(acetyloxy)-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-diene-7-carboxylate)