NP-MRD: Showing NP-Card for methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate (NP0170706)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 06:56:33 UTC

Updated at

2022-09-03 06:56:33 UTC

NP-MRD ID

NP0170706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate

Description

Methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-15-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate is found in Dioscorea bulbifera. Based on a literature review very few articles have been published on methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-15-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208562D          

 33 37  0  0  1  0            999 V2000
   -1.8738   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -0.1989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -1.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.3921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4004    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796    1.5450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.7831    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5163    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4076    1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.2907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3003    1.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1253    1.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3763    2.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7064    3.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414    2.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    0.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943   -0.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -0.0490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1659   -0.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4217   -0.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -0.5454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6296   -1.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5933   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -2.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    0.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3408   -0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113   -0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
  5 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  7 33  1  1  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
    5.4922   -0.7043    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500   -0.3495    0.4525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047   -1.1978   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -2.4087   -0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.8059   -0.7860 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5074   -2.1254   -1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8602   -2.8568   -0.1554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4833   -2.1514    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.6622   -0.0031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2404   -0.0427    0.9035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1330   -0.3658    2.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779   -0.3584    0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -0.0441   -0.9359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4188   -0.2796   -1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2039    0.1558   -2.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4692   -0.3365   -1.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4827   -1.0213   -0.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613   -1.0031   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6399    1.3065   -1.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568    1.8802   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    2.7805   -1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    1.4625    0.7787 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0757    1.9787    1.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2464    1.9520    1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913    1.1386    0.5877 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9482    1.7933   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069    2.4974   -0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5655    3.1127   -1.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7493    2.6003    0.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534   -0.2844    0.3538 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5561   -1.2237    1.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -0.8198    2.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846   -2.5541    1.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6856   -0.0687    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2719   -0.4270    0.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903   -1.7817    1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1519   -0.1272   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118   -2.7512   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7380   -1.9604   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -3.9220   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.4957   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152   -2.5332    0.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -0.3221   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    0.4080    2.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745   -0.2577    2.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386   -1.3821    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.3007    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521   -1.4036    0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738   -0.6395   -1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8464    0.7464   -3.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3318   -0.1858   -2.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0085   -1.5113    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978    2.9567    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    2.0785    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    3.0013    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902    1.2641    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647    2.6072   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578    3.1900   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    4.1535   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 25 30  1  0
 30 31  1  1
 31 32  2  0
 31 33  1  0
 13 14  1  0
 14 18  2  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 30  5  1  0
 15 14  1  0
 33  7  1  0
 30  9  1  0
 22 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  6
  8 41  1  0
  8 42  1  0
  9 43  1  6
 11 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  6
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  1
 28 57  1  0
 28 58  1  0
 28 59  1  0
 18 52  1  0
 16 51  1  0
 15 50  1  0
M  END


  Mrv1652309032208562D          

 33 37  0  0  1  0            999 V2000
   -1.8738   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -0.1989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -1.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.3921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4004    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796    1.5450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.7831    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5163    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4076    1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.2907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3003    1.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1253    1.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3763    2.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7064    3.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414    2.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    0.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943   -0.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -0.0490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1659   -0.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4217   -0.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -0.5454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6296   -1.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5933   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -2.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    0.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3408   -0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113   -0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
  5 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  7 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0170706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1C[C@@H]2C[C@H]3[C@]4(C)C[C@H](OC(=O)[C@]4(O)C[C@H](OC(C)=O)[C@]13C(=O)O2)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O10/c1-11(24)31-17-9-22(28)19(26)33-15(12-4-5-30-10-12)8-21(22,2)16-7-13-6-14(18(25)29-3)23(16,17)20(27)32-13/h4-5,10,13-17,28H,6-9H2,1-3H3/t13-,14-,15+,16+,17+,21+,22-,23+/m1/s1

> <INCHI_KEY>
ZCLDOCOCRYIXPM-FBYGNPFPSA-N

> <FORMULA>
C23H26O10

> <MOLECULAR_WEIGHT>
462.451

> <EXACT_MASS>
462.152597037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.49338249391977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-15-carboxylate

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
0.6017453206666654

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.676589561452335

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.926796129027922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888539629782333

> <JCHEM_POLAR_SURFACE_AREA>
138.57

> <JCHEM_REFRACTIVITY>
106.60229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-15-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.498  -1.644   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.631  -0.371   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.047  -0.489   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.148  -2.147   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.194   0.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.747   1.974   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.522   2.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104   2.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.079   1.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.697   1.312   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.494   2.880   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.596   2.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.128   2.409   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.027   3.660   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.567   3.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.036   5.135   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.785   6.033   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.544   5.122   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.762   1.006   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.863  -0.245   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.829  -1.502   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.331  -0.092   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.910  -1.651   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.521  -1.452   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.995  -1.018   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.042  -2.691   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.974  -4.303   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.274  -5.129   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.609  -5.017   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.946   0.271   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.636  -0.294   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.768  -1.415   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.044   1.386   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   13   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25    5    9   31                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0,.0,]hexadecane-15-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₆O₁₀

Average Mass

462.4510 Da

Monoisotopic Mass

462.15260 Da

IUPAC Name

methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-15-carboxylate

Traditional Name

methyl (1R,2S,4S,7S,9S,10S,12S,15S)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-15-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1C[C@@H]2C[C@H]3[C@]4(C)C[C@H](OC(=O)[C@]4(O)C[C@H](OC(C)=O)[C@]13C(=O)O2)C1=COC=C1

InChI Identifier

InChI=1S/C23H26O10/c1-11(24)31-17-9-22(28)19(26)33-15(12-4-5-30-10-12)8-21(22,2)16-7-13-6-14(18(25)29-3)23(16,17)20(27)32-13/h4-5,10,13-17,28H,6-9H2,1-3H3/t13-,14-,15+,16+,17+,21+,22-,23+/m1/s1

InChI Key

ZCLDOCOCRYIXPM-FBYGNPFPSA-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
Dioscorea bulbifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.3	ALOGPS
logP	0.6	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.6 m³·mol⁻¹	ChemAxon
Polarizability	44.49 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162864818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate (NP0170706)

MOL for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

3D MOL for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

3D SDF for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

3D-SDF for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

PDB for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

3D PDB for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

SMILES for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

INCHI for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

Structure for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)

3D Structure for NP0170706 (methyl (1r,2s,4s,7s,9s,10s,12s,15s)-2-(acetyloxy)-7-(furan-3-yl)-4-hydroxy-9-methyl-5,14-dioxo-6,13-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-15-carboxylate)