NP-MRD: Showing NP-Card for (1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid (NP0285387)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 13:32:38 UTC

Updated at

2022-09-09 13:32:38 UTC

NP-MRD ID

NP0285387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid

Description

4-Epi-scopadulcic acid B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid is found in Scoparia dulcis. (1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid was first documented in 2003 (PMID: 12880314). Based on a literature review very few articles have been published on 4-epi-scopadulcic acid B (PMID: 24955889).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215322D          

 32 36  0  0  1  0            999 V2000
    3.6732   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.3631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6111   -0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2627   -0.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011    1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    1.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.3976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2801    1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -0.3319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5824   -1.0401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9715   -1.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2315   -1.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1852   -2.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097   -2.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3989   -3.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -3.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -3.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547   -1.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -0.2774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4958   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    0.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    1.1512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1809    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    0.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1261    0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  6  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  6  0  0  0
 27 32  1  0  0  0  0
M  END

     RDKit          2D

 66 70  0  0  0  0  0  0  0  0999 V2000
   -3.7777   -4.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -4.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637   -6.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8246   -7.0658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9927   -5.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2997   -4.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865   -2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2733   -1.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115   -3.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171   -2.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1176   -3.6868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5925   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5668   -2.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0931   -5.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5680   -5.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0686   -7.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0943   -8.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6194   -7.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1188   -6.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303   -0.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463   -0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    1.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    2.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    3.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578    2.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731   -4.3817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0252   -5.7433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956   -2.7685    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252   -8.4798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -6.3904    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -6.6038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746   -4.2149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8252   -5.8934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -1.9751    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7248   -3.4144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527   -1.2410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474   -2.4221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -0.0503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038   -3.7728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0965   -2.0254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5422   -4.5072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5434   -7.3352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5949   -9.6163    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -9.0694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216   -6.6064    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1051   -1.0464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800    0.4632    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599    0.8750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524    2.9405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667    1.7457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3213    4.0667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844    2.1766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016    3.2741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907    1.0037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047   -0.8603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933   -1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -2.6908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177    0.9588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    2.0982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 31 30  1  1
 31 32  1  0
 31 23  1  0
 23 22  1  0
 22 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 11  1  0
 11  2  1  0
  2  1  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  2  3  1  6
  3  5  1  0
  3  4  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 32 27  1  0
 21 16  1  0
  9 11  1  0
 25 27  1  0
  9 31  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 32 65  1  0
 32 66  1  0
 23 55  1  6
 22 53  1  0
 22 54  1  0
 12 47  1  1
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 11 46  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
  5 36  1  0
 24 56  1  0
 24 57  1  0
M  END


  Mrv1652309092215322D          

 32 36  0  0  1  0            999 V2000
    3.6732   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.3631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6111   -0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2627   -0.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011    1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    1.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.3976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2801    1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -0.3319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5824   -1.0401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9715   -1.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2315   -1.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1852   -2.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097   -2.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3989   -3.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -3.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -3.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547   -1.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -0.2774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4958   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    0.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    1.1512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1809    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    0.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1261    0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  6  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  6  0  0  0
 27 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@]3(C1)[C@@H](C[C@@H](OC(=O)C1=CC=CC=C1)[C@H]1[C@](C)(CCC[C@]31C)C(O)=O)CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O5/c1-24-12-13-27(16-24)18(15-20(24)28)14-19(32-22(29)17-8-5-4-6-9-17)21-25(2,23(30)31)10-7-11-26(21,27)3/h4-6,8-9,18-19,21H,7,10-16H2,1-3H3,(H,30,31)/t18-,19+,21-,24+,25-,26-,27-/m0/s1

> <INCHI_KEY>
DQBAMWXMUCSBLO-CADUKSBLSA-N

> <FORMULA>
C27H34O5

> <MOLECULAR_WEIGHT>
438.564

> <EXACT_MASS>
438.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
37.1770953731855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,7R,8R,10S,13R)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecane-6-carboxylic acid

> <JCHEM_LOGP>
5.687756289333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.947966345179704

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.233314266855587

> <JCHEM_PKA_STRONGEST_BASIC>
-6.796850871870616

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
119.62029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7R,8R,10S,13R)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecane-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.857  -2.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.181  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.607  -1.259   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.824  -0.314   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.817  -2.785   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.001   0.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.282   1.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.743   2.046   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.923   0.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.256   2.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.642  -0.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.820  -1.942   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.547  -3.299   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.086  -3.349   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.899  -2.041   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.812  -4.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.352  -4.757   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.078  -6.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.265  -7.423   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.726  -7.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.999  -6.015   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.275  -1.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.543  -0.518   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.926  -0.644   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.116   0.732   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.424   0.712   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.901   2.149   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.338   3.065   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.023   3.311   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.488   2.594   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.341   0.922   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.102   1.463   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   11                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   12   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   32                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23    9   32                                             
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-Epi-scopadulcate b	Generator

Chemical Formula

C₂₇H₃₄O₅

Average Mass

438.5640 Da

Monoisotopic Mass

438.24062 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@]3(C1)[C@@H](C[C@@H](OC(=O)C1=CC=CC=C1)[C@H]1[C@](C)(CCC[C@]31C)C(O)=O)CC2=O

InChI Identifier

InChI=1S/C27H34O5/c1-24-12-13-27(16-24)18(15-20(24)28)14-19(32-22(29)17-8-5-4-6-9-17)21-25(2,23(30)31)10-7-11-26(21,27)3/h4-6,8-9,18-19,21H,7,10-16H2,1-3H3,(H,30,31)/t18-,19+,21-,24+,25-,26-,27-/m0/s1

InChI Key

DQBAMWXMUCSBLO-CADUKSBLSA-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
Scoparia dulcis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029527

Chemspider ID

9092409

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10917156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ahsan M, Islam SK, Gray AI, Stimson WH: Cytotoxic diterpenes from Scoparia dulcis. J Nat Prod. 2003 Jul;66(7):958-61. doi: 10.1021/np020356j. [PubMed:12880314 ]
Liu Q, Yang QM, Hu HJ, Yang L, Yang YB, Chou GX, Wang ZT: Bioactive diterpenoids and flavonoids from the aerial parts of Scoparia dulcis. J Nat Prod. 2014 Jul 25;77(7):1594-600. doi: 10.1021/np500150f. Epub 2014 Jun 23. [PubMed:24955889 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid (NP0285387)

MOL for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

3D MOL for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

3D SDF for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

3D-SDF for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

PDB for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

3D PDB for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

SMILES for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

INCHI for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

Structure for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)

3D Structure for NP0285387 ((1s,2s,6s,7r,8r,10s,13r)-8-(benzoyloxy)-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecane-6-carboxylic acid)